Lysergamides: Difference between revisions
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The simplest lysergamides are [[ergine]] (lysergic acid amide; LSA) and [[isoergine]] (iso-lysergic acid amide; iso-LSA). In terms of [[pharmacology]], the lysergamides include numerous [[serotonin]] and [[dopamine]] [[receptor (biochemistry)|receptor]] [[agonist]]s, most notably the [[psychedelic drug]] [[lysergic acid diethylamide]] (LSD) but also a number of [[pharmaceutical drug]]s like [[ergometrine]], [[methylergometrine]], [[methysergide]], and [[cabergoline]].<ref name="US2997470">{{cite patent | country = US | number = 2997470 | status = patent | title = Lysergic Acid Amides | pubdate = 1956-03-05 | gdate = 1961-08-22 | inventor = Pioch RP}}</ref><ref name="HoffmanNichols1985">{{cite journal | vauthors = Hoffman AJ, Nichols DE | title = Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives | journal = Journal of Medicinal Chemistry | volume = 28 | issue = 9 | pages = 1252–1255 | date = September 1985 | pmid = 4032428 | doi = 10.1021/jm00147a022}}</ref><ref name="HuangMarona-LewickaPfaff1994">{{cite journal | vauthors = Huang X, Marona-Lewicka D, Pfaff RC, Nichols DE | title = Drug discrimination and receptor binding studies of N-isopropyl lysergamide derivatives | journal = Pharmacology, Biochemistry, and Behavior | volume = 47 | issue = 3 | pages = 667–673 | date = March 1994 | pmid = 8208787 | doi = 10.1016/0091-3057(94)90172-4 | s2cid = 16490010}}</ref><ref name="WattsLawlerFox1995">{{cite journal | vauthors = Watts VJ, Lawler CP, Fox DR, Neve KA, Nichols DE, Mailman RB | title = LSD and structural analogs: pharmacological evaluation at D1 dopamine receptors | journal = Psychopharmacology | volume = 118 | issue = 4 | pages = 401–409 | date = April 1995 | pmid = 7568626 | doi = 10.1007/BF02245940 | s2cid = 21484356}}</ref><ref name="NicholsFrescasMarona-Lewicka2002">{{cite journal | vauthors = Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM | title = Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD) | journal = Journal of Medicinal Chemistry | volume = 45 | issue = 19 | pages = 4344–4349 | date = September 2002 | pmid = 12213075 | doi = 10.1021/jm020153s}}</ref><ref name="Schiff2006">{{cite journal | vauthors = Schiff PL | title = Ergot and its alkaloids | journal = American Journal of Pharmaceutical Education | volume = 70 | issue = 5 | page = 98 | date = October 2006 | pmid = 17149427 | doi = 10.5688/aj700598 | doi-broken-date = 2024-11-22 | pmc = 1637017}}</ref><ref name="PassieHalpernStichtenoth2008">{{cite journal | vauthors = Passie T, Halpern JH, Stichtenoth DO, Emrich HM, Hintzen A | title = The pharmacology of lysergic acid diethylamide: a review | journal = CNS Neuroscience & Therapeutics | year = 2008 | volume = 14 | issue = 4 | pages = 295–314 | pmid = 19040555 | doi = 10.1111/j.1755-5949.2008.00059.x | pmc = 6494066}}</ref><ref name="BrandtKavanaghWestphal2016">{{cite journal | vauthors = Brandt SD, Kavanagh PV, Westphal F, Stratford A, Elliott SP, Hoang K, Wallach J, Halberstadt AL | title = Return of the lysergamides. Part I: Analytical and behavioural characterization of 1-propionyl-d-lysergic acid diethylamide (1P-LSD) | journal = Drug Testing and Analysis | volume = 8 | issue = 9 | pages = 891–902 | date = September 2016 | pmid = 26456305 | doi = 10.1002/dta.1884 | pmc = 4829483}}</ref><ref name="BrandtKavanaghWestphal2017a">{{cite journal | vauthors = Brandt SD, Kavanagh PV, Westphal F, Elliott SP, Wallach J, Colestock T, Burrow TE, Chapman SJ, Stratford A, Nichols DE, Halberstadt AL | title = Return of the lysergamides. Part II: Analytical and behavioural characterization of N<sup>6</sup> -allyl-6-norlysergic acid diethylamide (AL-LAD) and (2'S,4'S)-lysergic acid 2,4-dimethylazetidide (LSZ) | journal = Drug Testing and Analysis | volume = 9 | issue = 1 | pages = 38–50 | date = January 2017 | pmid = 27265891 | doi = 10.1002/dta.1985 | pmc = 5411264}}</ref><ref name="BrandtKavanaghWestphal2017b">{{cite journal | vauthors = Brandt SD, Kavanagh PV, Westphal F, Elliott SP, Wallach J, Stratford A, Nichols DE, Halberstadt AL | title = Return of the lysergamides. Part III: Analytical characterization of N<sup>6</sup> -ethyl-6-norlysergic acid diethylamide (ETH-LAD) and 1-propionyl ETH-LAD (1P-ETH-LAD) | journal = Drug Testing and Analysis | volume = 9 | issue = 10 | pages = 1641–1649 | date = October 2017 | pmid = 28342178 | doi = 10.1002/dta.2196 | pmc = 6230477}}</ref><ref name="BrandtKavanaghTwamley2018">{{cite journal | vauthors = Brandt SD, Kavanagh PV, Twamley B, Westphal F, Elliott SP, Wallach J, Stratford A, Klein LM, McCorvy JD, Nichols DE, Halberstadt AL | title = Return of the lysergamides. Part IV: Analytical and pharmacological characterization of lysergic acid morpholide (LSM-775) | journal = Drug Testing and Analysis | volume = 10 | issue = 2 | pages = 310–322 | date = February 2018 | pmid = 28585392 | doi = 10.1002/dta.2222 | pmc = 6230476}}</ref><ref name="BrandtKavanaghWestphal2019">{{cite journal | vauthors = Brandt SD, Kavanagh PV, Westphal F, Stratford A, Elliott SP, Dowling G, Wallach J, Halberstadt AL | title = Return of the lysergamides. Part V: Analytical and behavioural characterization of 1-butanoyl-d-lysergic acid diethylamide (1B-LSD) | journal = Drug Testing and Analysis | volume = 11 | issue = 8 | pages = 1122–1133 | date = August 2019 | pmid = 31083768 | doi = 10.1002/dta.2613 | pmc = 6899222}}</ref><ref name="HalberstadtKleinChatha2019">{{cite journal | vauthors = Halberstadt AL, Klein LM, Chatha M, Valenzuela LB, Stratford A, Wallach J, Nichols DE, Brandt SD | title = Pharmacological characterization of the LSD analog N-ethyl-N-cyclopropyl lysergamide (ECPLA) | journal = Psychopharmacology | volume = 236 | issue = 2 | pages = 799–808 | date = February 2019 | pmid = 30298278 | doi = 10.1007/s00213-018-5055-9 | pmc = 6848745}}</ref> Various analogues of LSD, such as the psychedelics [[ALD-52]] (1A-LSD), [[ETH-LAD]], [[LSZ]], and [[1P-LSD]] and the non-hallucinogenic [[2-bromo-LSD]] (BOL-148), have also been developed. [[Ergopeptine]]s like [[ergotamine]], [[dihydroergotamine]], and [[bromocriptine]] are also lysergamides, but with addition of a small [[peptide]] moiety at the amide. Close analogues of lysergamides that are not technically lysergamides themselves include [[lisuride]], [[terguride]], [[bromerguride]], and [[JRT (drug)|JRT]]. | The simplest lysergamides are [[ergine]] (lysergic acid amide; LSA) and [[isoergine]] (iso-lysergic acid amide; iso-LSA). In terms of [[pharmacology]], the lysergamides include numerous [[serotonin]] and [[dopamine]] [[receptor (biochemistry)|receptor]] [[agonist]]s, most notably the [[psychedelic drug]] [[lysergic acid diethylamide]] (LSD) but also a number of [[pharmaceutical drug]]s like [[ergometrine]], [[methylergometrine]], [[methysergide]], and [[cabergoline]].<ref name="US2997470">{{cite patent | country = US | number = 2997470 | status = patent | title = Lysergic Acid Amides | pubdate = 1956-03-05 | gdate = 1961-08-22 | inventor = Pioch RP}}</ref><ref name="HoffmanNichols1985">{{cite journal | vauthors = Hoffman AJ, Nichols DE | title = Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives | journal = Journal of Medicinal Chemistry | volume = 28 | issue = 9 | pages = 1252–1255 | date = September 1985 | pmid = 4032428 | doi = 10.1021/jm00147a022}}</ref><ref name="HuangMarona-LewickaPfaff1994">{{cite journal | vauthors = Huang X, Marona-Lewicka D, Pfaff RC, Nichols DE | title = Drug discrimination and receptor binding studies of N-isopropyl lysergamide derivatives | journal = Pharmacology, Biochemistry, and Behavior | volume = 47 | issue = 3 | pages = 667–673 | date = March 1994 | pmid = 8208787 | doi = 10.1016/0091-3057(94)90172-4 | s2cid = 16490010}}</ref><ref name="WattsLawlerFox1995">{{cite journal | vauthors = Watts VJ, Lawler CP, Fox DR, Neve KA, Nichols DE, Mailman RB | title = LSD and structural analogs: pharmacological evaluation at D1 dopamine receptors | journal = Psychopharmacology | volume = 118 | issue = 4 | pages = 401–409 | date = April 1995 | pmid = 7568626 | doi = 10.1007/BF02245940 | s2cid = 21484356}}</ref><ref name="NicholsFrescasMarona-Lewicka2002">{{cite journal | vauthors = Nichols DE, Frescas S, Marona-Lewicka D, Kurrasch-Orbaugh DM | title = Lysergamides of isomeric 2,4-dimethylazetidines map the binding orientation of the diethylamide moiety in the potent hallucinogenic agent N,N-diethyllysergamide (LSD) | journal = Journal of Medicinal Chemistry | volume = 45 | issue = 19 | pages = 4344–4349 | date = September 2002 | pmid = 12213075 | doi = 10.1021/jm020153s}}</ref><ref name="Schiff2006">{{cite journal | vauthors = Schiff PL | title = Ergot and its alkaloids | journal = American Journal of Pharmaceutical Education | volume = 70 | issue = 5 | page = 98 | date = October 2006 | pmid = 17149427 | doi = 10.5688/aj700598 | doi-broken-date = 2024-11-22 | pmc = 1637017}}</ref><ref name="PassieHalpernStichtenoth2008">{{cite journal | vauthors = Passie T, Halpern JH, Stichtenoth DO, Emrich HM, Hintzen A | title = The pharmacology of lysergic acid diethylamide: a review | journal = CNS Neuroscience & Therapeutics | year = 2008 | volume = 14 | issue = 4 | pages = 295–314 | pmid = 19040555 | doi = 10.1111/j.1755-5949.2008.00059.x | pmc = 6494066}}</ref><ref name="BrandtKavanaghWestphal2016">{{cite journal | vauthors = Brandt SD, Kavanagh PV, Westphal F, Stratford A, Elliott SP, Hoang K, Wallach J, Halberstadt AL | title = Return of the lysergamides. Part I: Analytical and behavioural characterization of 1-propionyl-d-lysergic acid diethylamide (1P-LSD) | journal = Drug Testing and Analysis | volume = 8 | issue = 9 | pages = 891–902 | date = September 2016 | pmid = 26456305 | doi = 10.1002/dta.1884 | pmc = 4829483}}</ref><ref name="BrandtKavanaghWestphal2017a">{{cite journal | vauthors = Brandt SD, Kavanagh PV, Westphal F, Elliott SP, Wallach J, Colestock T, Burrow TE, Chapman SJ, Stratford A, Nichols DE, Halberstadt AL | title = Return of the lysergamides. Part II: Analytical and behavioural characterization of N<sup>6</sup> -allyl-6-norlysergic acid diethylamide (AL-LAD) and (2'S,4'S)-lysergic acid 2,4-dimethylazetidide (LSZ) | journal = Drug Testing and Analysis | volume = 9 | issue = 1 | pages = 38–50 | date = January 2017 | pmid = 27265891 | doi = 10.1002/dta.1985 | pmc = 5411264}}</ref><ref name="BrandtKavanaghWestphal2017b">{{cite journal | vauthors = Brandt SD, Kavanagh PV, Westphal F, Elliott SP, Wallach J, Stratford A, Nichols DE, Halberstadt AL | title = Return of the lysergamides. Part III: Analytical characterization of N<sup>6</sup> -ethyl-6-norlysergic acid diethylamide (ETH-LAD) and 1-propionyl ETH-LAD (1P-ETH-LAD) | journal = Drug Testing and Analysis | volume = 9 | issue = 10 | pages = 1641–1649 | date = October 2017 | pmid = 28342178 | doi = 10.1002/dta.2196 | pmc = 6230477}}</ref><ref name="BrandtKavanaghTwamley2018">{{cite journal | vauthors = Brandt SD, Kavanagh PV, Twamley B, Westphal F, Elliott SP, Wallach J, Stratford A, Klein LM, McCorvy JD, Nichols DE, Halberstadt AL | title = Return of the lysergamides. Part IV: Analytical and pharmacological characterization of lysergic acid morpholide (LSM-775) | journal = Drug Testing and Analysis | volume = 10 | issue = 2 | pages = 310–322 | date = February 2018 | pmid = 28585392 | doi = 10.1002/dta.2222 | pmc = 6230476}}</ref><ref name="BrandtKavanaghWestphal2019">{{cite journal | vauthors = Brandt SD, Kavanagh PV, Westphal F, Stratford A, Elliott SP, Dowling G, Wallach J, Halberstadt AL | title = Return of the lysergamides. Part V: Analytical and behavioural characterization of 1-butanoyl-d-lysergic acid diethylamide (1B-LSD) | journal = Drug Testing and Analysis | volume = 11 | issue = 8 | pages = 1122–1133 | date = August 2019 | pmid = 31083768 | doi = 10.1002/dta.2613 | pmc = 6899222}}</ref><ref name="HalberstadtKleinChatha2019">{{cite journal | vauthors = Halberstadt AL, Klein LM, Chatha M, Valenzuela LB, Stratford A, Wallach J, Nichols DE, Brandt SD | title = Pharmacological characterization of the LSD analog N-ethyl-N-cyclopropyl lysergamide (ECPLA) | journal = Psychopharmacology | volume = 236 | issue = 2 | pages = 799–808 | date = February 2019 | pmid = 30298278 | doi = 10.1007/s00213-018-5055-9 | pmc = 6848745}}</ref> Various analogues of LSD, such as the psychedelics [[ALD-52]] (1A-LSD), [[ETH-LAD]], [[LSZ]], and [[1P-LSD]] and the non-hallucinogenic [[2-bromo-LSD]] (BOL-148), have also been developed. [[Ergopeptine]]s like [[ergotamine]], [[dihydroergotamine]], and [[bromocriptine]] are also lysergamides, but with addition of a small [[peptide]] moiety at the amide. Close analogues of lysergamides that are not technically lysergamides themselves include [[lisuride]], [[terguride]], [[bromerguride]], and [[JRT (drug)|JRT]]. | ||
