PNU-181731

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]

PNU-181731

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
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

See also

• Lorcaserin
• PNU-22394
• PHA-57378

References

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.