1-Hydroxymethyl-LSD

OML-632, also known as 1-hydroxymethyllysergic acid diethylamide (1-hydroxymethyl-LSD), is a psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD).^{[1][2][3][4][5][6][7]}

1-Hydroxymethyl-LSD

Clinical data
Other names	OML-632; OML632; 1-Hydroxymethyllysergic acid diethylamide; 1-Hydroxymethyl-d-lysergic acid diethylamide; 1-Oxy-methyl-LSD; 1-Oxymethyl-LSD; Oxymethyl-LSD
Routes of administration	Oral
Drug class	Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code	None
Identifiers
IUPAC name (6aR,9R)-N,N-Diethyl-4-(hydroxymethyl)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
CAS Number	114004-70-5
Chemical and physical data
Formula	C21H27N3O2
Molar mass	353.466 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCN(C(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)cn3CO)CC
InChI InChI=1S/C21H27N3O2/c1-4-23(5-2)21(26)15-9-17-16-7-6-8-18-20(16)14(12-24(18)13-25)10-19(17)22(3)11-15/h6-9,12,15,19,25H,4-5,10-11,13H2,1-3H3/t15-,19-/m1/s1 Key:MCNBQMJSTKRHKK-DNVCBOLYSA-N

It has about 66% of the hallucinogenic potency of LSD in humans (which is stated as active at 50–100 μg) and about 59% of the antiserotonergic activity of LSD in the isolated rat uterus in vitro.^{[8][9][5][6][10][11]} However, OML-632 may simply act as a prodrug of LSD.^[6][11] The compound has also been said to serve as a metabolic intermediate in the demethylation of 1-methyl-LSD (MLD-41) into LSD.^[11]

OML-632 was first described in the scientific literature by 1957.^{[12][13][4][14]} The compound has been mistakenly referred to as "1-methoxy-LSD" or "1-MeO-LSD" in some publications.^[15][16][17]

See also

• MLD-41 (1-methyl-LSD)
• ALD-52 (1-acetyl-LSD)
• 1P-LSD (1-propionyl-LSD)