Lysergamides were first discovered and described in the 1930s.<ref name="BrimblecombePinder1975" /><ref name="Rav2011" /><ref name="SmithTimmis1932" /> | |||
[[Partial lysergamide|Simplified or partial ergolines and lysergamides]], such as [[NDTDI]], [[DEMPDHPCA]], and [[N-DEAOP-NMT|''N''-DEAOP-NMT]], are also known.<ref name="Shulgin1976">{{cite book | veditors=Gordon M | title=Psychopharmacological Agents: Use, Misuse and Abuse | series=Medicinal Chemistry: A Series of Monographs | volume=4 | last=Shulgin | first=Alexander T. | chapter=Psychotomimetic Agents | date=1976 | isbn=978-0-12-290559-9 | doi=10.1016/b978-0-12-290559-9.50011-9 | pages=59–146 | publisher=Academic Press | url=https://bitnest.netfirms.com/external/10.1016/B978-0-12-290559-9.50011-9 | quote=The largest number of structural analogs of LSD that have been prepared involve the opening of one or more of the rings of the parent lysergic acid system. The compounds with the piperidine ring (ring D) opened [see (I)] are encountered as natural products in the several Convolvulaceae discussed in Section II,B on ololiuqui. The opening of ring C (by cleavage of the 10-11 bond to the indole "4 position") results in a series of N-α-disubstituted tryptamines. Additionally, analogs are known with the indolic nitrogen replaced with sulfur (benzothiophenes) and with an aliphatic chain (tetralins). A recent review covers this chemistry (Campaigne and Knapp, 1971), but there is apparently no human psychopharmacology as yet known.}}</ref><ref name="Nichols1973">{{cite thesis | vauthors = [[David E. Nichols|Nichols DE]] | title = Potential Psychotomimetics: Bromomethoxyamphetamines and Structural Congeners of Lysergic Acid | date = May 1973 | publisher = [[University of Iowa]] | pages = 23 | oclc = 1194694085 | url = https://bitnest.netfirms.com/external/Theses/Nichols1973#page=32}}</ref><ref name="CampaigneKnapp1971">{{cite journal | vauthors = Campaigne E, Knapp DR | title = Structural analogs of lysergic acid | journal = J Pharm Sci | volume = 60 | issue = 6 | pages = 809–814 | date = June 1971 | pmid = 4942861 | doi = 10.1002/jps.2600600602 | url = }}</ref> | [[Partial lysergamide|Simplified or partial ergolines and lysergamides]], such as [[NDTDI]] (8,10-seco-LSD), [[DEMPDHPCA]], and [[N-DEAOP-NMT|''N''-DEAOP-NMT]], are also known.<ref name="Shulgin1976">{{cite book | veditors=Gordon M | title=Psychopharmacological Agents: Use, Misuse and Abuse | series=Medicinal Chemistry: A Series of Monographs | volume=4 | last=Shulgin | first=Alexander T. | chapter=Psychotomimetic Agents | date=1976 | isbn=978-0-12-290559-9 | doi=10.1016/b978-0-12-290559-9.50011-9 | pages=59–146 | publisher=Academic Press | url=https://bitnest.netfirms.com/external/10.1016/B978-0-12-290559-9.50011-9 | quote=The largest number of structural analogs of LSD that have been prepared involve the opening of one or more of the rings of the parent lysergic acid system. The compounds with the piperidine ring (ring D) opened [see (I)] are encountered as natural products in the several Convolvulaceae discussed in Section II,B on ololiuqui. The opening of ring C (by cleavage of the 10-11 bond to the indole "4 position") results in a series of N-α-disubstituted tryptamines. Additionally, analogs are known with the indolic nitrogen replaced with sulfur (benzothiophenes) and with an aliphatic chain (tetralins). A recent review covers this chemistry (Campaigne and Knapp, 1971), but there is apparently no human psychopharmacology as yet known.}}</ref><ref name="Nichols1973">{{cite thesis | vauthors = [[David E. Nichols|Nichols DE]] | title = Potential Psychotomimetics: Bromomethoxyamphetamines and Structural Congeners of Lysergic Acid | date = May 1973 | publisher = [[University of Iowa]] | pages = 23 | oclc = 1194694085 | url = https://bitnest.netfirms.com/external/Theses/Nichols1973#page=32}}</ref><ref name="CampaigneKnapp1971">{{cite journal | vauthors = Campaigne E, Knapp DR | title = Structural analogs of lysergic acid | journal = J Pharm Sci | volume = 60 | issue = 6 | pages = 809–814 | date = June 1971 | pmid = 4942861 | doi = 10.1002/jps.2600600602 | url = }}</ref> | ||
==Use and effects== | ==Use and effects== | ||
The [[Dosage (pharmacology)|dosage]]s, [[potency (pharmacology)|potencies]], [[duration of action|duration]]s, and effects of lysergamides have been reviewed by [[Alexander Shulgin]].<ref name="Shulgin2003">{{cite book | vauthors = Shulgin AT | chapter=Basic Pharmacology and Effects | pages=67–137 | veditors = Laing RR | title=Hallucinogens: A Forensic Drug Handbook | publisher=Elsevier Science | series=Forensic Drug Handbook Series | year=2003 | isbn=978-0-12-433951-4 | url=https://books.google.com/books?id=l1DrqgobbcwC | chapter-url=https://web.archive.org/web/20250223164514/https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6bb3a7499da8e9852b39cd4db16891147c83f5c6}}</ref><ref name="JacobShulgin1994">{{cite journal | vauthors = Jacob P, Shulgin AT | title = Structure-activity relationships of the classic hallucinogens and their analogs | journal = NIDA Res Monogr | volume = 146 | issue = | pages = 74–91 | date = 1994 | pmid = 8742795 | doi = | url = https:// | The [[Dosage (pharmacology)|dosage]]s, [[potency (pharmacology)|potencies]], [[duration of action|duration]]s, and effects of lysergamides have been reviewed by [[Alexander Shulgin]].<ref name="Shulgin2003">{{cite book | vauthors = Shulgin AT | chapter=Basic Pharmacology and Effects | pages=67–137 | veditors = Laing RR | title=Hallucinogens: A Forensic Drug Handbook | publisher=Elsevier Science | series=Forensic Drug Handbook Series | year=2003 | isbn=978-0-12-433951-4 | url=https://books.google.com/books?id=l1DrqgobbcwC | chapter-url=https://web.archive.org/web/20250223164514/https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6bb3a7499da8e9852b39cd4db16891147c83f5c6}}</ref><ref name="JacobShulgin1994">{{cite journal | vauthors = Jacob P, Shulgin AT | title = Structure-activity relationships of the classic hallucinogens and their analogs | journal = NIDA Res Monogr | volume = 146 | issue = | pages = 74–91 | date = 1994 | pmid = 8742795 | doi = | url = https://bitnest.netfirms.com/external/Books/NIDA146.74}}</ref><ref name="Shulgin1982">{{cite book |vauthors=Shulgin AT | chapter=Chemistry of Psychotomimetics | pages = 3–29 | veditors = Hoffmeister F, Stille G | title=Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs | series=Handbook of Experimental Pharmacology | publisher=Springer Berlin Heidelberg |location=Berlin |date=1982 | volume=55 / 3 |isbn=978-3-642-67772-4 | oclc = 8130916 | doi=10.1007/978-3-642-67770-0_1 | url = https://books.google.com/books?id=mrT8CAAAQBAJ | chapter-url = https://bitnest.netfirms.com/external/10.1007/978-3-642-67770-0_1}}</ref><ref name="Shulgin1980">{{cite book | author = Alexander T. Shulgin | chapter = Hallucinogens | pages = 1109–1137 | chapter-url = https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=6ac0c892ee380436f614d3aae0686ef617b2e0c5 | veditors = Burger A, Wolf ME | title = Burger's Medicinal Chemistry | edition = 4 | volume = 3 | date = 1980 | publisher = Wiley | location = New York | isbn = 978-0-471-01572-7 | oclc = 219960627 | url = https://books.google.com/books?id=2b3wAAAAMAAJ}}</ref><ref name="TiHKAL1997">{{cite book | author1 = [[Alexander T. Shulgin]] | author2 = [[Ann Shulgin]] | chapter = #26. LSD-25 Acid; Lysergide; D-Lysergic Acid Diethylamide; Meth-LAD; D-Lysergamide, N,N-Diethyl; N,N-Diethyl-D-Lysergamide; 9,10-Didehydro-N,N-Diethyl-6-Methylergoline-8b-Carboxamide | pages = 490–499 | chapter-url = https://www.erowid.org/library/books_online/tihkal/tihkal26.shtml | title = [[TiHKAL: The Continuation]] | publisher = Transform Press | date = 1997 | edition = 1st | location = Berkeley, CA | isbn = 978-0-9630096-9-2 | oclc = 38503252 | quote = The second major location of variations in the structure of LSD has been in the nature of the alkyl groups on the amide nitrogen atom. Some of these are Sandoz syntheses, some are from other research groups, and a few of them are found in nature. Some of these have been studied in man, and some have not. A few of the original clutch of Sandoz compounds have both 1-substituents and amide alkyl (R) group variations: [...] }}</ref> They have also been reviewed by [[Albert Hofmann]],<ref name="Hofmann1959">{{cite journal | vauthors = Hofmann A | title = Psychotomimetic Drugs: Chemical and Pharmacological Aspects | journal = Acta Physiol Pharmacol Neerl | volume = 8 | issue = | pages = 240–258 | date = June 1959 | pmid = 13852489 | doi = | url = https://www.samorini.it/doc1/alt_aut/ek/hofmann-psychotomimetic-drugs.pdf}}</ref> [[David E. Nichols]],<ref name="Nichols2018">{{cite book | vauthors = Nichols DE | title = Chemistry and Structure-Activity Relationships of Psychedelics | series = Current Topics in Behavioral Neurosciences | volume = 36 | pages = 1–43 | date = 2018 | pmid = 28401524 | doi = 10.1007/7854_2017_475 | isbn = 978-3-662-55878-2 | url = https://bitnest.netfirms.com/external/10.1007/7854_2017_475}}</ref> and other researchers.<ref name="RutschmannStadler1978">{{cite book | vauthors = Rutschmann J, Stadler PA | chapter=Chemical Background | veditors=Berde B, Schild HO | title=Ergot Alkaloids and Related Compounds | publisher=Springer Berlin Heidelberg | publication-place=Berlin, Heidelberg | date=1978 | isbn=978-3-642-66777-0 | doi=10.1007/978-3-642-66775-6_2 | pages=29–85 | series=Handbook of Experimental Pharmacology (HEP) | volume=49}}</ref><ref name="Mangner1978">{{cite thesis | vauthors = Mangner TJ | degree = Ph.D. | publisher = University of Michigan | title=Potential Psychotomimetic Antagonists. N,N-Diethyl-1-methyl-3-aryl-1,2,5,6-tetrahydropyridine-5-carboxamides | date=1978 | doi=10.7302/11268 | url=https://www.proquest.com/openview/f845a6810749d00f70305960adfde737/ | archive-url=https://web.archive.org/web/20250330031605/https://media.proquest.com/media/hms/ORIG/2/9yQxJ?cit%3Aauth=MANGNER%2C+THOMAS+JOSEPH&cit%3Atitle=POTENTIAL+PSYCHOTOMIMETIC+ANTAGONISTS.+N%2CN+...&cit%3Apub=ProQuest+Dissertations+and+Theses&cit%3Avol=&cit%3Aiss=&cit%3Apg=&cit%3Adate=1978&ic=true&cit%3Aprod=ProQuest+Dissertations+%26+Theses+Global&_a=ChgyMDI1MDMzMDAzMDAzNTMxOTo3ODkyMzgSBjEwNjkyNRoKT05FX1NFQVJDSCILNzYuMTc0LjAuNTcqBTE4NzUwMgkzMDI5MDU4NjE6DURvY3VtZW50SW1hZ2VCATBSBk9ubGluZVoCRlRiA1BGVGoAcgB6AIIBJVAtMTAxMDI2OC0xMDA1MS1DVVNUT01FUi1udWxsLTcwOTY2NDmSAQZPbmxpbmXKAW9Nb3ppbGxhLzUuMCAoV2luZG93cyBOVCAxMC4wOyBXaW42NDsgeDY0KSBBcHBsZVdlYktpdC81MzcuMzYgKEtIVE1MLCBsaWtlIEdlY2tvKSBDaHJvbWUvMTM0LjAuMC4wIFNhZmFyaS81MzcuMzbSARZEaXNzZXJ0YXRpb25zICYgVGhlc2VzmgIHUHJlUGFpZKoCK09TOkVNUy1NZWRpYUxpbmtzU2VydmljZS1nZXRNZWRpYVVybEZvckl0ZW3KAhNEaXNzZXJ0YXRpb24vVGhlc2lz0gIBWfICAPoCAU6CAwNXZWKKAxxDSUQ6MjAyNTAzMzAwMzAwMzUzMTk6NTcyNjc1&_s=QP3F3liRMGFAbHtX3wDWE8eO1gs%3D#page=22 | archive-date=30 March 2025 | quote = Table 1. Human psychotomimetic potencies of LSD analogs. [...]}}</ref><ref name="Fanchamps1978">{{cite book | vauthors = Fanchamps A | chapter=Some Compounds With Hallucinogenic Activity | veditors=Berde B, Schild HO | title=Ergot Alkaloids and Related Compounds | publisher=Springer Berlin Heidelberg | publication-place=Berlin, Heidelberg | date=1978 | isbn=978-3-642-66777-0 | doi=10.1007/978-3-642-66775-6_8 | pages=567–614 | series=Handbook of Experimental Pharmacology (HEP) | volume=49 | chapter-url=https://bibliography.maps.org/resources/download/8769#page=30 | archive-url=https://web.archive.org/web/20250330033128/https://bibliography.maps.org/resources/download/8769#page=30 | archive-date=30 March 2025 | quote = Table 2. Psychotomimetic activity and some pharmacodynamic effects of structural analogues of LSD [...]