14-Methyl-LSD

vanc 6 14-Methyl-LSD.svg skin-invert-image 175px Serotonin 5-HT2A receptor agonist; Possible psychedelic drug or hallucinogen None 3069948-26-8 14-Me-LSD; N,N-Diethyl-14-methyllysergamide; 9,10-Didehydro-N,N-diethyl-6,14-dimethylergoline-8β-carboxamide (6aR,9R)-N,N-diethyl-3,7-dimethyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinoline-9-carboxamide 21 27 3 1 CCN(C([C@@H](C1)C=C2C3=C4C(C[C@@]2([H])N1C)=CNC4=C(C)C=C3)=O)CC 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 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 lysergic acid diethylamide (LSD). WO 2025019454 Nichols DE, Smith patent Substituted ergolines 23 January 2025 15 July 2024 15 July 2024 2A Biosciences Inc Florida State University Research Foundation https://patents.google.com/patent/WO2025019454A2/en?oq=WO2025019454 It is the derivative of LSD with a methyl group at the 14 position. The drug is a highly potent full agonist of the serotonin 5-HT2A receptor, with an EC50 half-maximal effective concentration of 0.5432nM and an Emax maximal efficacy of 100.5% in an IP-1 assay. Conversely, it is a very weak partial agonist or antagonist of the serotonin 5-HT2B receptor, with an EC50 half-maximal effective concentration of 2.319nM and an Emax maximal efficacy of 9.838% in an IP-1 assay. The chemical synthesis of 14-methyl-LSD has been described. The drug's 2-bromo derivative, 2-Br-14-Me-LSD, has also been described. It is a potent serotonin 5-HT2A receptor agonist similarly to 14-methyl-LSD, but with reduced potency and efficacy in comparison. 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. 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. See also Substituted lysergamide 14-Methoxy-LSD 14-Hydroxy-LSD 7-Methylpsilocin (BMB-A39a) 7-Methyl-DMT 7-Me-5-MeO-DMT References Category:5-HT2A agonists Category:5-HT2B agonists Category:5-HT2B antagonists Category:David E. Nichols Category:Diethylamides Category:Lysergamides Category:Methyl compounds