Lysergamides

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File:Lysergamides.svg
The lysergamide core, with common substitution positions denoted.

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]

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Doses, potencies, and durations of LSD and its analogues
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

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Lysergamides, tabulated by structure
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

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External links

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