}}</ref><ref name="Rothlin1957">{{cite journal | vauthors = Rothlin E | title = Lysergic acid diethylamide and related substances | journal = Ann N Y Acad Sci | volume = 66 | issue = 3 | pages = 668–676 | date = March 1957 | pmid = 13425249 | doi = 10.1111/j.1749-6632.1957.tb40756.x | bibcode = 1957NYASA..66..668R | url = https://bibliography.maps.org/resources/download/3876| archive-url = https://web.archive.org/web/20250323050424/https://bibliography.maps.org/resources/download/3876 | archive-date = 23 March 2025 }}</ref><ref name="Hoffer1965">{{cite journal | vauthors = Hoffer A | title = D-Lysergic Acid Diethylamide (LSD): A Review of its Present Status | journal = Clin Pharmacol Ther | volume = 6 | issue = 2| pages = 183–255 | date = 1965 | pmid = 14288188 | doi = 10.1002/cpt196562183 | url = https://bibliography.maps.org/resources/download/2117| archive-url = https://web.archive.org/web/20250330030934/https://bibliography.maps.org/resources/download/2117 | archive-date = 30 March 2025 | url-access = subscription }}</ref><ref name="IsbellMinerLogan1959">{{cite journal | vauthors = Isbell H, Miner EJ, Logan CR | title = Relationships of psychotomimetic to anti-serotonin potencies of congeners of lysergic acid diethylamide (LSD-25) | journal = Psychopharmacologia | volume = 1 | issue = | pages = 20–28 | date = 1959 | pmid = 14405872 | doi = 10.1007/BF00408108 | url = https://bibliography.maps.org/resources/download/13773#page=4| archive-url = https://web.archive.org/web/20220407150042/https://bibliography.maps.org/resources/download/13773#page=4 | archive-date = 7 April 2022 | url-access = subscription }}</ref><ref name="Oberlender1989">{{cite web | vauthors = Oberlender RA | title=Stereoselective aspects of hallucinogenic drug action and drug discrimination studies of entactogens | publisher=Purdue University | website=Purdue e-Pubs | date=May 1989 | url=https://bitnest.netfirms.com/external/Theses/Oberlender1989#page=49 | quote=Table 2. Relative potency values for lysergic acid amides. [...]}}</ref><ref name="KumbarSankar1973" /><ref name="SankarKumbar1974" /> | ||
{{Sticky}} | {{Sticky}} | ||
| Line 33: | Line 33: | ||
|- | |- | ||
| [[1-Methyllysergic acid ethylamide]] || MLA-74 || ~2 || 0.05 || ? | | [[1-Methyllysergic acid ethylamide]] || MLA-74 || ~2 || 0.05 || ? | ||
|- | |- | ||
| [[Lysergic acid methylethylamide]] || LME-54 || ? || ~0.33 || ? | | [[Lysergic acid methylethylamide]] || LME-54 || ? || ~0.33 || ? | ||
| Line 45: | Line 43: | ||
|- | |- | ||
| [[9,10-Dihydro-LSD]] || 9,10-DH-LSD || >2.5 || <0.02 || ? | | [[9,10-Dihydro-LSD]] || 9,10-DH-LSD || >2.5 || <0.02 || ? | ||
|- | |||
| [[Lumi-LSD|10-Hydroxy-9,10-dihydro-LSD]] || Lumi-LSD || ? || <0.01 || ? | |||
|- | |- | ||
| [[2-Bromo-LSD]] || BOL-148 || >1 (≥6–20) || <0.1 (≤0.005–0.02) || ? | | [[2-Bromo-LSD]] || BOL-148 || >1 (≥6–20) || <0.1 (≤0.005–0.02) || ? | ||
| Line 50: | Line 50: | ||
| [[2-Iodo-LSD]] || IOL || ? || ? || ? | | [[2-Iodo-LSD]] || IOL || ? || ? || ? | ||
|- | |- | ||
| [[2- | | [[2-Oxo-LSD]] (2-oxy-LSD) || – || >0.3 || ? || ? | ||
|- | |- | ||
| [[1-Acetyl-LSD]] || ALD-52 || 0.1–0.2 || 1 || ? | | [[1-Acetyl-LSD]] || ALD-52 || 0.1–0.2 || 1 || ? | ||
| Line 58: | Line 58: | ||
| [[1-Hydroxymethyl-LSD]] || OML-632 || ? || ~0.7 || ? | | [[1-Hydroxymethyl-LSD]] || OML-632 || ? || ~0.7 || ? | ||
|- | |- | ||
| [[1-Methyl-2-bromo-LSD]] || MBL-61 || >10 || <0.01 || ? | | [[1-Methyl-2-bromo-LSD]] || MBL-61, MOB-61 || >10 || <0.01 || ? | ||
|- | |- | ||
| [[1-Methyl-2-iodo-LSD]] || MIL || ? || ? || ? | | [[1-Methyl-2-iodo-LSD]] || MIL || ? || ? || ? | ||
| Line 64: | Line 64: | ||
| [[Lysergic acid propylamide]] || LAP || >0.5 || <0.2 || ? | | [[Lysergic acid propylamide]] || LAP || >0.5 || <0.2 || ? | ||
|- | |- | ||
| [[Lysergic acid methylpropylamide]] || LMP || >0.1 || <1 || ? | | [[Lysergic acid methylpropylamide]] || LMP-55, LAMPA || >0.1 || <1 || ? | ||
|- | |- | ||
| [[Lysergic acid ethylpropylamide]] || LEP-57 || ? || ~0.33 || ? | | [[Lysergic acid ethylpropylamide]] || LEP-57 || ? || ~0.33 || ? | ||
| Line 104: | Line 104: | ||
| [[6-Propynyl-nor-LSD]] || PARGY-LAD || 0.16–0.5 || 0.2–0.6 || ? | | [[6-Propynyl-nor-LSD]] || PARGY-LAD || 0.16–0.5 || 0.2–0.6 || ? | ||
|- | |- | ||
| [[6-(β-Phenethyl)-nor-LSD]] || | | [[6-(β-Phenethyl)-nor-LSD]] || PHENETH-LAD || >0.35–0.5 || <0.3 || ? | ||
|- class="sortbottom" | |- class="sortbottom" | ||
| colspan="5" style="width: 1px; background-color:#eaecf0; text-align: center;" | '''Footnotes:''' <sup>a</sup> = Ergonovine is lysergic acid hydroxyisopropylamide. <sup>b</sup> = Methylergonovine is lysergic acid hydroxy-''sec''-butylamide. <sup>c</sup> = Methysergide is 1-methylmethylergonovine (1-methyllysergic acid hydroxy-''sec''-butylamide). '''Refs:''' ''Main:'' <ref name="Shulgin2003" /><ref name="JacobShulgin1994" /><ref name="Shulgin1982" /><ref name="Shulgin1980" /><ref name="TiHKAL1997" /><ref name="Abramson1959">{{cite journal | last=Abramson | first=H. A. | title=Lysergic Acid Diethylamide (LSD-25): XXIX. The Response Index as a Measure of Threshold Activity of Psychotropic Drugs in Man | journal=The Journal of Psychology | volume=48 | issue=1 | date=1959 | issn=0022-3980 | doi=10.1080/00223980.1959.9916341 | pages=65–78 | url=https://bibliography.maps.org/resources/download/20361| archive-url=https://web.archive.org/web/20250330025251/https://bibliography.maps.org/resources/download/20361 | archive-date=30 March 2025 | url-access=subscription }}</ref><ref name="HalberstadtChathaKlein2020">{{cite journal | vauthors = Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD | title = Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species | journal = Neuropharmacology | volume = 167 | issue = | pages = 107933 | date = May 2020 | pmid = 31917152 | pmc = 9191653 | doi = 10.1016/j.neuropharm.2019.107933 | url = http://usdbiology.com/cliff/Courses/Advanced%20Seminars%20in%20Neuroendocrinology/Serotonergic%20Psychedelics%2020/Halberstadt%2020%20Neuropharm%20potency%20of%20hallucinogens%20%20head-twitch.pdf | quote = Table 4 Human potency data for selected hallucinogens. [...] }}</ref><ref name="TittarelliMannocchiPantano2015">{{cite journal | vauthors = Tittarelli R, Mannocchi G, Pantano F, Romolo FS | title = Recreational use, analysis and toxicity of tryptamines | journal = Curr Neuropharmacol | volume = 13 | issue = 1 | pages = 26–46 | date = January 2015 | pmid = 26074742 | doi = 10.2174/1570159X13666141210222409 | pmc = 4462041 | url = https://web.archive.org/web/20250403082210/https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=90639cbd4ed3fc89df491868f3276f2288f9b1d2 | quote = Ergine, or lysergic acid amide (LSA), is an alkaloid of the ergoline family closely related to LSD, found in the seeds of Argyreia nervosa (Hawaiian baby woodrose) and Ipomoea violacea (Morning Glories). Hallucinogenic activity of LSA occurs with 4-10 seeds of Argyreia nervosa or with 150–200 seeds (3–6 g) of Ipomoea violacea: seeds could be crushed or eaten whole, or also drunk as an extract, after soaking in water [42]. The onset of the hallucinatory effects, after ingestion of Hawaiian Baby Woodrose, is from 20 to 40 minutes and their total duration is from 5 to 8 hours: the plateau is reached after 4-6 hours and the return to normality is after 1-2 hours from the plateau. [...] However, as regards to the assumption of the Morning Glory seeds, the onset of the hallucinatory effects is from 30 to 180 minutes and they last for 4 to 10 hours. The users reported that they return to normality after about 24 hours [67].}}</ref><ref name="KumbarSankar1973">{{cite journal | vauthors = Kumbar M, Sankar DV | title = Quantum chemical studies on drug actions. 3. Correlation of hallucinogenic and anti-serotonin activity of lysergic acid derivatives with quantum chemical data | journal = Res Commun Chem Pathol Pharmacol | volume = 6 | issue = 1 | pages = 65–100 | date = July 1973 | pmid = 4734018 | doi = | url = https://bibliography.maps.org/resources/download/14168 | archive-url = https://web.archive.org/web/20250329003102/https://bibliography.maps.org/resources/download/14168 | archive-date = 29 March 2025 | quote=Table I – Structure and Several Biological Activities of Lysergates [...]}}</ref><ref name="SankarKumbar1974">{{cite journal | vauthors = Sankar DV, Kumbar M | title = Quantum chemical studies on drug actions. IV. Correlation of substituent structures and anti-serotonin activity in lysergamide series | journal = Res Commun Chem Pathol Pharmacol | volume = 7 | issue = 2 | pages = 259–274 | date = February 1974 | pmid = 4818373 | doi = | quote = Table I – Quantum Chemical Data on Lysergamide Derivatives | url = https://bibliography.maps.org/resources/download/20652#page=7| archive-url = https://web.archive.org/web/20250329003312/https://bibliography.maps.org/resources/download/20652#page=7 | archive-date = 29 March 2025 }}</ref><ref name="BrimblecombePinder1975">{{cite book | vauthors = Brimblecombe RW, Pinder RM | chapter = Indolealkylamines and Related Compounds | pages = 98–144 | title = Hallucinogenic Agents | date = 1975 | publisher = Wright-Scientechnica | location = Bristol | isbn = 978-0-85608-011-1 | oclc = 2176880 | ol = OL4850660M | url = https://books.google.com/books?id=wU9tQgAACAAJ | chapter-url = https://bitnest.netfirms.com/external/Books/978-0-85608-011-1#page=55 | quote = Table 4.3.—Comparative Hallucinogenic Potencies in Man of Derivatives of D-Lysergic Acid. [...]}}</ref><ref name="Mangner1978" /><ref name="Fanchamps1978" /><ref name="IsbellMinerLogan1959" /><ref name="Hoffer1965" /><ref name="GuptaSinghBindal1983">{{cite journal | last=Gupta | first=Satya P. | last2=Singh | first2=Prithvi | last3=Bindal | first3=Mahesh C. | title=QSAR studies on hallucinogens | journal=Chemical Reviews | volume=83 | issue=6 | date=1 December 1983 | issn=0009-2665 | doi=10.1021/cr00058a003 | pages=633–649 | url=https://pubs.acs.org/doi/abs/10.1021/cr00058a003 | quote= TABLE XII. Antiserotonin and Hallucinogenic Activities and Hückel's Total MO Energy of LSD and its Analogues [...] Data collected by Kumbar and Siva Sankar,91,92 from ref 70a, 87, 88, and 90; all activities are relative to that of LSD taken as 100.}}</ref> ''Additional:'' <ref name="ChenDeWitBos2020">{{cite report | last1=Chen | first1=W. | last2=De Wit-Bos | first2=L. | title=Risk assessment of Argyreia nervosa | date=2020 | doi=10.21945/rivm-2019-0210 | url=https://www.rivm.nl/bibliotheek/rapporten/2019-0210.pdf}}</ref><ref name="BigwoodOttThompson1979">{{cite journal | vauthors = Bigwood J, Ott J, Thompson C, Neely P | title = Entheogenic effects of ergonovine | journal = J Psychedelic Drugs | volume = 11 | issue = 1–2 | pages = 147–149 | date = 1979 | pmid = 522166 | doi = 10.1080/02791072.1979.10472099 | url = https://bibliography.maps.org/resources/download/12845 | archive-url = https://web.archive.org/web/20250328185507/https://bibliography.maps.org/resources/download/12845 | archive-date = 28 March 2025 | quote = In 1977 and 1978 Hofmann reported that ergonovine maleate was entheogenic,1 a surprising finding in view of its widespread use in obstetrics (Wasson, Hofmann & Ruck 1978; Hofmann 1977). This report was based on a self-experiment conducted by Hofmann on 1 April 1976, with 2.0 mg of ergonovine maleate taken orally. Hofmann reported that this dose manifested a "slightly hallucinogenic activity" lasting more than five hours.2 [...] Our experiments corroborate Hofmann's report that ergonovine possesses entheogenic properties. We found the active dose to lie between 5.0 and 10.0 mg, peroral. It is interesting to note that Hofmann experienced distinct entheogenic effects at 2.0 mg, while Wasson and Ruck did not. Similarly, J.B. experienced distinct entheogenic effects at 3.0 mg, whereas J.O. and P.N. did not. This underscores the importance of metabolic individuality in the uptake and metabolism of mind-altering drugs. With respect to entheogenic effects 10 mg of ergonovine maleate is roughly equivalent to 50 μg is, ergonovine possesses about that LSD-tartrate, 1/200th the entheogenic potency of LSD.