CPM-LAD

  1. Home
  2. Wiki

CPM-LAD
Clinical data
Other namesCPMLAD; CYPM-LAD; CYPMLAD; 6-(Cyclopropylmethyl)-6-nor-LSD; N(6)-Cyclopropylmethyl-norLSD;
Drug classSerotonin receptor modulator; Serotonergic psychedelic; Hallucinogen
ATC code
  • None
Identifiers
  • (6aR,9R)-7-(cyclopropylmethyl)-N,N-diethyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline-9-carboxamide
PubChem CID
Chemical and physical data
FormulaC23H29N3O
Molar mass363.505 g·mol−1
3D model (JSmol)
  • CCN(CC)C(=O)[C@H]1CN([C@@H]2CC3=CNC4=CC=CC(=C34)C2=C1)CC5CC5
  • 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

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]

Pharmacology

[edit]

The drug showed affinity (Ki) 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

[edit]

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

[edit]

References

[edit]
  1. ^ a b c d e Pfaff RC, Huang X, Marona-Lewicka D, Oberlender R, Nichols DE (1994). "Lysergamides revisited" (PDF). NIDA Research Monograph. 146: 52–73. PMID 8742794.
  2. ^ a b c d e Nichols DE, Oberlender R, McKenna DJ (1991). "Stereochemical Aspects of Hallucinogenesis". In Watson RR (ed.). Biochemistry and Physiology of Substance Abuse. Vol. 3. Boca Raton, Fla.: CRC Press. pp. 1–39. ISBN 978-0-8493-4463-3. OCLC 26748320. TABLE 1 Effects of N-(6)-Alkyl Subtituents on LSD-Like Behavior and Serotonin Receptor Affinity in Rats [...]
  3. ^ a b c Hoffman AJ (1987). Synthesis and pharmacological evaluation of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives (Ph.D. thesis). Purdue University. Archived from the original on 29 June 2025. Retrieved 30 June 2025 – via ProQuest.
  4. ^ a b c WO 2022226408A1, Kruegel AC, "Novel ergolines and methods of treating mood disorders", published 25 April 2022, assigned to Gilgamesh Pharmaceuticals, Inc.  Example 13: Preparation of (6aR,9R)-N,N-diethyl-7-(cyclopropylmethyl)-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide (13) [...]
  5. ^ Shulgin A, Shulgin A (September 1997). TiHKAL: The Continuation. Berkeley, California: Transform Press. ISBN 0-9630096-9-9. OCLC 38503252.
  6. ^ US 2023/0414583, Trachsel D, Liechti ME, Lustenberger F, "Lysergic acid derivatives with modified LSD-like action", published 28 December 2023, assigned to Mind Medicine Inc. 
[edit]



Stub icon

This hallucinogen-related article is a stub. You can help Wikipedia by expanding it.