LA-MeO

Last updated

LA-MeO
LA-MeO structure.png
Clinical data
Other namesLSD-MeO; Lysergic acid ethyl-2-methoxyethylamide; N-Ethyl-N-(2-methoxyethyl)lysergamide; LEO O-methyl ether; N-Ethyl-N-(2-methoxyethyl)-6-methyl-9,10-didehydroergoline-8β-carboxamide
Drug class Serotonin receptor modulator; Serotonin 5-HT2A receptor agonist
ATC code
  • None
Identifiers
  • (6aR,9R)-N-ethyl-N-(2-methoxyethyl)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
Chemical and physical data
Formula C21H27N3O2
Molar mass 353.466 g·mol−1
3D model (JSmol)
  • COCCN(C(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)c[nH]3)CC
  • InChI=1S/C21H27N3O2/c1-4-24(8-9-26-3)21(25)15-10-17-16-6-5-7-18-20(16)14(12-22-18)11-19(17)23(2)13-15/h5-7,10,12,15,19,22H,4,8-9,11,13H2,1-3H3/t15-,19-/m1/s1
  • Key:BQPPMBUEDZCBOR-DNVCBOLYSA-N

LA-MeO, also known as lysergic acid ethyl-2-methoxyethylamide or as N-ethyl-N-(2-methoxyethyl)lysergamide, is a serotonin receptor modulator of the lysergamide family related to lysergic acid diethylamide (LSD). [1] [2] It is the O-methyl ether derivative of the LSD metabolite lysergic acid ethyl-2-hydroxyethylamide (LEO). [1] [2]

Contents

The drug shows high affinity for the serotonin 5-HT1A, 5-HT2A, and 5-HT2C receptors (Ki = 4.0 nM, 7.1 nM, and 7.8 nM, respectively). [1] [2] It acts as a potent partial agonist of the serotonin 5-HT2A receptor similarly to LSD, with an EC50 Tooltip half-maximal effective concentration of 30.3 nM and an Emax Tooltip maximal efficacy of 29.6% (relative to 8.4 nM and 22.4% in the case of LSD, respectively). [1] [2]

LA-MeO was first described in the scientific literature by Jason C. Parrish of the lab of David E. Nichols at Purdue University by 2007. [1] [2]

See also

References

  1. 1 2 3 4 5 Nichols DE (2012). "Structure–activity relationships of serotonin 5-HT 2A agonists". Wiley Interdisciplinary Reviews: Membrane Transport and Signaling. 1 (5): 559–579. doi: 10.1002/wmts.42 . ISSN   2190-460X . Retrieved 22 March 2025.
  2. 1 2 3 4 5 Parrish JC (30 October 2007). Toward a molecular understanding of hallucinogen action (Ph.D. thesis). Purdue University – via Purdue e-Pubs.
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