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Abandoned antipsychotic drug
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 piperidinyl indole .[ 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]
^ 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 .
^ Milne GW (2002). Drugs: Synonyms and Properties . Wiley. p. 676. ISBN 978-0-566-08491-1 . Retrieved 8 October 2024 .
^ 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 .
^ 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).
^ 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 .
^ 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 .
Tryptamines
1-Methylpsilocin
2-HO-NMT
2-Me-DET
2-Methyl-5-HT
2,N ,N -TMT
4,5-DHP-DMT
4-AcO-DALT
4-AcO-DET
4-AcO-DiPT
4-AcO-DPT
4-AcO-EPT
4-AcO-MALT
4-AcO-MET
4-AcO-MiPT
4-AcO-NMT
4-AcO-TMT
4-F-5-MeO-DMT
4-HO-5-MeO-DMT
4-HO-DALT
4-HO-DBT
4-HO-DET
4-HO-DiPT
4-HO-DPT
4-HO-DSBT
4-HO-EPT
4-HO-MALT
4-HO-MET
4-HO-McPT
4-HO-McPeT
4-HO-MiPT
4-HO-MPT
4-HO-MsBT
4-HO-NALT
4-HO-NMT
4-HO-PiPT
4-HO-pyr-T
4-HO-TMT
4-HT
4-MeO-DiPT
4-MeO-DMT
4-MeO-MiPT
4-PrO-DMT
4,5-MDO-DMT
4,5-MDO-DiPT
5-BT
5-Bromo-DMT
5-CT
5-Chloro-DMT
5-Ethoxy-DMT
5-Ethyl-DMT
5-Fluoro-DET
5-Fluoro-DMT
5-Fluoro-EPT
5-Fluoro-MET
5-HO-DiPT
5-HTP (oxitriptan)
5-MeO-2-TMT
5-MeO-34MPEMT
5-MeO-7,N ,N -TMT
5-MeO-DALT
5-MeO-DBT
5-MeO-DET
5-MeO-DiPT
5-MeO-DMT
5-MeO-DPT
5-MeO-EiPT
5-MeO-EPT
5-MeO-MALT
5-MeO-MET
5-MeO-MiPT
5-MeO-NMT
5-MeO-pyr-T
5-MeO-NBpBrT
5-MeO-T-NBOMe
5-MeS-DMT
5-Methoxytryptamine (5-MT; mexamine)
5-Methyl-DMT
5-Methyltryptamine
5-MT-NB3OMe
5-(Nonyloxy)tryptamine
5,6-MeO-MiPT
5,6-MDO-DiPT
5,6-MDO-DMT
5,6-MDO-MiPT
5,6-DHT
5,7-DHT
6-Fluoro-DMT
6-MeO-DMT
7-Methyl-DMT
Acetryptine (5-AT)
Aeruginascin (4-PO-TMT)
AGH-107
AGH-192
AH-494
ALiPT
Alpertine
Baeocystin (4-PO-NMT)
Benzotript (4-chlorobenzoyl-L -tryptophan)
Bufotenidine (5-HTQ)
Bufotenin (5-HO-DMT)
Convolutindole A
CP-132,484
DALT
DBT
Desformylflustrabromine
DET
DiPT
DMT
DPT
E-6801
E-6837
EiPT
EMDT
EPT
Ethocybin (4-PO-DET)
FGIN-127
FGIN-143
FT-104
HIOC
Idalopirdine
Indolylethylfentanyl
Indorenate
Iprocin (4-HO-DiPT)
Lespedamine
MET
Methylbutyltryptamine
Miprocin (4-HO-MiPT)
MiPT
MPT
Milipertine
MS-245
MSBT
N -Feruloylserotonin (moschamine)
NET
NMT
Norbaeocystin (4-PO-T)
NTBT
O-4310
O -Pivalylbufotenine
Oxypertine
PiPT
Psilacetin (O -acetylpsilocin; 4-AcO-DMT)
Psilocin (4-HO-DMT)
Psilocybin (4-PO-DMT)
Pyr-T
RS134-49
Serotonin (5-HT)
Solypertine
ST-1936
Tryptamine
Tryptophan
Yuremamine
Z2876442907
N -Acetyltryptaminesα-Alkyltryptamines
2,α-DMT
4-HO-αMT
4-HO-MPMI (lucigenol)
4-Me-αET
4-Me-αMT
5-Chloro-αMT
5-Ethoxy-αMT
5-Fluoro-αET
5-Fluoro-αMT
5-iPrO-αMT
5-MeO-α,N ,N -TMT
5-MeO-αET
5-MeO-αMT
5-MeO-MPMI
5-Methyl-αET
6-Fluoro-αMT
7-Chloro-αMT
7-Methyl-αET
α-Methyl-5-HTP
α-Methylmelatonin
α-Methylserotonin (5-HO-αMT)
α-Methyltryptophan (αMTP)
α,N -DMT (N -methyl-αMT)
α,N ,N -TMT
α,N ,O -TMS
αET (etryptamine)
αMT
AL-37350A (4,5-DHP-αMT)
BNC-210
BW-723C86
CP-135807
IPAP (α,N -DPT)
MPMI
Triptans Cyclized tryptamines
Bay R 1531
Ciclindole
Cyclic 3-OHM
Ergolines and lysergamides (e.g., LSD )
Flucindole
Harmala alkaloids and β-carbolines (e.g., 6-MeO-THH , 9-Me-BC , β-carboline (norharman) , harmaline , harmalol , harmane , harmine , pinoline , tetrahydroharmine , tryptoline )
Iboga alkaloids and related (e.g., DM-506 (ibogaminalog) , ibogaine , ibogamine , noribogaine , tabernanthalog , tabernanthine )
Metralindole
NDTDI
PHA-57378
PNU-22394
PNU-181731
RU-28306
Yohimbans (e.g., yohimbine , rauwolscine , spegatrine , corynanthine , ajmalicine , reserpine , deserpidine , rescinnamine )
Related compounds