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 names	DAM-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
Metabolism	hepatic
Excretion	renal
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	4238-84-0 Y
PubChem CID	199478
ChemSpider	172668 Y
CompTox Dashboard (EPA)	DTXSID30962445
Chemical and physical data
Formula	C18H21N3O
Molar mass	295.386 g·mol−1
3D model (JSmol)	Interactive image
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
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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.