Tepirindole

Not to be confused with Tipindole.

Tepirindole

Clinical data
Other names	RU-27592; HR-592
Drug class	Atypical antipsychotic; Major tranquilizer
Identifiers
IUPAC name 5-chloro-3-(1-propyl-3,6-dihydro-2H-pyridin-4-yl)-1H-indole
CAS Number	72808-81-2
PubChem CID	68915
ChemSpider	62142
UNII	X235XX30GK
ChEMBL	ChEMBL2105413
CompTox Dashboard (EPA)	DTXSID30868175
Chemical and physical data
Formula	C16H19ClN2
Molar mass	274.79 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCCN1CCC(=CC1)C2=CNC3=C2C=C(C=C3)Cl
InChI InChI=1S/C16H19ClN2/c1-2-7-19-8-5-12(6-9-19)15-11-18-16-4-3-13(17)10-14(15)16/h3-5,10-11,18H,2,6-9H2,1H3 Key:ZRCUMOBNOPSLKM-UHFFFAOYSA-N

Tepirindole (INN Tooltip International Nonproprietary Name; developmental code names RU-27592, HR-592) is a tryptamine-related atypical antipsychotic and major tranquilizer which was never marketed. ^{[1] [2] [3] [4] [5]} It is similar in structure to tryptamines but is not technically a tryptamine itself and is instead a dihydropyridinylindole. ^{[1] [6]} The drug is said to act on dopamine D₂, serotonin 5-HT₂, and α₁-adrenergic receptors. ^{[3] [4]} It is a potent dopamine receptor antagonist but reportedly has little propensity to cause catalepsy and has been said to potentially be useful in treating the negative symptoms of schizophrenia. ^{[4] [5]} The drug may also act as a potent serotonin receptor agonist. ^[6] Tepirindole was first described in the literature by 1979. ^{[1] [6]}

See also

• Ciclindole
• Flucindole
• Sertindole

References

1. Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 1159. ISBN   978-1-4757-2085-3 . Retrieved 8 October 2024.
2. Milne GW (2002). Drugs: Synonyms and Properties. Wiley. p. 676. ISBN   978-0-566-08491-1 . Retrieved 8 October 2024.
3. Seeman P (1990). "Atypical neuroleptics: role of multiple receptors, endogenous dopamine, and receptor linkage". Acta Psychiatrica Scandinavica. Supplementum. 358: 14–20. doi:10.1111/j.1600-0447.1990.tb05280.x. PMID   1978482.
4. Vinick F, Heym JH (1987). "Chapter 1 Antipsychotic Agents". Annual Reports in Medicinal Chemistry. Vol. 22. Elsevier. p. 1–10. doi:10.1016/s0065-7743(08)61149-5. ISBN   978-0-12-040522-0. ISSN   0065-7743. Several potent blockers of DA receptors are also putative atypical antipsychotics. Tepirindole (HR-592, 25) has a high affinity for DA, 5-HT and NE receptors but has little propensity to cause catalepsy (78).
5. Gomita Y, Ichimaru Y, Moriyama M, Furuno K, Suemaru K, Osman FE, et al. (April 1990). "Behavioral effects of HR-592, a new derivative of indole". Japanese Journal of Pharmacology. 52 (4): 609–619. doi: 10.1254/jjp.52.609 . PMID   2342229.
6. Euvrard C, Boissier JR (April 1980). "Biochemical assessment of the central 5-HT agonist activity of RU 24969 (a piperidinyl indole)". European Journal of Pharmacology. 63 (1): 65–72. doi:10.1016/0014-2999(80)90117-x. PMID   6155275.