Chemistry:Milipertine

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Milipertine (INN, USAN; developmental code name WIN-18935) is a drug of the pertine group described as an antipsychotic, neuroleptic, and tranquilizer which was under development for the treatment of schizophrenia but was never marketed.[1][2][3][4]

Structurally, it is a substituted tryptamine and a piperazinylethylindole.[5][6][7] The drug is closely structurally related to other "pertines" including alpertine, oxypertine, and solypertine, which are also tryptamines and piperazinylethylindoles.[5][6][8]

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.[9][10] Oxypertine, milipertine, and solypertine all antagonize the behavioral effects of tryptamine, a serotonin receptor agonist, and apomorphine, a dopamine receptor agonist, in animals.[9][11] ortho-Methoxyphenylpiperazine (oMeOPP) has been said to be a metabolite of milipertine, as well as of oxypertine and several other drugs.[12][13]

Milipertine produced troublesome side effects in clinical studies including orthostatic hypotension, drowsiness, extrapyramidal symptoms, elevated liver enzymes, and weight loss.[14][15][4] The side effects of milipertine occurred too frequently and at doses well below those producing antipsychotic effects and its development was abandoned.[14][15][4]

Milipertine was first described in the scientific literature by 1968.[1]

See also

  • Pertine
  • NBOMe

References

  1. ↑ 1.0 1.1 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. 2014. p. 825. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA825. Retrieved 30 October 2024. 
  2. ↑ Organic-chemical Drugs and Their Synonyms: (an International Survey). Akademie Verlag. 1994. p. 2306. ISBN 978-3-05-500156-7. https://books.google.com/books?id=ywltAAAAMAAJ&q=Milipertine. Retrieved 30 October 2024. 
  3. ↑ Drugs: Synonyms and Properties. Wiley. 2002. p. 429. ISBN 978-0-566-08491-1. https://books.google.com/books?id=QxcoEAAAQBAJ&pg=PA429. Retrieved 30 October 2024. 
  4. ↑ 4.0 4.1 4.2 "Milipertine: an early evaluation in severely ill schizophrenics". Current Therapeutic Research, Clinical and Experimental 15 (6): 324–326. June 1973. PMID 4197256. 
  5. ↑ 5.0 5.1 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." 
  6. ↑ 6.0 6.1 The Organic Chemistry of Drug Synthesis, Volume 2. Organic Chemistry Series of Drug Synthesis. Wiley. 1980. pp. 341–343. ISBN 978-0-471-04392-8. https://books.google.com/books?id=r-eqWrMoO18C&pg=PA341. Retrieved 30 October 2024. 
  7. ↑ Strategies for Organic Drug Synthesis and Design. Wiley. 2009. p. 390. ISBN 978-0-470-39959-0. https://books.google.com/books?id=fEwl6Qev-mUC&pg=PA390. