IHCH-7079

IHCH-7079
Identifiers
	IUPAC name (6bR,10aS)-2,3,6b,7,8,9,10,10a-octahydro-8-[2-(2-methoxyphenyl)ethyl]-3-methyl-1H-Pyrido[3′,4′:4,5]pyrrolo[1,2,3-de]quinoxaline;
CAS Number	2957888-63-8 ;
PubChem CID	169488014;
Chemical and physical data
Formula	C23H29N3O
Molar mass	363.505 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN(CCN1[C@]2([H])[C@@]3([H])CN(CCC4=CC=CC=C4OC)CC2)C5=C1C3=CC=C5;
	InChI InChI=1S/C23H29N3O/c1-24-14-15-26-20-11-13-25(12-10-17-6-3-4-9-22(17)27-2)16-19(20)18-7-5-8-21(24)23(18)26/h3-9,19-20H,10-16H2,1-2H3/t19-,20-/m0/s1; Key:FCGZRBNMPIAEDK-PMACEKPBSA-N;

IHCH-7079 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-7086, 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