Tepirindole

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 (INNTooltip 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]

1. ^ ^{a b c} 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. ^ ^{a b} 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. ^ ^{a b c} 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. ^ ^{a b} 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. ^ ^{a b c} 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.

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