14-Methyl-LSD

14-Methyl-LSD
Clinical data
Other names14-Me-LSD; N,N-Diethyl-14-methyllysergamide; 9,10-Didehydro-N,N-diethyl-6,14-dimethylergoline-8β-carboxamide
Drug classSerotonin 5-HT2A receptor agonist; Possible psychedelic drug or hallucinogen
ATC code
  • None
Identifiers
  • (6aR,9R)-N,N-diethyl-3,7-dimethyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide
CAS Number
Chemical and physical data
FormulaC21H27N3O
Molar mass337.467 g·mol−1
3D model (JSmol)
  • CCN(C([C@@H](C1)C=C2C3=C4C(C[C@@]2([H])N1C)=CNC4=C(C)C=C3)=O)CC
  • InChI=1S/C21H27N3O/c1-5-24(6-2)21(25)15-9-17-16-8-7-13(3)20-19(16)14(11-22-20)10-18(17)23(4)12-15/h7-9,11,15,18,22H,5-6,10,12H2,1-4H3/t15-,18-/m1/s1
  • Key:PQZLFPIADBNNMA-CRAIPNDOSA-N

14-Methyl-LSD, or 14-Me-LSD, is a serotonin 5-HT2A receptor agonist and possible psychedelic drug of the lysergamide family related to the psychedelic drug lysergic acid diethylamide (LSD).[1] It is the derivative of LSD with a methyl group at the 14 position.[1]

The drug is a highly potent full agonist of the serotonin 5-HT2A receptor, with an EC50Tooltip half-maximal effective concentration of 0.5432 nM and an EmaxTooltip maximal efficacy of 100.5% in an IP-1 assay.[1] Conversely, it is a very weak partial agonist or antagonist of the serotonin 5-HT2B receptor, with an EC50 of 2.319 nM and an Emax of 9.838% in an IP-1 assay.[1]

The chemical synthesis of 14-methyl-LSD has been described.[1] The drug's 2-bromo derivative, 2-Br-14-Me-LSD, has also been described.[1] It is a potent serotonin 5-HT2A receptor agonist similarly to 14-methyl-LSD, but with reduced potency and efficacy in comparison.[1] According to the compounds' developers, 14-methyl-LSD may produce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, whereas 2-Br-14-Me-LSD may not produce the head-twitch response.[1]

14-Methyl-LSD was described by David E. Nichols and colleagues in association with 2A Biosciences as a key compound in a patent in 2025.[1]

See also

References

  1. ^ a b c d e f g h i WO patent 2025019454, Nichols DE, Smith, "Substituted ergolines", published 23 January 2025, assigned to 2A Biosciences Inc and Florida State University Research Foundation 
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