CPM-LAD

CPM-LAD, or CYPM-LAD, also known as 6-(cyclopropylmethyl)-6-nor-LSD, is a serotonin receptor modulator and putative psychedelic drug of the lysergamide family.^[1][2][3][4] It is the analogue of LSD in which the methyl group at the 6 position has been replaced with a cyclopropylmethyl group.^[1][2][3]

CPM-LAD

Clinical data
Other names	CPMLAD; CYPM-LAD; CYPMLAD; 6-(Cyclopropylmethyl)-6-nor-LSD; N(6)-Cyclopropylmethyl-norLSD;
Drug class	Serotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code	None
Identifiers
IUPAC name (6aR,9R)-7-(cyclopropylmethyl)-N,N-diethyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
PubChem CID	166091837
Chemical and physical data
Formula	C23H29N3O
Molar mass	363.505 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCN(CC)C(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)CC5CC5
InChI InChI=1S/C23H29N3O/c1-3-25(4-2)23(27)17-10-19-18-6-5-7-20-22(18)16(12-24-20)11-21(19)26(14-17)13-15-8-9-15/h5-7,10,12,15,17,21,24H,3-4,8-9,11,13-14H2,1-2H3/t17-,21-/m1/s1 Key:XTKDRKBVDJFYNW-DYESRHJHSA-N

Pharmacology

The drug showed affinity (K_i) values for serotonin receptors of 10.9 nM for serotonin-labeled 5-HT₁ receptors and 7.7 nM for ketanserin-labeled 5-HT₂ receptors.^[1][2] These affinities were very similar to but slightly lower than those of LSD.^[1][2] CPM-LAD fully substituted for LSD in rodent drug discrimination tests with an ED₅₀Tooltip median effective dose of 0.067 μmol/kg, relative to a dose of 0.046 μmol/kg in the case of LSD (with CPM-LAD about 1.5-fold less potent than LSD).^[1][2] Additional pharmacology for CPM-LAD has also been published.^[4] Unlike related lysergamides, CPM-LAD was not mentioned in Alexander Shulgin's 1997 book TiHKAL (Tryptamines I Have Known and Loved) and is not known to have been tested in humans.^[5]

History

CPM-LAD was first described in the scientific literature by Andrew Joseph Hoffman of the lab of David E. Nichols at Purdue University in 1987.^[3] Subsequently, it was patented by Gilgamesh Pharmaceuticals in 2022, who further studied and described its pharmacology.^[4] Derivatives of CPM-LAD have also been patented by Daniel Trachsel and Matthias Liechti and colleagues in association with MindMed.^[6]

See also

• Substituted lysergamide
• CYP-LAD