Dimethyllysergamide

{{short description|Chemical compound}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Drugbox

| Watchedfields = changed

| verifiedrevid = 447574383

| image = DAM-57.svg

| width = 165px

| tradename =

| 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.

| routes_of_administration = Oral

| metabolism = hepatic

| excretion = renal

| 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

| IUPAC_name = (6aR,9R)-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.{{cite journal | vauthors = Clark AB | title = Lysergic Acid Diethylamide and Lysergic Acid Dimethylamide | journal = Microgram | volume = 6 | pages = 37 | date = 1973 }} 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.{{CiteTiHKAL | pages = 26 }}; {{cite web | title = #26. LSD-25 | url = https://www.erowid.org/library/books_online/tihkal/tihkal26.shtml | work = Erowid }} It was first described in the scientific literature by Albert Hofmann and colleagues by 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 }}