γ-Carboline

γ-Carboline, or gamma-carboline, also known as 5H-pyrido[4,3-b]indole is a nitrogen-containing tricyclic heterocycle. A large number of derivatives are known with varying pharmacological properties.^[1]^[2]^[3]^[4] Tetrahydrogenated γ-carbolines like 2MePI are serotonin 5-HT_2A receptor modulators.^[5] The pyridopyrroloquinoxalines are cyclized γ-carbolines and include serotonergic psychedelics like IHCH-7113, non-hallucinogenic serotonin 5-HT_2A receptor agonists like IHCH-7079, IHCH-7086, and ITI-1549, and serotonin 5-HT_2A receptor antagonists like lumateperone (ITI-007).^[6]^[7]^[8]

Chemical structures of γ-carboline and selected derivatives

γ-Carboline
2MePI
IHCH-7113

Quick facts Names, Identifiers ...

γ-Carboline
Names

Preferred IUPAC name 5H-Pyrido[4,3-b]indole
Other names 5H-γ-Carboline
Identifiers
CAS Number	244-69-9^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL12540
ChemSpider	115684
ECHA InfoCard	100.383.422
PubChem CID	130802
UNII	89407EP2HE^Y
CompTox Dashboard (EPA)	DTXSID80179147
InChI InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-7-12-6-5-11(9)13-10/h1-7,13H Key: RDMFHRSPDKWERA-UHFFFAOYSA-N
SMILES C1=CC=C2C(=C1)C3=C(N2)C=CN=C3
Properties
Chemical formula	C₁₁H₈N₂
Molar mass	168.20 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

References

[1]
Alekseyev RS, Kurki AV, Yurovskaya MA (2009). "γ-Carbolines and their hydrogenated derivatives. 1. Aromatic γ-carbolines: methods of synthesis, chemical and biological properties (review)". Chem Heterocycl Comp. 45 (8): 889–925. doi:10.1007/s10593-009-0373-9. S2CID 97096571.
[2]
Alekseyev RS, Kurkin AV, Yurovskaya MA (2011). "γ-Carbolines and their hydrogenated derivatives 3. Hydrogenated derivatives of γ-carbolines: chemical and biological properties (Review)". Chem Heterocycl Comp. 46 (10): 1169–1198. doi:10.1007/s10593-011-0652-0. S2CID 95229099.
[3]
Smirnova OB, Golovko TV, Granik VG (2011). "Carbolines. Part I: Comparison of some methods for the synthesis of α-, γ-, and δ-carbolines (a review)". Pharm Chem J. 44 (12): 654–678. doi:10.1007/s11094-011-0540-z. S2CID 7100718.
[4]
Smirnova OB, Golovko TV, Granik VG (2011). "Carbolines. Part 2: Comparison of some of the properties of α-, γ-, and δ-carbolines (Review)". Pharm Chem J. 45 (7): 389–400. doi:10.1007/s11094-011-0641-8. S2CID 26600701.
[5]
Rudin D, Ren X, Liechti ME, Huang N, Arias HR (March 2026). "Ibogalogs Activate the 5-HT2A Receptor through a Mechanism Involving Outward and Inward Movements of the Respective Transmembrane Segment TM6 and TM7". Neurochem Res. 51 (2). doi:10.1007/s11064-026-04727-5. PMID 41870698.
[6]
Cao D, Yu J, Wang H, Luo Z, Liu X, He L, Qi J, Fan L, Tang L, Chen Z, Li J, Cheng J, Wang S (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.
[7]
Dai J, Dan W, Zhang Y, Wang J (September 2018). "Recent developments on synthesis and biological activities of γ-carboline". Eur J Med Chem. 157: 447–461. doi:10.1016/j.ejmech.2018.08.015. PMID 30103193.
[8]
Duan W, Cao D, Wang S, Cheng J (January 2024). "Serotonin 2A Receptor (5-HT2AR) Agonists: Psychedelics and Non-Hallucinogenic Analogues as Emerging Antidepressants". Chem Rev. 124 (1): 124–163. doi:10.1021/acs.chemrev.3c00375. PMID 38033123.

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