Dimethyllysergamide

N,N-Dimethyllysergamide or N,N-dimethyl-D-lysergamide (DAM-57) is a derivative of ergine. There has been a single report of observing N,N-dimethyl-D-lysergamide in the illicit drug market.[1] This compound did induce autonomic disturbances at oral levels of some ten times the dosage required for LSD, presumably in the high hundreds of micrograms. There is some disagreement as to whether there were psychic changes observed.[2]

Dimethyllysergamide
Clinical data
Other namesDAM-57, Lysergic acid dimethylamide
Routes of
administration		Oral
Legal status
Legal status
  • US: Schedule I Controlled in the United States via the Federal Analog Act but only if it is intended for human consumption.
Pharmacokinetic data
Metabolismhepatic
Excretionrenal
Identifiers
IUPAC name
  • (6aR,9R)-N,N-dimethyl-7-methyl-4,6,6a,7,8,9- hexahydroindolo- [4,3-fg] quinoline- 9-carboxamide
CAS Number
PubChem CID
ChemSpider
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H21N3O
Molar mass295.386 g·mol−1
3D model (JSmol)
SMILES
  • O=C(N(C)C)[C@@H]3C=C2c4cccc1c4c(c[nH]1)C[C@H]2N(C3)C
InChI
  • InChI=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 Y
  • Key:FWHSERNVTGTIJE-MLGOLLRUSA-N Y
  (verify)

References
  1. Clark AB (1973). "Lysergic Acid Diethylamide and Lysergic Acid Dimethylamide". Microgram. 6: 37.
  2. Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. p. 26. ISBN 0-9630096-9-9. OCLC 38503252.; "#26. LSD-25". Erowid.



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