Lysergic acid methylamide

Lysergic acid methylamide (LAM), also known as N-methyllysergamide (NM-LA), is a serotonin receptor modulator of the lysergamide family related to the psychedelic drug lysergic acid diethylamide (LSD).^[1][2][4] It is the N-methyl derivative of ergine (lysergic acid amide; LSA) and the analogue of LSD in which the N,N-diethyl groups have been replaced with one N-methyl group.^[1][2][4]

Other namesLysergic acid methylamide; LAM; Lysergic acid monomethylamide; LA-methylamide; LA-monomethylamide; N-Methyllysergamide; NM-LA; N-Methyl-LSA; N-Methylergine; N,6-Dimethyl-9,10-didehydroergoline-8β-carboxamide

Routes of
administrationOral^[1][2][3]

Drug classSerotonin receptor modulator

ATC code

• None

Quick facts Clinical data, Other names ...

Lysergic acid methylamide

Clinical data
Other names	Lysergic acid methylamide; LAM; Lysergic acid monomethylamide; LA-methylamide; LA-monomethylamide; N-Methyllysergamide; NM-LA; N-Methyl-LSA; N-Methylergine; N,6-Dimethyl-9,10-didehydroergoline-8β-carboxamide
Routes of administration	Oral[1][2][3]
Drug class	Serotonin receptor modulator
ATC code	None
Identifiers
IUPAC name (6aR,9R)-N,7-dimethyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
CAS Number	50485-06-8
PubChem CID	56841679
ChemSpider	21161369
CompTox Dashboard (EPA)	DTXSID50198507
Chemical and physical data
Formula	C17H19N3O
Molar mass	281.359 g·mol−1
3D model (JSmol)	Interactive image
SMILES CNC(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)C
InChI InChI=1S/C17H19N3O/c1-18-17(21)11-6-13-12-4-3-5-14-16(12)10(8-19-14)7-15(13)20(2)9-11/h3-6,8,11,15,19H,7,9H2,1-2H3,(H,18,21)/t11-,15-/m1/s1 Key:NINBUXQQTOVMAB-IAQYHMDHSA-N

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The drug is active in humans at a dose of approximately 500 μg and has roughly 20% of the potency of LSD as a drug.^[1][2][3] However, it has been said to produce autonomic effects but to produce no psychoactive or hallucinogenic effects at this dose.^[3][2][5] The drug has about 6.3% of the antiserotonergic potency of LSD in the isolated rat uterus in vitro.^[4][3][6][7]

LAM was first described in the scientific literature by Albert Hofmann and colleagues by 1955.^{[8][9][10][11]}