| url-access = subscription }}</ref><ref name="GorodetzkyIsbell1964">{{cite journal | vauthors = Gorodetzky CW, Isbell H | title = A comparison of 2,3-dihydro-lysergic acid diethylamide with LSD-25 | journal = Psychopharmacologia | volume = 6 | issue = 3 | pages = 229–233 | date = September 1964 | pmid = 5319153 | doi = 10.1007/BF00404013 | url = }}</ref> | | colspan="5" style="width: 1px; background-color:#eaecf0; text-align: center;" | '''Footnotes:''' <sup>a</sup> = [[Ergonovine]] is lysergic acid hydroxyisopropylamide. <sup>b</sup> = [[Methylergonovine]] is lysergic acid hydroxy-''sec''-butylamide. <sup>c</sup> = [[Methysergide]] is 1-methylmethylergonovine (1-methyllysergic acid hydroxy-''sec''-butylamide). '''Refs:''' ''Main:'' <ref name="Shulgin2003" /><ref name="JacobShulgin1994" /><ref name="Shulgin1982" /><ref name="Shulgin1980" /><ref name="TiHKAL1997" /><ref name="Abramson1959">{{cite journal | last=Abramson | first=H. A. | title=Lysergic Acid Diethylamide (LSD-25): XXIX. The Response Index as a Measure of Threshold Activity of Psychotropic Drugs in Man | journal=The Journal of Psychology | volume=48 | issue=1 | date=1959 | issn=0022-3980 | doi=10.1080/00223980.1959.9916341 | pages=65–78 | url=https://bibliography.maps.org/resources/download/20361| archive-url=https://web.archive.org/web/20250330025251/https://bibliography.maps.org/resources/download/20361 | archive-date=30 March 2025 | url-access=subscription }}</ref><ref name="HalberstadtChathaKlein2020">{{cite journal | vauthors = Halberstadt AL, Chatha M, Klein AK, Wallach J, Brandt SD | title = Correlation between the potency of hallucinogens in the mouse head-twitch response assay and their behavioral and subjective effects in other species | journal = Neuropharmacology | volume = 167 | issue = | pages = 107933 | date = May 2020 | pmid = 31917152 | pmc = 9191653 | doi = 10.1016/j.neuropharm.2019.107933 | url = http://usdbiology.com/cliff/Courses/Advanced%20Seminars%20in%20Neuroendocrinology/Serotonergic%20Psychedelics%2020/Halberstadt%2020%20Neuropharm%20potency%20of%20hallucinogens%20%20head-twitch.pdf | quote = Table 4 Human potency data for selected hallucinogens. [...] }}</ref><ref name="TittarelliMannocchiPantano2015">{{cite journal | vauthors = Tittarelli R, Mannocchi G, Pantano F, Romolo FS | title = Recreational use, analysis and toxicity of tryptamines | journal = Curr Neuropharmacol | volume = 13 | issue = 1 | pages = 26–46 | date = January 2015 | pmid = 26074742 | doi = 10.2174/1570159X13666141210222409 | pmc = 4462041 | url = https://web.archive.org/web/20250403082210/https://citeseerx.ist.psu.edu/document?repid=rep1&type=pdf&doi=90639cbd4ed3fc89df491868f3276f2288f9b1d2 | quote = Ergine, or lysergic acid amide (LSA), is an alkaloid of the ergoline family closely related to LSD, found in the seeds of Argyreia nervosa (Hawaiian baby woodrose) and Ipomoea violacea (Morning Glories). Hallucinogenic activity of LSA occurs with 4-10 seeds of Argyreia nervosa or with 150–200 seeds (3–6 g) of Ipomoea violacea: seeds could be crushed or eaten whole, or also drunk as an extract, after soaking in water [42]. The onset of the hallucinatory effects, after ingestion of Hawaiian Baby Woodrose, is from 20 to 40 minutes and their total duration is from 5 to 8 hours: the plateau is reached after 4-6 hours and the return to normality is after 1-2 hours from the plateau. [...] However, as regards to the assumption of the Morning Glory seeds, the onset of the hallucinatory effects is from 30 to 180 minutes and they last for 4 to 10 hours. The users reported that they return to normality after about 24 hours [67].}}</ref><ref name="KumbarSankar1973">{{cite journal | vauthors = Kumbar M, Sankar DV | title = Quantum chemical studies on drug actions. 3. Correlation of hallucinogenic and anti-serotonin activity of lysergic acid derivatives with quantum chemical data | journal = Res Commun Chem Pathol Pharmacol | volume = 6 | issue = 1 | pages = 65–100 | date = July 1973 | pmid = 4734018 | doi = | url = https://bibliography.maps.org/resources/download/14168 | archive-url = https://web.archive.org/web/20250329003102/https://bibliography.maps.org/resources/download/14168 | archive-date = 29 March 2025 | quote=Table I – Structure and Several Biological Activities of Lysergates [...]}}</ref><ref name="SankarKumbar1974">{{cite journal | vauthors = Sankar DV, Kumbar M | title = Quantum chemical studies on drug actions. IV. Correlation of substituent structures and anti-serotonin activity in lysergamide series | journal = Res Commun Chem Pathol Pharmacol | volume = 7 | issue = 2 | pages = 259–274 | date = February 1974 | pmid = 4818373 | doi = | quote = Table I – Quantum Chemical Data on Lysergamide Derivatives | url = https://bibliography.maps.org/resources/download/20652#page=7| archive-url = https://web.archive.org/web/20250329003312/https://bibliography.maps.org/resources/download/20652#page=7 | archive-date = 29 March 2025 }}</ref><ref name="BrimblecombePinder1975">{{cite book | vauthors = Brimblecombe RW, Pinder RM | chapter = Indolealkylamines and Related Compounds | pages = 98–144 | title = Hallucinogenic Agents | date = 1975 | publisher = Wright-Scientechnica | location = Bristol | isbn = 978-0-85608-011-1 | oclc = 2176880 | ol = OL4850660M | url = https://books.google.com/books?id=wU9tQgAACAAJ | chapter-url = https://bitnest.netfirms.com/external/Books/978-0-85608-011-1#page=55 | quote = Table 4.3.—Comparative Hallucinogenic Potencies in Man of Derivatives of D-Lysergic Acid. [...]}}</ref><ref name="Mangner1978" /><ref name="Fanchamps1978" /><ref name="IsbellMinerLogan1959" /><ref name="Hoffer1965" /><ref name="GuptaSinghBindal1983">{{cite journal | last=Gupta | first=Satya P. | last2=Singh | first2=Prithvi | last3=Bindal | first3=Mahesh C. | title=QSAR studies on hallucinogens | journal=Chemical Reviews | volume=83 | issue=6 | date=1 December 1983 | issn=0009-2665 | doi=10.1021/cr00058a003 | pages=633–649 | url=https://pubs.acs.org/doi/abs/10.1021/cr00058a003 | quote= TABLE XII. Antiserotonin and Hallucinogenic Activities and Hückel's Total MO Energy of LSD and its Analogues [...] Data collected by Kumbar and Siva Sankar,91,92 from ref 70a, 87, 88, and 90; all activities are relative to that of LSD taken as 100.}}</ref> ''Additional:'' <ref name="ChenDeWitBos2020">{{cite report | last1=Chen | first1=W. | last2=De Wit-Bos | first2=L. | title=Risk assessment of Argyreia nervosa | date=2020 | doi=10.21945/rivm-2019-0210 | url=https://www.rivm.nl/bibliotheek/rapporten/2019-0210.pdf}}</ref><ref name="BigwoodOttThompson1979">{{cite journal | vauthors = Bigwood J, Ott J, Thompson C, Neely P | title = Entheogenic effects of ergonovine | journal = J Psychedelic Drugs | volume = 11 | issue = 1–2 | pages = 147–149 | date = 1979 | pmid = 522166 | doi = 10.1080/02791072.1979.10472099 | url = https://bibliography.maps.org/resources/download/12845 | archive-url = https://web.archive.org/web/20250328185507/https://bibliography.maps.org/resources/download/12845 | archive-date = 28 March 2025 | quote = In 1977 and 1978 Hofmann reported that ergonovine maleate was entheogenic,1 a surprising finding in view of its widespread use in obstetrics (Wasson, Hofmann & Ruck 1978; Hofmann 1977). This report was based on a self-experiment conducted by Hofmann on 1 April 1976, with 2.0 mg of ergonovine maleate taken orally. Hofmann reported that this dose manifested a "slightly hallucinogenic activity" lasting more than five hours.2 [...] Our experiments corroborate Hofmann's report that ergonovine possesses entheogenic properties. We found the active dose to lie between 5.0 and 10.0 mg, peroral. It is interesting to note that Hofmann experienced distinct entheogenic effects at 2.0 mg, while Wasson and Ruck did not. Similarly, J.B. experienced distinct entheogenic effects at 3.0 mg, whereas J.O. and P.N. did not. This underscores the importance of metabolic individuality in the uptake and metabolism of mind-altering drugs. With respect to entheogenic effects 10 mg of ergonovine maleate is roughly equivalent to 50 μg is, ergonovine possesses about that LSD-tartrate, 1/200th the entheogenic potency of LSD.| url-access = subscription }}</ref><ref name="GorodetzkyIsbell1964">{{cite journal | vauthors = Gorodetzky CW, Isbell H | title = A comparison of 2,3-dihydro-lysergic acid diethylamide with LSD-25 | journal = Psychopharmacologia | volume = 6 | issue = 3 | pages = 229–233 | date = September 1964 | pmid = 5319153 | doi = 10.1007/BF00404013 | url = }}</ref> | ||
|} | |} | ||
The properties of various additional lysergamides, for instance in terms of [[serotonin antagonism]], have also been described.<ref name="Cerletti1958">{{cite journal | vauthors = Cerletti A, Doepfner W | title = Comparative study on the serotonin antagonism of amide derivatives of lysergic acid and of ergot alkaloids | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 122 | issue = 1 | pages = 124–136 | date = January 1958 | pmid = 13502837 | doi = 10.1016/S0022-3565(25)11933-2 | url = https://web.archive.org/web/20250630233202/https://bibliography.maps.org/resources/download/19096}}</ref> | |||
==History== | ==History== | ||
Many [[synthetic compound|synthetic]] lysergamide [[structural analog|analogue]]s of LSD were first described by | Lysergamides, such as [[ergine]], [[isoergine]], and [[ergometrine]], were discovered by the early 1930s,<ref name="BrimblecombePinder1975" /><ref name="Rav2011">{{cite book| vauthors = Ravina E |title=The evolution of drug discovery : from traditional medicines to modern drugs|date=2011|publisher=Wiley-VCH|location=Weinheim|isbn=9783527326693|page=245|edition= 1st |url=https://books.google.com/books?id=iDNy0XxGqT8C&pg=PA245|url-status=live|archive-url=https://web.archive.org/web/20151226162800/https://books.google.ca/books?id=iDNy0XxGqT8C&pg=PA245|archive-date=2015-12-26}}</ref><ref name="SmithTimmis1932">{{cite journal | vauthors = Smith S, Timmis GM |date=1932 |title=98. The alkaloids of ergot. Part III. Ergine, a new base obtained by the degradation of ergotoxine and ergotinine |url=https://xlink.rsc.org/?DOI=jr9320000763 |journal=Journal of the Chemical Society (Resumed) |language=en |pages=763–766 |doi=10.1039/jr9320000763 |issn=0368-1769|url-access=subscription }}</ref> and LSD was discovered by 1938 and its hallucinogenic effects in 1943 by [[Albert Hofmann]].<ref name="WalkerPullellaPiggott2023">{{cite journal | last1=Walker | first1=Scott R. | last2=Pullella | first2=Glenn A. | last3=Piggott | first3=Matthew J. | last4=Duggan | first4=Peter J. | title=Introduction to the chemistry and pharmacology of psychedelic drugs | journal=Australian Journal of Chemistry | volume=76 | issue=5 | date=5 July 2023 | issn=0004-9425 | doi=10.1071/CH23050 | doi-access=free | pages=236–257 | url=https://www.publish.csiro.au/ch/pdf/CH23050 | access-date=4 April 2025}}</ref><ref name="McKenna1999">{{cite book | last=McKenna | first=Terence | chapter=[Chapter 14:] A Brief History of Psychedelics | pages=223–245 | title=Food of the Gods: The Search for the Original Tree of Knowledge : a Radical History of Plants, Drugs and Human Evolution | publisher=Rider | date=1999 | isbn=978-0-7126-7038-8 | url=https://alquimiahealingarts.com/wp-content/uploads/2020/03/Food-Of-The-Gods-Terence-Mckenna.pdf#page=117}}</ref> Many [[synthetic compound|synthetic]] lysergamide [[structural analog|analogue]]s of LSD, modified at the [[amide]] and/or 1 or 2 positions, were first described by Hofmann and colleagues in the mid-to-late 1950s.<ref name="Hofmann1959" /><ref name="Rothlin1957" /><ref name="Abramson1959" /> | ||
