Chemistry:Alpertine
Alpertine (INN, USAN; developmental code name WIN-31665) is a drug of the pertine group described as an antipsychotic, neuroleptic, and tranqulizer which was never marketed.[1][2][3]
Structurally, it is a substituted tryptamine and a piperazinylethylindole.[4] The drug is closely structurally related to other "pertines" including milipertine, oxypertine, and solypertine, which are also tryptamines and piperazinylethylindoles.[4]
The related drug oxypertine shows high affinity for the serotonin 5-HT2 and dopamine D2 receptors (Ki = 8.6 nM and 30 nM, respectively) and is also known to act as a catecholamine depleting agent.[5][6] Oxypertine, milipertine, and solypertine all antagonize the behavioral effects of tryptamine, a serotonin receptor agonist, and apomorphine, a dopamine receptor agonist, in animals.[5][7] Conversely however, alpertine was not effective, at least at doses of up to 10 mg/kg.[5][7] ortho-Methoxyphenylpiperazine (oMeOPP) has been said to be a metabolite of the related drugs milipertine and oxypertine.[8][9]
Alpertine was first described in the scientific literature by 1971.[1]
See also
- Pertine
References
- ↑ 1.0 1.1 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. 2014. p. 33. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA33. Retrieved 30 October 2024.
- ↑ Pharmaceutical Manufacturing Encyclopedia. Volumes 1-4. William Andrew Publishing. 2013. pp. 185–186. ISBN 978-0-8155-1856-3. https://books.google.com/books?id=_J2ti4EkYpkC&pg=PA185. Retrieved 30 October 2024.
- ↑ Drugs: Synonyms and Properties. Wiley. 2002. p. 422. ISBN 978-0-566-08491-1. https://books.google.com/books?id=QxcoEAAAQBAJ&pg=PA422. Retrieved 30 October 2024.
- ↑ 4.0 4.1 Progress in Medicinal Chemistry. Elsevier Science. 1996. p. 219. ISBN 978-0-08-086281-1. https://books.google.com/books?id=SDaZ4qcemf8C&pg=PA219. Retrieved 30 October 2024. "Pertines (class 7; Table 5.12) The pertines oxypertine, solypertine, milipertine, and alpertine are piperazinylethylindoles."
- ↑ 5.0 5.1 5.2 "Risperidone and related 5HT2/D2 antagonists: a new type of antipsychotic agent?". Progress in Medicinal Chemistry 33: 185–232. 1996. doi:10.1016/s0079-6468(08)70306-0. ISBN 978-0-444-82310-6. PMID 8776944.
- ↑ "Differential monoamine depletion by oxypertine in nerve terminals. Granulated synaptic vesicles in relation to depletion of norepinephrine, dopamine and serotonin". Zeitschrift für Zellforschung und Mikroskopische Anatomie 101 (3): 448–462. 1969. doi:10.1007/BF00335580. PMID 5362847.
- ↑ 7.0 7.1 "A systematic study of the pharmacological activities of dopamine antagonists". Life Sciences (Elsevier BV) 24 (24): 2201–2216. June 1979. doi:10.1016/0024-3205(79)90096-1. PMID 388130.
- ↑ "Current awareness of piperazines: pharmacology and toxicology". Drug Testing and Analysis 3 (7–8): 430–438. 2011. doi:10.1002/dta.307. PMID 21744514. "Furthermore, oMeOPP is a metabolite of some prescribed drugs: enciprazione, milipertine, urapidil, dropropizine and oxypertine.[1,47]".
- ↑ "Identification and quantitation of 1-arylpiperazines, metabolites resulting from side-chain cleavage of (4-substituted aryl-1-piperazinyl)alkyl heterocyclic derivatives in rat plasma and brain". Journal of Chromatography 283: 211–221. January 1984. doi:10.1016/s0021-9673(00)96256-3. PMID 6707118.
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