IHCH-8134

IHCH-8134
Clinical data
Drug class	Serotonin 5-HT2A receptor agonist
Identifiers
	IUPAC name (6bR,10aS)-8-(3-(2-methoxyphenyl)propyl)-1,2,6b,7,8,9,10,10a-octahydro-[1,4]oxazino[2,3,4-hi]pyrido[4,3-b]indole;
PubChem CID	172549469;
Chemical and physical data
Formula	C23H28N2O2
Molar mass	364.489 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [H][C@@]12[C@@](CCN(CCCC3=CC=CC=C3OC)C2)([H])N4CCOC5=C4C1=CC=C5;
	InChI InChI=1S/C23H28N2O2/c1-26-21-9-3-2-6-17(21)7-5-12-24-13-11-20-19(16-24)18-8-4-10-22-23(18)25(20)14-15-27-22/h2-4,6,8-10,19-20H,5,7,11-16H2,1H3/t19-,20-/m0/s1; Key:XIZOEKLHAJIDMD-PMACEKPBSA-N;

IHCH-8134 is a serotonin 5-HT_2A receptor agonist of the oxazinopyridoindole family. It was derived by structural simplification of the serotonin 5-HT_2A receptor antagonist and atypical antipsychotic lumateperone. Another related compound is the pyridopyrroloquinoxaline IHCH-7079, which was found to be a non-hallucinogenic biased serotonin 5-HT_2A receptor agonist that was active in antidepressant assays but did not produce psychedelic-like responding in mice.^[1]^[2]^[3]

References

↑ US 6552017, Robichaud AJ, Lee T, Deng W, Mitchell IS, Yang MG, Haydar S, Chen W, Mc Clung CD, Calvello EJ, Zawrotny DM, "Substituted heterocycle fused gamma-carbolines.", issued 22 April 2003, assigned to Bristol Myers Squibb Pharma Co.
↑ US 9315504, Tomesch JC, Li P, Yao W, Zhang Q, Beard JD, Thompson AS, Cheng H, Wennogle LP, "Preparation of 4-((6BR,10AS)-3-methyl-2,3,6B,9,10, 10A-hexahydro-1H-pyrido[3′,4′:4,5]pyrrolo [1,2,3-de]quinoxalin-8-(7H)-yl)-1-(4-fluorophenyl)-1-butanone or a pharmaceutically acceptable salt thereof", issued 19 April 2016, assigned to Intra Cellular Therapies Inc.
↑ Cao D, Yu J, Wang H, Luo Z, Liu X, He L, et al. (January 2022). "Structure-based discovery of nonhallucinogenic psychedelic analogs". Science. 375 (6579). New York, N.Y.: 403–411. Bibcode:2022Sci...375..403C. doi:10.1126/science.abl8615. PMID 35084960. S2CID 246360313.

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