<ref name="StollHofmann1955">{{cite journal | last=Stoll | first=A. | last2=Hofmann | first2=A. | title=Amide der stereoisomeren Lysergsäuren und Dihydro‐lysergsäuren. 38. Mitteilung über Mutterkornalkaloide | trans-title=Amides of stereoisomeric lysergic and dihydrolysergic acids. 38. Ergot alkaloids | journal=Helvetica Chimica Acta | volume=38 | issue=2 | date=1955 | issn=0018-019X | doi=10.1002/hlca.19550380207 | pages=421–433 | url=https://onlinelibrary.wiley.com/doi/10.1002/hlca.19550380207 | access-date=5 June 2025}}</ref> ''N''(6)-Substituted lysergamides were first reported in 1970 and thereafter in the 1970s and 1980s by multiple groups, including Hofmann and colleagues, Yuji Nakahara and Tetsukichi Niwaguchi and colleagues, and [[David E. Nichols]] and colleagues.<ref name="NicholsOberlenderMcKenna1991">{{cite book | vauthors=Nichols DE, Oberlender R, McKenna DJ | chapter=Stereochemical Aspects of Hallucinogenesis | veditors=Watson RR | title=Biochemistry and Physiology of Substance Abuse | volume=3 | publisher=CRC Press | publication-place=Boca Raton, Fla. | year=1991 | isbn=978-0-8493-4463-3 | oclc=26748320 | pages=1–39 | url=https://archive.org/details/biochemistryphys0003unse/ | chapter-url=https://bitnest.netfirms.com/external/Books/BiochemistryPhysiologySubstanceAbuse3.1 | quote=Chemical transformations at N(6) were not accomplished until after clinical studies had been terminated. Initial work in this area was reported in 1970 by Fehr et al.184 who synthesized d-lysergic acid with various N(6) alkyl groups from 6-nor-d-lysergic acid methyl ester.151 Similar chemistry was first applied to LSD by Nakahara and Niwaguchi,185 then by Niwaguchi et al.,186 and most recently by Hoffman and Nichols.162 Initial pharmacological studies identified high activity in the isolated rat uterus preparation for the ethyl, propyl, and allyl analogues, from which high potency in the CNS was predicted.161}}</ref><ref name="FehrStadlerHofmann1970">{{cite journal | last=Fehr | first=T. | last2=Stadler | first2=P. A. | last3=Hofmann | first3=A. | title=Demethylierung des Lysergsäuregerüstes. 73. Mitteilung über Mutterkornalkaloide [1] | journal=Helvetica Chimica Acta | volume=53 | issue=8 | date=1970 | issn=0018-019X | doi=10.1002/hlca.19700530832 | pages=2197–2201 | url=https://onlinelibrary.wiley.com/doi/10.1002/hlca.19700530832 | access-date=29 June 2025}}</ref><ref name="NiwaguchiNakaharaIshii1976">{{cite journal | vauthors = Niwaguchi T, Nakahara Y, Ishii H | title=Lysergic Acid Diethylamideおよび関連化合物に関する研究(第4報)Norlysergic Acidの各種Amide誘導体ならびに関連化合物の合成 | trans-title=Studies on Lysergic Acid Diethylamide and Related Compounds. IV. Syntheses of Various Amide Derivatives of Norlysergic Acid and Related Compounds | journal=Yakugaku Zasshi | volume=96 | issue=5 | date=1976 | issn=0031-6903 | doi=10.1248/yakushi1947.96.5_673 | doi-access=free | pages=673–678 | pmid=987200 | url=https://www.jstage.jst.go.jp/article/yakushi1947/96/5/96_5_673/_pdf | access-date=27 March 2025}}</ref><ref name="HoffmanNichols1985" /> The psychedelic effects of ''N''(6)-substituted lysergamides were reported by [[Alexander Shulgin]] in 1986 and thereafter.<ref name="Nichols1986">{{cite journal | vauthors = Nichols DE | title = Studies of the Relationship Between Molecular Structure and Hallucinogenic Activity | journal = Pharmacol Biochem Behav | volume = 24 | issue = 2 | pages = 335–340 | date = February 1986 | pmid = 3952123 | doi = 10.1016/0091-3057(86)90362-x | url = https://bitnest.netfirms.com/external/10.1016/0091-3057(86)90362-X | quote = The ergolines can be viewed as rigid tetracyclic tryptamines. Within this class of compound is found the semisynthetic d-lysergic acid diethylamide (Fig 8) (d-LSD), the most potent of the hallucinogenic drugs. [...] Of the many structural modifications which have been made to the LSD structure, none had yielded a compound more potent than LSD itself. This report will briefly describe some derivatives of LSD which do appear to have somewhat higher potency than LSD. [...] The observations of potency comparable to, or greater than LSD [with N(6)-alkyl-substituted lysergamides] was of great interest. It seemed likely, based on the generalization in the drug discrimination assay and the high potencies of several of the derivatives, that these might well be more potent hallucinogens in man than LSD. Very recently, preliminary studies were carried out (A T Shulgin, personal communication) which indicated that indeed, the N(6)-ethyl and the N(6)-allyl-nor-LSD derivatives are somewhat more potent than LSD, by perhaps a factor of 2–3. Early results also indicated that N(6)-propyl-nor-LSD retains activity comparable to LSD, but with perhaps less visual distortion. These preliminary results were obtained after only a few experiments with each compound and further evaluation to define the potency and character of these lysergamides is underway.| url-access = subscription }}</ref><ref name="Oberlender1989" /><ref name="JacobShulgin1994" /><ref name="TiHKAL1997" /> Additional novel lysergamides modified at the amide, like [[LA-3Cl-SB]] and [[LA-Aziridine]], were described by Nichols and [[Robert Oberlender]] and colleagues in the late 1980s,<ref name="PfaffHuangMarona-Lewicka1994">{{cite journal | vauthors = Pfaff RC, Huang X, Marona-Lewicka D, Oberlender R, Nichols DE | title = Lysergamides revisited | journal = NIDA Research Monograph | volume = 146 | pages = 52–73 | date = 1994 | pmid = 8742794 | url = https://bitnest.netfirms.com/external/Books/NIDA146.52 }}</ref><ref name="Oberlender1989" /><ref name="NicholsOberlenderMcKenna1991" /> while [[LSZ (drug)|LSZ]] was described by the same group in 2002.<ref name="NicholsFrescasMarona-Lewicka2002" /> | |||
==List of lysergamides== | ==List of lysergamides== | ||
| Line 122: | Line 125: | ||
|- | |- | ||
| [[File:Isoergine.svg|125px]] || [[Isoergine]] (isolysergic acid amide, isolysergamide) || 2889-26-1 || H || CH<sub>3</sub> || H || H || 8-[[epimer|epi]] | | [[File:Isoergine.svg|125px]] || [[Isoergine]] (isolysergic acid amide, isolysergamide) || 2889-26-1 || H || CH<sub>3</sub> || H || H || 8-[[epimer|epi]] | ||
|- | |||
| [[File:LA-methylamide_structure.png|125px]] || [[Lysergic acid methylamide|LAM]] (lysergic acid methylamide) || 50485-06-8 || H || CH<sub>3</sub> || CH<sub>3</sub> || H || - | |||
|- | |- | ||
| [[File:DAM-57.svg|125px]] || [[DAM-57]] (lysergic acid dimethylamide) || 4238-84-0 || H || CH<sub>3</sub> || CH<sub>3</sub> || CH<sub>3</sub> || - | | [[File:DAM-57.svg|125px]] || [[DAM-57]] (lysergic acid dimethylamide) || 4238-84-0 || H || CH<sub>3</sub> || CH<sub>3</sub> || CH<sub>3</sub> || - | ||
| Line 142: | Line 147: | ||
|- | |- | ||
| [[File:LAE-32.svg|125px]] || [[LAE-32]] (lysergic acid ethylamide) || 478-99-9 || H || CH<sub>3</sub> || [[Ethyl group|CH<sub>2</sub>CH<sub>3</sub>]] || H || - | | [[File:LAE-32.svg|125px]] || [[LAE-32]] (lysergic acid ethylamide) || 478-99-9 || H || CH<sub>3</sub> || [[Ethyl group|CH<sub>2</sub>CH<sub>3</sub>]] || H || - | ||
|- | |||
| [[File:LA-propylamide_structure.png|125px]] || [[Lysergic acid propylamide|LAP]] (lysergic acid propylamide) || ? || H || CH<sub>3</sub> || CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> || H || - | |||
|- | |- | ||
| [[File:LAiP_structure.png|125px]] || LAiP (lysergic acid isopropylamide) || || H || CH<sub>3</sub> || CH(CH<sub>3</sub>)<sub>2</sub> || H || - | | [[File:LAiP_structure.png|125px]] || LAiP (lysergic acid isopropylamide) || || H || CH<sub>3</sub> || CH(CH<sub>3</sub>)<sub>2</sub> || H || - | ||
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|- | |- | ||
| [[File:Lysergic acid dipropylamide.svg|125px]] || [[Dipropyllysergamide|DPL]] (lysergic acid dipropylamide) || || H || CH<sub>3</sub> || [[Propyl|CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>]] || [[Propyl|CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>]] || - | | [[File:Lysergic acid dipropylamide.svg|125px]] || [[Dipropyllysergamide|DPL]] (lysergic acid dipropylamide) || || H || CH<sub>3</sub> || [[Propyl|CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>]] || [[Propyl|CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>]] || - | ||
|- | |||
| [[File:LA-dibutylamide_structure.png|125px]] || [[LBB-66]] (lysergic acid dibutylamide) || || H || CH<sub>3</sub> || [[Butyl|CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>]] || [[Butyl|CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>]] || - | |||
|- | |- | ||
| [[File:DALAD.svg|125px]] || [[Diallyllysergamide|DAL]] (lysergic acid diallylamide) || || H || CH<sub>3</sub> || [[Allyl|H<sub>2</sub>C=CH-CH<sub>2</sub>]] || Allyl|H<sub>2</sub>C=CH-CH<sub>2</sub> || - | | [[File:DALAD.svg|125px]] || [[Diallyllysergamide|DAL]] (lysergic acid diallylamide) || || H || CH<sub>3</sub> || [[Allyl|H<sub>2</sub>C=CH-CH<sub>2</sub>]] || Allyl|H<sub>2</sub>C=CH-CH<sub>2</sub> || - | ||
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| [[File:LA-3Cl-SB_structure.png|125px]] || [[LA-3Cl-SB]] (lysergic acid ''N''-(3-chloro-''sec''-butyl)amide) || || H || CH<sub>3</sub> || CH(CH<sub>3</sub>)CClHCH<sub>3</sub> || H || - | | [[File:LA-3Cl-SB_structure.png|125px]] || [[LA-3Cl-SB]] (lysergic acid ''N''-(3-chloro-''sec''-butyl)amide) || || H || CH<sub>3</sub> || CH(CH<sub>3</sub>)CClHCH<sub>3</sub> || H || - | ||
|- | |- | ||
| [[File: | | [[File:LA-methylethylamide_structure.png|125px]] || [[LME-54]] (lysergic acid methylethylamide) || || H || CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>3</sub> || - | ||
|- | |- | ||
| [[File:EPLA_structure.png|125px]] || [[Ethylpropyllysergamide|EPLA]] (lysergic acid ethylpropylamide; LEP-57) || || H || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> || CH<sub>3</sub> || - | | [[File:MPLA_structure.png|125px]] || [[LAMPA]] (LMP-55; lysergic acid methylpropylamide) || 40158-98-3 || H || CH<sub>3</sub> || CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> || CH<sub>3</sub> || - | ||
|- | |||
| [[File:EPLA_structure.png|125px]] || [[Ethylpropyllysergamide|EPLA]] (lysergic acid ethylpropylamide; LEP-57) || || H || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub> || CH<sub>3</sub> || - | |||
|- | |- | ||
| [[File:LSD structural formulae v.1.png|125px]] || '''[[LSD]]''' (lysergic acid diethylamide; LAD) || 50-37-3 || H || CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || - | | [[File:LSD structural formulae v.1.png|125px]] || '''[[LSD]]''' (lysergic acid diethylamide; LAD) || 50-37-3 || H || CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || - | ||
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| [[File:ETH-LAD_structure.png|125px]] || [[ETH-LAD]] (6-ethyl-6-nor-LSD) || 65527-62-0 || H || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || - | | [[File:ETH-LAD_structure.png|125px]] || [[ETH-LAD]] (6-ethyl-6-nor-LSD) || 65527-62-0 || H || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || - | ||
|- | |- | ||
| [[File:PARGY-LAD.svg|125px]] || [[PARGY-LAD]] (6-propynyl-6-nor-LSD) || || H || [[Propynyl|HC≡C−CH<sub>2</sub>]] || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || - | | [[File:PARGY-LAD.svg|125px]] || [[PARGY-LAD]] (6-propynyl-6-nor-LSD) || 2767597-51-1 || H || [[Propynyl|HC≡C−CH<sub>2</sub>]] || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || - | ||
|- | |- | ||
| [[File:AL-LAD structure.svg|125px]] || [[AL-LAD]] (6-allyl-6-nor-LSD) || 65527-61-9 || H || H<sub>2</sub>C=CH-CH<sub>2</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || - | | [[File:AL-LAD structure.svg|125px]] || [[AL-LAD]] (6-allyl-6-nor-LSD) || 65527-61-9 || H || H<sub>2</sub>C=CH-CH<sub>2</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || - | ||
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| [[File:CYP-LAD.svg|125px]] || [[CYP-LAD]] (TRALA-22; 6-cyclopropyl-6-nor-LSD) || || H || [[Cyclopropyl|C<sub>3</sub>H<sub>5</sub>]] || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || - | | [[File:CYP-LAD.svg|125px]] || [[CYP-LAD]] (TRALA-22; 6-cyclopropyl-6-nor-LSD) || || H || [[Cyclopropyl|C<sub>3</sub>H<sub>5</sub>]] || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || - | ||
|- | |- | ||
| [[File:WO22-226408-13_structure.png|125px]] || CPM-LAD ( | | [[File:WO22-226408-13_structure.png|125px]] || [[CPM-LAD]] (6-cyclopropylmethyl-6-nor-LSD) || || H || CH<sub>2</sub>C<sub>3</sub>H<sub>5</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || - | ||
|- | |- | ||
| [[File:BU-LAD-2D-skeletal.svg|125px]] || [[BU-LAD]] (6-butyl-6-nor-LSD) || 96930-87-9 || H || [[Butyl|CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>]] || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || - | | [[File:BU-LAD-2D-skeletal.svg|125px]] || [[BU-LAD]] (6-butyl-6-nor-LSD) || 96930-87-9 || H || [[Butyl|CH<sub>2</sub>CH<sub>2</sub>CH<sub>2</sub>CH<sub>3</sub>]] || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || - | ||
|- | |- | ||
| [[File:PHENETHY-LAD_structure.png|150px]] || | | [[File:PHENETHY-LAD_structure.png|150px]] || [[PHENETH-LAD]] (6-(phenethyl)-6-nor-LSD) || || H || CH<sub>2</sub>CH<sub>2</sub>C<sub>6</sub>H<sub>5</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || - | ||
