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PNU-181731 structure.png
  • 2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,7-a]indole
CAS Number
PubChem CID
Chemical and physical data
Molar mass186.258 g·mol−1
3D model (JSmol)
  • C12=CC=CC=C1N3C(CCNCC3)=C2
  • 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

PNU-181731 is a drug which acts as an agonist at serotonin 5-HT2 receptors,[1][2] with strongest binding affinity for the 5-HT2C subtype at 4.8nM, and weaker 5-HT2A 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]

See also[edit]


  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.