IHCH-7086

IHCH-7086
Identifiers
	IUPAC name (6bR,10aS)-2,3,6b,7,8,9,10,10a-octahydro-8-[3-(2-methoxyphenyl)propyl]-3-methyl-1H-Pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline;
CAS Number	2957888-70-7 ;
PubChem CID	162421364;
Chemical and physical data
Formula	C24H31N3O
Molar mass	377.532 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN(CCN1[C@]2([H])[C@@]3([H])CN(CCCC4=CC=CC=C4OC)CC2)C5=C1C3=CC=C5;
	InChI InChI=InChI=1S/C24H31N3O/c1-25-15-16-27-21-12-14-26(13-6-8-18-7-3-4-11-23(18)28-2)17-20(21)19-9-5-10-22(25)24(19)27/h3-5,7,9-11,20-21H,6,8,12-17H2,1-2H3/t20-,21-/m0/s1; Key:WFYFRJAKNJVZMP-SFTDATJTSA-N;

IHCH-7086 is a drug which acts as an agonist at the 5-HT_2A serotonin receptor. It was derived by structural simplification of the 5-HT_2A antagonist atypical antipsychotic drug lumateperone along with several related compounds such as IHCH-7079, which was found to be a non-hallucinogenic biased 5-HT_2A agonist that was active in antidepressant assays but did not produce psychedelic-like responding in mice.^[1]^[2]^[3] The related structure IHCH-7113 was found to produce a positive head-twitch response in mice, suggesting likely hallucinogenic activity in humans.

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): 403–411. Bibcode:2022Sci...375..403C. doi:10.1126/science.abl8615. PMID 35084960. S2CID 246360313.

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[1] 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.

[2] 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.

[pmid35084960-3] 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): 403–411. Bibcode:2022Sci...375..403C. doi:10.1126/science.abl8615. PMID 35084960. S2CID 246360313.

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[2]

[3]

See also

References