|- | |- | ||
| [[File:WO22-226408-10_structure.png|150px]] || [[NBOMe-LAD]] ( | | [[File:WO22-226408-10_structure.png|150px]] || [[NBOMe-LAD]] (6-(2-methoxybenzyl)-LAD) || || H || CH<sub>2</sub>C<sub>6</sub>H<sub>4</sub>-''o''-OCH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || - | ||
|- | |- | ||
| [[File:FLUOROETH-LAD_structure.png|125px]] || [[FLUORETH-LAD]] (FE-LAD; TRALA-15; 6-(2-fluoroethyl)-6-nor-LSD) || || H || CH<sub>2</sub>CH<sub>2</sub>F || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || - | | [[File:FLUOROETH-LAD_structure.png|125px]] || [[FLUORETH-LAD]] (FE-LAD; TRALA-15; 6-(2-fluoroethyl)-6-nor-LSD) || || H || CH<sub>2</sub>CH<sub>2</sub>F || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || - | ||
| Line 243: | Line 254: | ||
| [[File:1P-ETH-LAD Structural Formulae V2.svg|125px]] || [[1P-ETH-LAD]] (1-propionyl-6-ethyl-6-nor-LSD) || || COCH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || - | | [[File:1P-ETH-LAD Structural Formulae V2.svg|125px]] || [[1P-ETH-LAD]] (1-propionyl-6-ethyl-6-nor-LSD) || || COCH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || - | ||
|- | |- | ||
| [[File:1P-MIPLA_structure.png|125px]] || 1P-MIPLA (1-propionyl-lysergic acid methylisopropylamide) || || COCH<sub>2</sub>CH<sub>3</sub> || CH<sub>3</sub> || [[Isopropyl|CH(CH<sub>3</sub>)<sub>2</sub>]] || CH<sub>3</sub> || - | | [[File:1P-MIPLA_structure.png|125px]] || [[1P-MIPLA]] (1-propionyl-lysergic acid methylisopropylamide) || || COCH<sub>2</sub>CH<sub>3</sub> || CH<sub>3</sub> || [[Isopropyl|CH(CH<sub>3</sub>)<sub>2</sub>]] || CH<sub>3</sub> || - | ||
|- | |- | ||
| [[File:MLD-41.svg|125px]] || [[MLD-41]] (1-methyl-LSD) || 4238-85-1 || CH<sub>3</sub> || CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || - | | [[File:MLD-41.svg|125px]] || [[MLD-41]] (1-methyl-LSD) || 4238-85-1 || CH<sub>3</sub> || CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || - | ||
| Line 271: | Line 282: | ||
| [[File:2-bromo-LSD_structure.svg|125px]] || [[2-Bromo-LSD]] (BOL-148; bromolysergide) || 478-84-2 || H || CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || 2-Br | | [[File:2-bromo-LSD_structure.svg|125px]] || [[2-Bromo-LSD]] (BOL-148; bromolysergide) || 478-84-2 || H || CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || 2-Br | ||
|- | |- | ||
| [[File:1P-BOL-148_structure.png|125px]] || [[1P-BOL-148]] (1-propionyl-2-bromo-LSD) || || COCH<sub>2</sub>CH<sub>3</sub> || CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || 2-Br | | [[File:2-iodo-LSD_structure.png|125px]] || [[2-Iodo-LSD]] (IOL) || 3712-25-2 || H || CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || 2-I | ||
|- | |||
| [[File:2-oxo-LSD_structure.png|125px]] || [[2-Oxo-LSD]] (2-oxy-LSD) || ? || H || CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || 2-Oxo | |||
|- | |||
| [[File:3-OH-2-oxo-LSD_structure.png|125px]] || [[2-Oxo-3-hydroxy-LSD]] || ? || H || CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || 2-Oxo, 3-OH | |||
|- | |||
| [[File:1P-BOL-148_structure.png|125px]] || [[1P-BOL-148]] (1-propionyl-2-bromo-LSD) || || COCH<sub>2</sub>CH<sub>3</sub> || CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || 2-Br | |||
|- | |- | ||
| [[File:12-Hydroxy-LSD.svg|125px]] || [[12-Hydroxy-LSD]] (12-OH-LSD) || 60573-89-9 || H || CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || 12-OH | | [[File:12-Hydroxy-LSD.svg|125px]] || [[12-Hydroxy-LSD]] (12-OH-LSD) || 60573-89-9 || H || CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || 12-OH | ||
| Line 277: | Line 294: | ||
| [[File:12-MeO-LSD_structure.png|125px]] || [[12-Methoxy-LSD]] (12-MeO-LSD) || 50484-99-6 || H || CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || 12-OMe | | [[File:12-MeO-LSD_structure.png|125px]] || [[12-Methoxy-LSD]] (12-MeO-LSD) || 50484-99-6 || H || CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || 12-OMe | ||
|- | |- | ||
| [[File:13-F-LSD_structure.png|125px]] || 13-Fluoro-LSD<ref name="WO2021076572">{{cite patent | country = WO | number = 2021076572 | invent1 = [[David E. Olson]] | invent2 = Lee Dunlap | invent3 = Florence Wagner | invent4 = Milan Chytil, Noel Aaron Powell | status = | title = Ergoline-like compounds for promoting neural plasticity | pubdate = 22 April 2021 | gdate = | fdate = 14 October 2020 | pridate = 14 October 2020 | assign1 = [[Delix Therapeutics, Inc.]] | assign2 = [[The Regents of the University of California]] | url = https://patents.google.com/patent/WO2021076572/ | quote = [0124] In some embodiments, provided herein is a compound, or a pharmaceutically acceptable salt thereof, that is: [...]}}</ref> || || H || CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || 13-F | | [[File:13-F-LSD_structure.png|125px]] || 13-Fluoro-LSD<ref name="WO2021076572">{{cite patent | country = WO | number = 2021076572 | invent1 = [[David E. Olson]] | invent2 = Lee Dunlap | invent3 = Florence Wagner | invent4 = Milan Chytil, Noel Aaron Powell | status = | title = Ergoline-like compounds for promoting neural plasticity | pubdate = 22 April 2021 | gdate = | fdate = 14 October 2020 | pridate = 14 October 2020 | assign1 = [[Delix Therapeutics, Inc.]] | assign2 = [[The Regents of the University of California]] | url = https://patents.google.com/patent/WO2021076572/ | quote = [0124] In some embodiments, provided herein is a compound, or a pharmaceutically acceptable salt thereof, that is: [...]}}</ref> || || H || CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || 13-F | ||
|- | |||
| [[File:13-Hydroxy-LSD.svg|125px]] || [[13-Hydroxy-LSD]] || || H || CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || 13-OH | |||
|- | |- | ||
| [[File:13- | | [[File:13-MeO-LSD_structure.png|125px]] || [[13-Methoxy-LSD]] || || H || CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || 13-OMe | ||
|- | |- | ||
| [[File:14-HO-LSD_structure.png|125px]] || 14-Hydroxy-LSD | | [[File:14-HO-LSD_structure.png|125px]] || [[14-Hydroxy-LSD]] || || H || CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || 14-OH | ||
|- | |||
| [[File:14-MeO-LSD_structure.png|125px]] || [[14-Methoxy-LSD]] || || H || CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || CH<sub>2</sub>CH<sub>3</sub> || 14-OMe | |||
|} | |} | ||
| Line 292: | Line 313: | ||
! Structure !! Name !! Chemical name !! CAS # | ! Structure !! Name !! Chemical name !! CAS # | ||
|- | |- | ||
| [[File:2,3-Dihydro-LSD structure.png|125px]] || [[2,3-Dihydro-LSD]] (2,3-DH-LSD) || | | [[File:2,3-Dihydro-LSD structure.png|125px]] || [[2,3-Dihydro-LSD]] (2,3-DH-LSD) || ''N'',''N''-diethyl-6-methyl-9,10-didehydro-2,3-dihydroergoline-8β-carboxamide || ? | ||
|- | |- | ||
| [[File:9,10-Dihydro-LSD structure.png|125px]] || [[9,10-Dihydro-LSD]] (9,10-DH-LSD) || ( | | [[File:9,10-Dihydro-LSD structure.png|125px]] || [[9,10-Dihydro-LSD]] (9,10-DH-LSD) || (10ξ)-''N'',''N''-diethyl-6-methylergoline-8β-carboxamide || 3031-47-8 | ||
|- | |- | ||
| [[File:Bromerguride.png|125px]] || [[Bromerguride]] || 1,1-diethyl-3-(2-bromo-9,10-didehydro-6-methyl-8α-ergolinyl)urea || 83455-48-5 | | [[File:Bromerguride.png|125px]] || [[Bromerguride]] (2-bromolisuride) || 1,1-diethyl-3-(2-bromo-9,10-didehydro-6-methyl-8α-ergolinyl)urea || 83455-48-5 | ||
|- | |- | ||
| [[File:Descarboxylysergic acid.svg|100px]] || [[Descarboxylysergic acid]] || 6-methyl-9,10-didehydroergoline || 51867-17-5 | | [[File:Descarboxylysergic acid.svg|100px]] || [[Descarboxylysergic acid]] || 6-methyl-9,10-didehydroergoline || 51867-17-5 | ||
|- | |- | ||
| [[File:Disulergine_structure.png|125px]] || | | [[File:Disulergine_structure.png|125px]] || [[Disulergine]] || ''N'',''N''-dimethyl-''N''<nowiki>'</nowiki>-(6-methylergoline-8α-yl)sulfamide || 59032-40-5 | ||
|- | |- | ||
| [[File:Dosergoside_structure.png|175px]] || Dosergoside | | [[File:Dosergoside_structure.png|175px]] || [[Dosergoside]] || ''N''-((1''S'',2''R'',3''E'')-2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl)-6-methylergoline-8β-carboxamide || 87178-42-5 | ||
|- | |- | ||
| [[File:Ergoline Structural Formulae V.1.svg|125px]] || [[Ergoline]] || (6a''R'')-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-''fg'']quinoline | | [[File:Ergoline Structural Formulae V.1.svg|125px]] || [[Ergoline]] || (6a''R'')-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-''fg'']quinoline | ||
|| 478-88-6 | || 478-88-6 | ||
|- | |- | ||
| [[File:Etisulergine_structure.png|125px]] || Etisulergine | | [[File:Etisulergine_structure.png|125px]] || [[Etisulergine]] || ''N'',''N''-diethyl-''N''<nowiki>'</nowiki>-(6-methylergolin-8α-yl)sulfamide || 64795-23-9 | ||
|- | |- | ||
| [[File:GYKI-32887_structure.png|150px]] || | | [[File:GYKI-32887_structure.png|150px]] || [[GYKI-32887]] || 8-((''N''-2-azidoethyl-''N''-methylsulfonylamino)methyl)-6-methylergol-8-ene || 78463-86-2 | ||
|- | |- | ||
| [[File:JRT.svg|125px]] || [[JRT (drug)|JRT]] || (7''S'')-''N'',''N''-diethyl-6-methyl-6,9-diazatetracyclo[7.6.1.0<sup>2,7</sup>.0<sup>12,16</sup>]hexadeca-1(15),2,10,12(16),13-pentaene-4-carboxamide || ? | | [[File:JRT.svg|125px]] || [[JRT (drug)|JRT]] || (7''S'')-''N'',''N''-diethyl-6-methyl-6,9-diazatetracyclo[7.6.1.0<sup>2,7</sup>.0<sup>12,16</sup>]hexadeca-1(15),2,10,12(16),13-pentaene-4-carboxamide || ? | ||
|- | |||
| [[File:Lumi-LSD_structure.png|125px]] || [[Lumi-LSD]] (10-hydroxy-9,10-dihydro-LSD) || ''N'',''N''-diethyl-10-hydroxy-6-methylergoline-8β-carboxamide || | |||
|- | |- | ||
| [[File:Lysergine.svg|125px]] || [[Lysergine]] || 9,10-didehydro-6,8β-dimethylergoline || 519-10-8 | | [[File:Lysergine.svg|125px]] || [[Lysergine]] || 9,10-didehydro-6,8β-dimethylergoline || 519-10-8 | ||
| Line 319: | Line 342: | ||
| [[File:Lysergic acid chemical structure.svg|125px]] || [[Lysergic acid]] || 6-methyl-9,10-didehydroergoline-8β-carboxylic acid || 82-58-6 | | [[File:Lysergic acid chemical structure.svg|125px]] || [[Lysergic acid]] || 6-methyl-9,10-didehydroergoline-8β-carboxylic acid || 82-58-6 | ||
|- | |- | ||
| [[File:Lergotrile_structure.png|125px]] || [[Lergotrile]] || 2 | | [[File:Lergotrile_structure.png|125px]] || [[Lergotrile]] || 2-chloro-6-methylergoline-8β-acetonitrile || 36945-03-6 | ||
|- | |- | ||
| [[File:Lisuride.svg|125px]] || [[Lisuride]] || 1,1-diethyl-3-(6-methyl-9,10-didehydroergolin-8α-yl)urea || 18016-80-3 | | [[File:Lisuride.svg|125px]] || [[Lisuride]] || 1,1-diethyl-3-(6-methyl-9,10-didehydroergolin-8α-yl)urea || 18016-80-3 | ||
|- | |- | ||
| [[File:Proteguride_structure.png|125px]] || | | [[File:Proteguride_structure.png|125px]] || [[Proterguride]] (6-propyl-9,10-dihydrolisuride) || 1,1-diethyl-3-(6-n-propyl-8α-ergolinyl)urea || 77650-95-4 | ||
|- | |- | ||
| [[File:Terguride.png|125px]] || [[Terguride]] || ''N'',''N''-diethyl-''N''<nowiki>'</nowiki>-[(8α)-6-methylergolin-8-yl]urea || 37686-84-3 | | [[File:Terguride.png|125px]] || [[Terguride]] (9,10-dihydrolisuride) || ''N'',''N''-diethyl-''N''<nowiki>'</nowiki>-[(8α)-6-methylergolin-8-yl]urea || 37686-84-3 | ||
|- | |- | ||
|} | |} | ||
Latest revision as of 09:03, 1 July 2025
Template:Short description Template:Cs1 config
Lysergamides, also known as ergoamides[1][2] or as lysergic acid amides, are amides of lysergic acid (LA). They are ergolines, with some lysergamides being found naturally in ergot as well as other fungi. Lysergamides are notable in containing embedded phenethylamine and tryptamine moieties within their ergoline ring system.[3]
The simplest lysergamides are ergine (lysergic acid amide; LSA) and isoergine (iso-lysergic acid amide; iso-LSA). In terms of pharmacology, the lysergamides include numerous serotonin and dopamine receptor agonists, most notably the psychedelic drug lysergic acid diethylamide (LSD) but also a number of pharmaceutical drugs like ergometrine, methylergometrine, methysergide, and cabergoline.[4][5][6][7][8][9][10][11][12][13][14][15][16] Various analogues of LSD, such as the psychedelics ALD-52 (1A-LSD), ETH-LAD, LSZ, and 1P-LSD and the non-hallucinogenic 2-bromo-LSD (BOL-148), have also been developed. Ergopeptines like ergotamine, dihydroergotamine, and bromocriptine are also lysergamides, but with addition of a small peptide moiety at the amide. Close analogues of lysergamides that are not technically lysergamides themselves include lisuride, terguride, bromerguride, and JRT.
