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;
UNII	UVL6VJD7YC;
CompTox Dashboard (EPA)	DTXSID201045564 ;
Chemical and physical data
Formula	C12H14N2
Molar mass	186.258 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

^ US 6734301, Ennis ME, et al., "2,3,4,5-Tetrahydro-1H-[1,4]diazepino[1,7-a]indole compounds.", published May 11, 2004, assigned to Pharmacia and Upjohn Co Inc
^ US 8158617, Shirai J, et al., "Fused heterocyclic compound and use thereof.", published April 17, 2012, assigned to Takeda Pharmaceutical Co Ltd
^ Ennis MD, Hoffman RL, Ghazal NB, Olson RM, Knauer CS, Chio CL, et al. (July 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-HT(2C) agonists". Bioorganic & Medicinal Chemistry Letters. 13 (14): 2369–72. doi:10.1016/S0960-894X(03)00403-7. PMID 12824036.

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[1] US 6734301, Ennis ME, et al., "2,3,4,5-Tetrahydro-1H-[1,4]diazepino[1,7-a]indole compounds.", published May 11, 2004, assigned to Pharmacia and Upjohn Co Inc

[2] US 8158617, Shirai J, et al., "Fused heterocyclic compound and use thereof.", published April 17, 2012, assigned to Takeda Pharmaceutical Co Ltd

[3] Ennis MD, Hoffman RL, Ghazal NB, Olson RM, Knauer CS, Chio CL, et al. (July 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-HT(2C) agonists". Bioorganic & Medicinal Chemistry Letters. 13 (14): 2369–72. doi:10.1016/S0960-894X(03)00403-7. PMID 12824036.

[1]

[2]

[3]

Identifiers

IUPAC name 2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
CAS Number	364344-56-9^Y
PubChem CID	9794092
ChemSpider	7969859
UNII	UVL6VJD7YC
CompTox Dashboard (EPA)	DTXSID201045564
Chemical and physical data
Formula	C₁₂H₁₄N₂
Molar mass	186.258 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

See also

References