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Dimethyllysergamide - Revision history
2026-05-12T20:37:40Z
Revision history for this page on the wiki
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2025-06-29T21:20:37Z
<p>See also.</p>
<p><b>New page</b></p><div>{{short description|Chemical compound}}<br />
{{cs1 config|name-list-style=vanc|display-authors=6}}<br />
{{Drugbox<br />
| Watchedfields = changed<br />
| verifiedrevid = 447574383<br />
| image = DAM-57.svg<br />
| width = 165px<br />
<br />
<!--Clinical data--><br />
| tradename = <br />
| legal_AU = <br />
| legal_CA = <br />
| legal_UK = <br />
| legal_US = Schedule I<br />
| legal_US_comment = Controlled in the United States via the [[Federal Analog Act]] but only if it is intended for human consumption.<br />
| routes_of_administration = [[Wiktionary:oral|Oral]]<br />
<br />
<!--Pharmacokinetic data--><br />
| metabolism = hepatic<br />
| excretion = renal<br />
<br />
<!--Identifiers--><br />
| PubChem = 199478<br />
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}<br />
| ChemSpiderID = 172668<br />
| CAS_number = 4238-84-0<br />
| CAS_number_Ref = {{Cascite|correct|CAS}}<br />
| UNII_Ref = {{fdacite|correct|FDA}}<br />
| UNII = LX5MKR2EXX<br />
| synonyms = DAM-57; ''N'',''N''-Dimethyllysergamide; DAM; Lysergic acid dimethylamide<br />
<br />
<!--Chemical data--><br />
| IUPAC_name = (6a''R'',9''R'')-''N'',''N''-dimethyl-7-methyl-4,6,6a,7,8,9- hexahydroindolo- [4,3-fg] quinoline- 9-carboxamide<br />
| C=18 | H=21 | N=3 | O=1 <br />
| SMILES = O=C(N(C)C)[C@@H]3C=C2c4cccc1c4c(c[nH]1)C[C@H]2N(C3)C<br />
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}<br />
| StdInChI = 1S/C18H21N3O/c1-20(2)18(22)12-7-14-13-5-4-6-15-17(13)11(9-19-15)8-16(14)21(3)10-12/h4-7,9,12,16,19H,8,10H2,1-3H3/t12-,16-/m1/s1<br />
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}<br />
| StdInChIKey = FWHSERNVTGTIJE-MLGOLLRUSA-N<br />
}}<br />
<br />
'''DAM-57''', also known as '''''N'',''N''-dimethyllysergamide''' ('''DAM''') or as '''lysergic acid dimethylamide''', is a [[Derivative (chemistry)|derivative]] of [[ergine]]. There has been a single report of observing N,N-dimethyl-D-lysergamide in the illicit drug market.<ref>{{cite journal | vauthors = Clark AB | title = Lysergic Acid Diethylamide and Lysergic Acid Dimethylamide | journal = Microgram | volume = 6 | pages = 37 | date = 1973 }}</ref> This compound did induce autonomic disturbances at oral levels of some ten times the dosage required for [[lysergic acid diethylamide]] (LSD), presumably in the high hundreds of micrograms. There is some disagreement as to whether there were psychic changes observed.<ref>{{CiteTiHKAL | pages = 26 }}; {{cite web | title = #26. LSD-25 | url = https://www.erowid.org/library/books_online/tihkal/tihkal26.shtml | work = Erowid }}</ref> It was first described in the [[scientific literature]] by [[Albert Hofmann]] and colleagues by 1955.<ref name="Hofmann_1955">{{cite journal | vauthors = Hofmann A, Stoll A | title = Amide der stereoisomeren Lysergsäuren und Dihydro‐lysergsäuren. 38. Mitteilung über Mutterkornalkaloide | journal = Helvetica Chimica Acta | volume = 38 | issue = 2 | pages = 421–433 | date = 1955 | doi = 10.1002/hlca.19550380207 | trans-title = Amides of stereoisomeric lysergic and dihydrolysergic acids. 38. Ergot alkaloids | issn = 0018-019X | url = https://onlinelibrary.wiley.com/doi/10.1002/hlca.19550380207 | access-date = 5 June 2025 | url-access = subscription }}</ref><br />
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==See also==<br />
* [[Substituted lysergamide]]<br />
* [[Lysergic acid methylamide]] (LAM)<br />
* [[Lysergic acid dipropylamide]] (DPL)<br />
* [[Lysergic acid diallylamide]] (DAL)<br />
<br />
==References==<br />
{{Reflist}}<br />
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{{Psychedelics}}<br />
{{Ergolines}}<br />
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[[Category:Designer drugs]]<br />
[[Category:Psychedelic lysergamides]]<br />
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{{Hallucinogen-stub}}</div>
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