{{Short description|Psychedelic drug}} {{cs1 config|name-list-style=vanc|display-authors=6}} {{Drugbox | Watchedfields = changed | verifiedrevid = 447574383 | image = DAM-57.svg | image_class = skin-invert-image | width = 165px | image2 = DAM-57 3D.png | image_class2 = bg-transparent | width2 = 200px
<!-- Clinical data --> | tradename = | routes_of_administration = Oral<ref name="TiHKAL" /> | class =
<!-- Legal status --> | legal_AU = | legal_CA = | legal_UK = | legal_US = Schedule I | legal_US_comment = Controlled in the United States via the Federal Analog Act but only if it is intended for human consumption.
<!-- Pharmacokinetic data --> | bioavailability = | protein_bound = | metabolism = | onset = | elimination_half-life = | duration_of_action = | excretion =
<!-- Identifiers --> | PubChem = 199478 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 172668 | CAS_number = 4238-84-0 | CAS_number_Ref = {{Cascite|correct|CAS}} | UNII_Ref = {{fdacite|correct|FDA}} | UNII = LX5MKR2EXX | synonyms = DAM-57; ''N'',''N''-Dimethyllysergamide; DAM; Lysergic acid dimethylamide
<!-- Chemical data --> | IUPAC_name = (6a''R'',9''R'')-''N'',''N''-dimethyl-7-methyl-4,6,6a,7,8,9- hexahydroindolo- [4,3-fg] quinoline- 9-carboxamide | C=18 | H=21 | N=3 | O=1 | SMILES = O=C(N(C)C)[C@@H]3C=C2c4cccc1c4c(c[nH]1)C[C@H]2N(C3)C | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | 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 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = FWHSERNVTGTIJE-MLGOLLRUSA-N }}
'''DAM-57''', also known as '''''N'',''N''-dimethyllysergamide''' ('''DAM''') or as '''lysergic acid dimethylamide''', is a 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 10{{nbsp}}times the dose 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 name="TiHKAL">{{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 | bibcode = 1955HChAc..38..421S | 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>
==See also== * Substituted lysergamide * Lysergic acid methylamide (LAM) * Lysergic acid dipropylamide (DPL) * Lysergic acid diallylamide (DAL)
==References== {{Reflist}}
==External links== * [https://isomerdesign.com/pihkal/explore/5324 DAM-57 - Isomer Design] * [https://www.erowid.org/library/books_online/tihkal/tihkal26.shtml LSD-25 (Discusses DAM-57) - TiHKAL - Erowid] * [https://isomerdesign.com/pihkal/read/tk/26 LSD-25 (Discusses DAM-57) - TiHKAL - Isomer Design]
{{Psychedelics}} {{Ergolines}}
Category:Carboxamides Category:Designer drugs Category:Dimethylamino compounds Category:Psychedelic lysergamides
{{Hallucinogen-stub}}