LA-MeO

Pharmaceutical compound From Wikipedia, the free encyclopedia

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]

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 classSerotonin receptor modulator; Serotonin 5-HT2A receptor agonist
ATC code
  • None
FormulaC21H27N3O2
Quick facts Clinical data, Other names ...
LA-MeO
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 classSerotonin 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
FormulaC21H27N3O2
Molar mass353.466 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
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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 EC50Tooltip half-maximal effective concentration of 30.3 nM and an EmaxTooltip 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

External links

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