Lysergamides were first discovered and described in the 1930s.[17][18][19]
Simplified or partial ergolines and lysergamides, such as NDTDI (8,10-seco-LSD), DEMPDHPCA, and N-DEAOP-NMT, are also known.[20][21][22]
Use and effects
The dosages, potencies, durations, and effects of lysergamides have been reviewed by Alexander Shulgin.[23][24][25][26][27] They have also been reviewed by Albert Hofmann,[28] David E. Nichols,[29] and other researchers.[30][31][32][33][34][35][36][37][38]
| Common name | Code | Dose (mg) | Potency (×LSD) | Duration (h) |
|---|---|---|---|---|
| Lysergic acid amide (LSA; ergine) | LA-111 | 0.5–6 | ≤0.1 | ~4–10 |
| Isolysergic acid amide (iso-LSA; isoergine) | Iso-LA-819 | 2–5 | <0.1 | ~4–10 |
| Lysergic acid methylamide | LAM | ~0.5 | ≤0.2 | ? |
| Lysergic acid dimethylamide | DAM-57 | 0.5–1.2 | 0.1 | ? |
| Lysergic acid ethylamide | LAE-32 | 0.5–1.6 | ≤0.1 | ? |
| 1-Acetyllysergic acid ethylamide | ALA-10 | ~1.2 | ≤0.1 | ? |
| 1-Methyllysergic acid ethylamide | MLA-74 | ~2 | 0.05 | ? |
| Lysergic acid methylethylamide | LME-54 | ? | ~0.33 | ? |
| Lysergic acid diethylamide (LSD) | LSD-25, METH-LAD | 0.05–0.2 | 1 | 8–12 |
| Isolysergic acid diethylamide | Iso-LSD | >4 | <0.02 | ? |
| 2,3-Dihydro-LSD | 2,3-DH-LSD | ~0.15–0.4 | ~0.15 | ~8–12 |
| 9,10-Dihydro-LSD | 9,10-DH-LSD | >2.5 | <0.02 | ? |
| 10-Hydroxy-9,10-dihydro-LSD | Lumi-LSD | ? | <0.01 | ? |
| 2-Bromo-LSD | BOL-148 | >1 (≥6–20) | <0.1 (≤0.005–0.02) | ? |
| 2-Iodo-LSD | IOL | ? | ? | ? |
| 2-Oxo-LSD (2-oxy-LSD) | – | >0.3 | ? | ? |
| 1-Acetyl-LSD | ALD-52 | 0.1–0.2 | 1 | ? |
| 1-Methyl-LSD | MLD-41 | 0.2–0.3 | 0.3 | ? |
| 1-Hydroxymethyl-LSD | OML-632 | ? | ~0.7 | ? |
| 1-Methyl-2-bromo-LSD | MBL-61, MOB-61 | >10 | <0.01 | ? |
| 1-Methyl-2-iodo-LSD | MIL | ? | ? | ? |
| Lysergic acid propylamide | LAP | >0.5 | <0.2 | ? |
| Lysergic acid methylpropylamide | LMP-55, LAMPA | >0.1 | <1 | ? |
| Lysergic acid ethylpropylamide | LEP-57 | ? | ~0.33 | ? |
| Lysergic acid dipropylamide | DPL | >1 | <0.1 | ? |
| Lysergic acid dibutylamide | LBB-66 | ? | 0 | ? |
| Lysergic acid diallylamide | DAL | >1 | <0.1 | ? |
| Ergonovine (ergometrine)a | – | 5–10 | ≤0.01 | ? |
| Methylergonovine (methylergometrine)b | – | 2 | 0.05 | ? |
| Methysergidec | UML-491 | 4–8 | 0.02 | ? |
| Lysergic acid piperidide | LA-Pip | ? | ? | ? |
| Lysergic acid pyrrolidide | LPD-824 | ~0.8 | 0.05–0.1 | ? |
| Lysergic acid pyrrolinide | LPN | ? | ? | ? |
| 1-Methyllysergic acid pyrrolidide | MPD-75 | >1.6 | ≤0.1 | ? |
| Lysergic acid morpholide | LSM-775, SLM | 0.3–0.6 | 0.1–0.3 | ? |
| Lysergic acid 2,4-dimethylazetidide | LA-SS-Az, LSZ | 0.1–0.3 | 0.5 | ? |
| Nor-LSD (6-nor-LSD) | H-LAD | >0.5 | <0.2 | ? |
| 6-Ethyl-nor-LSD | ETH-LAD | 0.04–0.15 | 2 | 8–12 |
| 6-Propyl-nor-LSD | PRO-LAD | 0.08–0.2 | 1 | 6–8 |
| 6-Allyl-nor-LSD | AL-LAD, ALLY-LAD | 0.05–0.16 | 1 | 6–8 |
| 6-n-Butyl-nor-LSD | BU-LAD | ≥0.4–0.5 | <0.3 | ? |
| 6-Propynyl-nor-LSD | PARGY-LAD | 0.16–0.5 | 0.2–0.6 | ? |
| 6-(β-Phenethyl)-nor-LSD | PHENETH-LAD | >0.35–0.5 | <0.3 | ? |
| Footnotes: a = Ergonovine is lysergic acid hydroxyisopropylamide. b = Methylergonovine is lysergic acid hydroxy-sec-butylamide. c = Methysergide is 1-methylmethylergonovine (1-methyllysergic acid hydroxy-sec-butylamide). Refs: Main: [23][24][25][26][27][39][40][41][37][38][17][31][32][35][34][42] Additional: [43][44][45] | ||||
The properties of various additional lysergamides, for instance in terms of serotonin antagonism, have also been described.[46]
History
Lysergamides, such as ergine, isoergine, and ergometrine, were discovered by the early 1930s,[17][18][19] and LSD was discovered by 1938 and its hallucinogenic effects in 1943 by Albert Hofmann.[47][48] Many synthetic lysergamide analogues of LSD, modified at the amide and/or 1 or 2 positions, were first described by Hofmann and colleagues in the mid-to-late 1950s.[28][33][39] [49] N(6)-Substituted lysergamides were first reported in 1970 and thereafter in the 1970s and 1980s by multiple groups, including Hofmann and colleagues, Yuji Nakahara and Tetsukichi Niwaguchi and colleagues, and David E. Nichols and colleagues.[50][51][52][5] The psychedelic effects of N(6)-substituted lysergamides were reported by Alexander Shulgin in 1986 and thereafter.[53][36][24][27] Additional novel lysergamides modified at the amide, like LA-3Cl-SB and LA-Aziridine, were described by Nichols and Robert Oberlender and colleagues in the late 1980s,[54][36][50] while LSZ was described by the same group in 2002.[8]
List of lysergamides
| Structure | Name (synonyms) | CAS # | R1 | R6 | R2 | R3 | Other |
|---|---|---|---|---|---|---|---|
| File:Ergine.svg | Ergine (lysergic acid amide, lysergamide) | 478-94-4 | H | CH3 | H | H | - |
| File:Isoergine.svg | Isoergine (isolysergic acid amide, isolysergamide) | 2889-26-1 | H | CH3 | H | H | 8-epi |
| File:LA-methylamide structure.png | LAM (lysergic acid methylamide) | 50485-06-8 | H | CH3 | CH3 | H | - |
| File:DAM-57.svg | DAM-57 (lysergic acid dimethylamide) | 4238-84-0 | H | CH3 | CH3 | CH3 | - |
| File:Ergonovine-skeletal.svg | Ergometrine (ergonovine; lysergic acid propanolamide) | 60-79-7 | H | CH3 | CH(CH3)CH2OH | H | - |
| File:Propisergide.svg | Propisergide (1-methylergonovine) | 5793-04-4 | CH3 | CH3 | CH(CH3)CH2OH | H | - |
| File:Ergotamine-skeletal.svg | Ergotamine (an ergopeptine) | 113-15-5 | H | CH3 | -- | C17H18N2O4 | - |
| File:Methylergometrin.svg | Methylergometrine (methylergonovine; lysergic acid butanolamide) | 113-42-8 | H | CH3 | CH(CH2CH3)CH2OH | H | - |
| File:Methylsergide Structural Formula V1.svg | Methysergide (1-methyl-lysergic acid butanolamide) | 361-37-5 | CH3 | CH3 | CH(CH2CH3)CH2OH | H | - |
| File:Amesergide.svg | Amesergide (9,10-dihydro-11-isopropyllysergic acid cyclohexylamide) | 121588-75-8 | CH(CH3)2 | CH3 | C6H11 | H | - |
| File:LY-215840 structure.png | LY-215840 (1-isopropyl-9,10-dihydro-N-(2-hydroxycyclopent-anyl)lysergamide) | 137328-52-0 | CH(CH3)2 | CH3 | C5H8OH | H | - |
| File:Cabergoline.svg | Cabergoline (N-[3-(dimethylamino)propyl]-N-(ethylcarbamoyl)-6-(prop-2-en-1-yl)-9,10-dihydrolysergamide) | 81409-90-7 | H | H2C=CH-CH2 | CONHCH2CH3 | CH2CH2CH2N(CH3)2 | - |
| File:LAE-32.svg | LAE-32 (lysergic acid ethylamide) | 478-99-9 | H | CH3 | CH2CH3 | H | - |
| File:LA-propylamide structure.png | LAP (lysergic acid propylamide) | ? | H | CH3 | CH2CH2CH3 | H | - |
| File:LAiP structure.png | LAiP (lysergic acid isopropylamide) | H | CH3 | CH(CH3)2 | H | - | |
| File:LAtB structure.png | LAtB (lysergic acid tert-butylamide) | H | CH3 | C(CH3)3 | H | - | |
| File:LAcB structure.png | LAcB (lysergic acid cyclobutylamide) | H | CH3 | (CH2)4 | H | - | |
| File:LAcPe structure.png | Cepentil (lysergic acid cyclopentylamide) | H | CH3 | (CH2)5 | H | - | |
| File:SBULSD.svg | LSB (lysergic acid 2-butylamide) | 137765-82-3 | H | CH3 | CH(CH3)CH2CH3 | H | - |
| File:LS3P structure.png | LSP (lysergic acid 3-pentylamide) | H | CH3 | CH(CH2CH3)CH2CH3 | H | - | |
| File:Lysergic acid dipropylamide.svg | DPL (lysergic acid dipropylamide) | H | CH3 | CH2CH2CH3 | CH2CH2CH3 | - | |
| File:LA-dibutylamide structure.png | LBB-66 (lysergic acid dibutylamide) | H | CH3 | CH2CH2CH2CH3 | CH2CH2CH2CH3 | - | |
| File:DALAD.svg | DAL (lysergic acid diallylamide) | H | CH3 | H2C=CH-CH2 | H2C=CH-CH2 | - | |
| File:MIPLSD.svg | MIPLA (lysergic acid methylisopropylamide) | 100768-08-9 | H | CH3 | CH(CH3)2 | CH3 | - |
| File:EiPLA structure.png | EIPLA (lysergic acid ethylisopropylamide) | H | CH3 | CH(CH3)2 | CH2CH3 | - | |
| File:ECPLA structure.png | ECPLA (lysergic acid ethylcyclopropylamide) | H | CH3 | C3H5 | CH2CH3 | - | |
| File:Lysergic acid ethyl-2-hydroxyethylamide.svg | LEO (lysergic acid ethyl-2-hydroxyethylamide) | 65527-58-4 | H | CH3 | CH2CH2OH | CH2CH3 | - |
| File:LA-MeO structure.png | LA-MeO[55] | H | CH3 | CH2CH2OCH3 | CH2CH3 | - | |
| File:ETFELA.svg | ETFELA (lysergic acid N-ethyl-N-(2,2,2-trifluoroethyl)amide) | H | CH3 | CH2CF3 | CH2CH3 | - | |
| File:WO22-008627-4 structure.png | WO 2022/008627 Compound 4; TRALA-04[56] | H | CH3 | CH2CH2F | CH2CH3 | - | |
| File:WO22-226408-29 structure.png | WO 2022/226408 Example 29[57]; TRALA-08 | H | CH3 | CH2CH2F | CH2CH2F | - | |
| File:LA-3Cl-SB structure.png | LA-3Cl-SB (lysergic acid N-(3-chloro-sec-butyl)amide) | H | CH3 | CH(CH3)CClHCH3 | H | - | |
| File:LA-methylethylamide structure.png | LME-54 (lysergic acid methylethylamide) | H | CH3 | CH2CH3 | CH3 | - | |
| File:MPLA structure.png | LAMPA (LMP-55; lysergic acid methylpropylamide) | 40158-98-3 | H | CH3 | CH2CH2CH3 | CH3 | - |
| File:EPLA structure.png | EPLA (lysergic acid ethylpropylamide; LEP-57) | H | CH2CH3 | CH2CH2CH3 | CH3 | - | |
| File:LSD structural formulae v.1.png | LSD (lysergic acid diethylamide; LAD) | 50-37-3 | H | CH3 | CH2CH3 | CH2CH3 | - |
| File:Iso-LSD structure.png | Iso-LSD | 2126-78-5 | H | CH3 | CH2CH3 | CH2CH3 | 8-epi |
| File:Nor-LSD structure.png | Nor-LSD (6-nor-LSD) | 35779-43-2 | H | H | CH2CH3 | CH2CH3 | - |
