PNU-181731

PNU-181731
Identifiers
	IUPAC name 2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole;
CAS Number	364344-56-9 ;
PubChem CID	9794092;
ChemSpider	7969859;
CompTox Dashboard (EPA)	DTXSID201045564 ;
Chemical and physical data
Formula	C12H14N2
Molar mass	186.25 g/mol g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C12=CC=CC=C1N3C(CCNCC3)=C2;
	InChI InChI=1S/C12H14N2/c1-2-4-12-10(3-1)9-11-5-6-13-7-8-14(11)12/h1-4,9,13H,5-8H2; Key:XORPZYQOYUSNCQ-UHFFFAOYSA-N;

PNU-181731 is a drug which acts as an agonist at serotonin 5-HT₂ receptors,^[1]^[2] with strongest binding affinity for the 5-HT_2C subtype at 4.8nM, and weaker 5-HT_2A affinity of 18nM. It has anxiolytic effects in animal studies with around one tenth the potency of alprazolam and no significant ataxia or other side effects noted.^[3]

References

^ Michael D Ennis et al. 2,3,4,5-Tetrahydro-1H-[1,4diazepino[1,7-a]indole compounds. US Patent 6734301, Priority date March 14, 2000]
^ Junya Shirai et al. Fused heterocyclic compound and use thereof. US Patent 8158617, Priority date May 16, 2006
^ Ennis, M. D.; Hoffman, R. L.; Ghazal, N. B.; Olson, R. M.; Knauer, C. S.; Chio, C. L.; Hyslop, D. K.; Campbell, J. E.; Fitzgerald, L. W.; Nichols, N. F.; Svensson, K. A.; McCall, R. B.; Haber, C. L.; Kagey, M. L.; Dinh, D. M. (2003). "2,3,4,5-Tetrahydro- and 2,3,4,5,11,11a-hexahydro-1H-\1,4]diazepino\1,7-a]indoles: New templates for 5-HT2C agonists". Bioorganic & Medicinal Chemistry Letters. 13 (14): 2369–72. doi:10.1016/S0960-894X(03)00403-7. PMID 12824036.

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[1] Michael D Ennis et al. 2,3,4,5-Tetrahydro-1H-[1,4diazepino[1,7-a]indole compounds. US Patent 6734301, Priority date March 14, 2000]

[2] Junya Shirai et al. Fused heterocyclic compound and use thereof. US Patent 8158617, Priority date May 16, 2006

[3] Ennis, M. D.; Hoffman, R. L.; Ghazal, N. B.; Olson, R. M.; Knauer, C. S.; Chio, C. L.; Hyslop, D. K.; Campbell, J. E.; Fitzgerald, L. W.; Nichols, N. F.; Svensson, K. A.; McCall, R. B.; Haber, C. L.; Kagey, M. L.; Dinh, D. M. (2003). "2,3,4,5-Tetrahydro- and 2,3,4,5,11,11a-hexahydro-1H-\1,4]diazepino\1,7-a]indoles: New templates for 5-HT2C agonists". Bioorganic & Medicinal Chemistry Letters. 13 (14): 2369–72. doi:10.1016/S0960-894X(03)00403-7. PMID 12824036.

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See also

References