Tenilapine

Tenilapine is an atypical antipsychotic which has never been marketed in the US.

Tenilapine
INN: tenilapine

Identifiers
IUPAC name (2E)-[5-(4-Methyl-1-piperazinyl)-9H-bisthieno[3,4-b:3',4'-e]azepin-9-ylidene]acetonitrile
CAS Number	82650-83-7 Y[PubChem]
PubChem CID	6450478
ChemSpider	4953083
UNII	D0U312O2BE
ChEMBL	ChEMBL2105472
CompTox Dashboard (EPA)	DTXSID201336787
Chemical and physical data
Formula	C17H16N4S2
Molar mass	340.46 g·mol−1
3D model (JSmol)	Interactive image
SMILES CN1CCN(CC1)C2=NC3=CSC=C3/C(=C/C#N)/C4=CSC=C42
InChI InChI=1S/C17H16N4S2/c1-20-4-6-21(7-5-20)17-15-10-22-8-13(15)12(2-3-18)14-9-23-11-16(14)19-17/h2,8-11H,4-7H2,1H3/b12-2+ Key:RVQVUMIXBGFJLZ-SWGQDTFXSA-N

Pharmacodynamics

Tenilapine has a relatively high affinity for the 5-HT_2A receptor, and relatively low (micromolar) affinities for dopamine receptors.

Binding affinities

Receptor	Ki (nM)
D2	1584[1]
D4	721±300[1]
5-HT2A	40[1]

The ratio of D₂ to D₄ bonding is similar to that of clozapine.^[1] Like many other atypical antipsychotics, it is a potent 5-HT_2C antagonist.^[2]

References

1. Roth BL, Tandra S, Burgess LH, Sibley DR, Meltzer HY (August 1995). "D₄ dopamine receptor binding affinity does not distinguish between typical and atypical antipsychotic drugs". Psychopharmacology (Berl). 120 (3): 365–8. doi:10.1007/BF02311185. PMID 8524985. S2CID 13549491.
2. Di Giovanni G, Esposito E, Di Matteo V (2011). "The 5-HT_2C Receptor Subtype Controls Central Dopaminergic Systems: Evidence from Electrophysiological and Neurochemical Studies". 5-HT2C Receptors in the Pathophysiology of CNS Disease. The Receptors. Vol. 22. Totowa, NJ: Humana Press. pp. 215–247. doi:10.1007/978-1-60761-941-3_11. ISBN 978-1-60761-940-6.