| File:ETH-LAD structure.png | ETH-LAD (6-ethyl-6-nor-LSD) | 65527-62-0 | H | CH2CH3 | CH2CH3 | CH2CH3 | - |
| File:PARGY-LAD.svg | PARGY-LAD (6-propynyl-6-nor-LSD) | 2767597-51-1 | H | HC≡C−CH2 | CH2CH3 | CH2CH3 | - |
| File:AL-LAD structure.svg | AL-LAD (6-allyl-6-nor-LSD) | 65527-61-9 | H | H2C=CH-CH2 | CH2CH3 | CH2CH3 | - |
| File:PRO-LAD structure.png | PRO-LAD (6-propyl-6-nor-LSD) | 65527-63-1 | H | CH2CH2CH3 | CH2CH3 | CH2CH3 | - |
| File:IP-LAD structure.png | IP-LAD (6-isopropyl-6-nor-LSD) | H | CH(CH3)2 | CH2CH3 | CH2CH3 | - | |
| File:CYP-LAD.svg | CYP-LAD (TRALA-22; 6-cyclopropyl-6-nor-LSD) | H | C3H5 | CH2CH3 | CH2CH3 | - | |
| File:WO22-226408-13 structure.png | CPM-LAD (6-cyclopropylmethyl-6-nor-LSD) | H | CH2C3H5 | CH2CH3 | CH2CH3 | - | |
| File:BU-LAD-2D-skeletal.svg | BU-LAD (6-butyl-6-nor-LSD) | 96930-87-9 | H | CH2CH2CH2CH3 | CH2CH3 | CH2CH3 | - |
| File:PHENETHY-LAD structure.png | PHENETH-LAD (6-(phenethyl)-6-nor-LSD) | H | CH2CH2C6H5 | CH2CH3 | CH2CH3 | - | |
| File:WO22-226408-10 structure.png | NBOMe-LAD (6-(2-methoxybenzyl)-LAD) | H | CH2C6H4-o-OCH3 | CH2CH3 | CH2CH3 | - | |
| File:FLUOROETH-LAD structure.png | FLUORETH-LAD (FE-LAD; TRALA-15; 6-(2-fluoroethyl)-6-nor-LSD) | H | CH2CH2F | CH2CH3 | CH2CH3 | - | |
| File:WO22-226408-2 structure.png | FP-LAD (WO 2022/226408 Example 2; TRALA-16; 6-(3-fluoropropyl)-6-nor-LSD) | H | CH2CH2CH2F | CH2CH3 | CH2CH3 | - | |
| File:CE-LAD.svg | CE-LAD (CHLORETH-LAD; 6-(2-chloroethyl)-6-nor-LSD) | H | CH2CH2Cl | CH2CH3 | CH2CH3 | - | |
| File:ALD-52 image.svg | ALD-52 (1-acetyl-LSD) | 3270-02-8 | COCH3 | CH3 | CH2CH3 | CH2CH3 | - |
| File:1P-LSD Structural Formulae V.1.svg | 1P-LSD (1-propionyl-LSD) | 2349358-81-0 | COCH2CH3 | CH3 | CH2CH3 | CH2CH3 | - |
| File:1B-LSD Structure.svg | 1B-LSD (1-butanoyl-LSD) | 2349376-12-9 | COCH2CH2CH3 | CH3 | CH2CH3 | CH2CH3 | - |
| File:1V-LSD structure.svg | 1V-LSD (1-valeryl-LSD) | CO(CH2)3CH3 | CH3 | CH2CH3 | CH2CH3 | - | |
| File:1H-LSD structure.png | 1H-LSD (1-hexanoyl-LSD) | CO(CH2)4CH3 | CH3 | CH2CH3 | CH2CH3 | - | |
| File:1DD-LSD structure.png | 1DD-LSD (1-dodecanoyl-LSD) | CO(CH2)10CH3 | CH3 | CH2CH3 | CH2CH3 | - | |
| File:1CP-LSD structure.svg | 1cP-LSD (1-cyclopropylmethanoyl-LSD) | COC3H5 | CH3 | CH2CH3 | CH2CH3 | - | |
| File:1D-LSD.svg | 1D-LSD (1-(1,2-dimethylcyclobutane-1-carbonyl)-LSD) | COC4H5(CH3)2 | CH3 | CH2CH3 | CH2CH3 | - | |
| File:1F-LSD structure.png | 1F-LSD (1-(furan-2-carbonyl)-LSD) [58] | COC4H3O | CH3 | CH2CH3 | CH2CH3 | - | |
| File:1T-LSD structure.png | 1T-LSD (1-(thiophene-2-carbonyl)-LSD) | COC4H3S | CH3 | CH2CH3 | CH2CH3 | - | |
| File:1S-LSD structure.png | 1S-LSD (1-(3-(trimethylsilyl)propionyl)-LSD) | CO(CH2)2Si(CH3)3 | CH3 | CH2CH3 | CH2CH3 | - | |
| File:1P-AL-LAD structure.png | 1P-AL-LAD (1-propionyl-6-allyl-6-nor-LSD) | COCH2CH3 | H2C=CH-CH2 | CH2CH3 | CH2CH3 | - | |
| File:1CP-AL-LAD structure.png | 1cP-AL-LAD (1-cyclopropylmethanoyl-6-allyl-6-nor-LSD) | COC3H5 | H2C=CH-CH2 | CH2CH3 | CH2CH3 | - | |
| File:1T-AL-LAD structure.png | 1T-AL-LAD (1-(2-thienoyl)-6-allyl-6-nor-LSD)[59] | COC4H3S | H2C=CH-CH2 | CH2CH3 | CH2CH3 | - | |
| File:1P-ETH-LAD Structural Formulae V2.svg | 1P-ETH-LAD (1-propionyl-6-ethyl-6-nor-LSD) | COCH2CH3 | CH2CH3 | CH2CH3 | CH2CH3 | - | |
| File:1P-MIPLA structure.png | 1P-MIPLA (1-propionyl-lysergic acid methylisopropylamide) | COCH2CH3 | CH3 | CH(CH3)2 | CH3 | - | |
| File:MLD-41.svg | MLD-41 (1-methyl-LSD) | 4238-85-1 | CH3 | CH3 | CH2CH3 | CH2CH3 | - |
| File:1-Hydroxymethyl-LSD.svg | OML-632 (1-hydroxymethyl-LSD) | 114004-70-5 | CH2OH | CH3 | CH2CH3 | CH2CH3 | - |
| File:LSM-775.svg | LSM-775 (lysergic acid morpholide) | 4314-63-0 | H | CH3 | CH2CH2-O-CH2CH2 | - | |
| File:LPD-824-2d-skeletal.svg | LPD-824 (lysergic acid pyrrolidide) | 2385-87-7 | H | CH3 | (CH2)4 | - | |
| File:MPD-75 structure.png | MPD-75 (1-methyllysergic acid pyrrolidide) | 7221-79-6 | CH3 | CH3 | (CH2)4 | - | |
| File:LA-pyrrolinide structure.png | Lysergic acid pyrrolinide | ? | H | CH3 | CH2-CH=CH-CH2 | - | |
| File:LA-Cispyr structure.png | LA-Cispyr | ? | H | CH3 | cis-CH(CH3)-CH2CH2-CH(CH3) | - | |
| File:LSD-Pip.svg | LA-Pip (lysergic acid piperidide) | 50485-23-9 | H | CH3 | (CH2)5 | - | |
| File:LSD Azapane structure.png | LSD-Azepane (lysergic acid azepane)[60] | H | CH3 | (CH2)6 | - | ||
| File:LSD-azetidine.svg | Lysergic acid 2,4-dimethylazetidide (LA-SS-Az, LSZ) | 470666-31-0 | H | CH3 | CH2(CHCH3)2CH2 | - | |
| File:WO22-008627-1 structure.png | WO 2022/008627 Compound 1 [61] | H | CH3 | (CH2)2C(CH2)2O | - | ||
| File:LA-Aziridine structure.png | Lysergic acid-(2,3-dimethylaziridinyl)amide (LA-Aziridine) | ? | H | CH3 | ? | - | |
| File:2-bromo-LSD structure.svg | 2-Bromo-LSD (BOL-148; bromolysergide) | 478-84-2 | H | CH3 | CH2CH3 | CH2CH3 | 2-Br |
| File:2-iodo-LSD structure.png | 2-Iodo-LSD (IOL) | 3712-25-2 | H | CH3 | CH2CH3 | CH2CH3 | 2-I |
| File:2-oxo-LSD structure.png | 2-Oxo-LSD (2-oxy-LSD) | ? | H | CH3 | CH2CH3 | CH2CH3 | 2-Oxo |
| File:3-OH-2-oxo-LSD structure.png | 2-Oxo-3-hydroxy-LSD | ? | H | CH3 | CH2CH3 | CH2CH3 | 2-Oxo, 3-OH |
| File:1P-BOL-148 structure.png | 1P-BOL-148 (1-propionyl-2-bromo-LSD) | COCH2CH3 | CH3 | CH2CH3 | CH2CH3 | 2-Br | |
| File:12-Hydroxy-LSD.svg | 12-Hydroxy-LSD (12-OH-LSD) | 60573-89-9 | H | CH3 | CH2CH3 | CH2CH3 | 12-OH |
| File:12-MeO-LSD structure.png | 12-Methoxy-LSD (12-MeO-LSD) | 50484-99-6 | H | CH3 | CH2CH3 | CH2CH3 | 12-OMe |
| File:13-F-LSD structure.png | 13-Fluoro-LSD[62] | H | CH3 | CH2CH3 | CH2CH3 | 13-F | |
| File:13-Hydroxy-LSD.svg | 13-Hydroxy-LSD | H | CH3 | CH2CH3 | CH2CH3 | 13-OH | |
| File:13-MeO-LSD structure.png | 13-Methoxy-LSD | H | CH3 | CH2CH3 | CH2CH3 | 13-OMe | |
| File:14-HO-LSD structure.png | 14-Hydroxy-LSD | H | CH3 | CH2CH3 | CH2CH3 | 14-OH | |
| File:14-MeO-LSD structure.png | 14-Methoxy-LSD | H | CH3 | CH2CH3 | CH2CH3 | 14-OMe | |
Related compounds
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| Structure | Name | Chemical name | CAS # |
|---|---|---|---|
| File:2,3-Dihydro-LSD structure.png | 2,3-Dihydro-LSD (2,3-DH-LSD) | N,N-diethyl-6-methyl-9,10-didehydro-2,3-dihydroergoline-8β-carboxamide | ? |
| File:9,10-Dihydro-LSD structure.png | 9,10-Dihydro-LSD (9,10-DH-LSD) | (10ξ)-N,N-diethyl-6-methylergoline-8β-carboxamide | 3031-47-8 |
| File:Bromerguride.png | Bromerguride (2-bromolisuride) | 1,1-diethyl-3-(2-bromo-9,10-didehydro-6-methyl-8α-ergolinyl)urea | 83455-48-5 |
| File:Descarboxylysergic acid.svg | Descarboxylysergic acid | 6-methyl-9,10-didehydroergoline | 51867-17-5 |
| File:Disulergine structure.png | Disulergine | N,N-dimethyl-N'-(6-methylergoline-8α-yl)sulfamide | 59032-40-5 |
| File:Dosergoside structure.png | Dosergoside | N-((1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl)-6-methylergoline-8β-carboxamide | 87178-42-5 |
| File:Ergoline Structural Formulae V.1.svg | Ergoline | (6aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline | 478-88-6 |
| File:Etisulergine structure.png | Etisulergine | N,N-diethyl-N'-(6-methylergolin-8α-yl)sulfamide | 64795-23-9 |
| File:GYKI-32887 structure.png | GYKI-32887 | 8-((N-2-azidoethyl-N-methylsulfonylamino)methyl)-6-methylergol-8-ene | 78463-86-2 |
| File:JRT.svg | JRT | (7S)-N,N-diethyl-6-methyl-6,9-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(15),2,10,12(16),13-pentaene-4-carboxamide | ? |
| File:Lumi-LSD structure.png | Lumi-LSD (10-hydroxy-9,10-dihydro-LSD) | N,N-diethyl-10-hydroxy-6-methylergoline-8β-carboxamide | |
| File:Lysergine.svg | Lysergine | 9,10-didehydro-6,8β-dimethylergoline | 519-10-8 |
| File:Lysergol.svg | Lysergol | (6-methyl-9,10-didehydroergolin-8β-yl)methanol | 1413-67-8 |
| File:Lysergic acid chemical structure.svg | Lysergic acid | 6-methyl-9,10-didehydroergoline-8β-carboxylic acid | 82-58-6 |
| File:Lergotrile structure.png | Lergotrile | 2-chloro-6-methylergoline-8β-acetonitrile | 36945-03-6 |
| File:Lisuride.svg | Lisuride | 1,1-diethyl-3-(6-methyl-9,10-didehydroergolin-8α-yl)urea | 18016-80-3 |
| File:Proteguride structure.png | Proterguride (6-propyl-9,10-dihydrolisuride) | 1,1-diethyl-3-(6-n-propyl-8α-ergolinyl)urea | 77650-95-4 |
| File:Terguride.png | Terguride (9,10-dihydrolisuride) | N,N-diethyl-N'-[(8α)-6-methylergolin-8-yl]urea | 37686-84-3 |
See also
References
External links
Template:Psychedelics Template:Navboxes Script error: No such module "Navbox". Template:Chemical classes of psychoactive drugs
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- ↑ Parrish JC. Toward a molecular understanding of hallucinogen action. PhD thesis, Purdue University, 2006
- ↑ Trachsel D, et al. Lysergic acid derivatives with modified LSD-like action. US 2023/0414583
- ↑ Kruegel AC. Novel Ergolines and Methods of Treating Mood Disorders. Patent WO 2022/226408
- ↑ Brandt SD, Kavanagh PV, Gare S, Elliott SP, Stratford A, Halberstadt AL. Analytical and Pharmacological Characterization of 1-(Furan-2-Carbonyl)-LSD (1F-LSD) and Comparison With 1-(Thiophene-2-Carbonyl)-LSD (1T-LSD). Drug Test Anal. 2024 Dec 3. Script error: No such module "doi". Template:Pmid
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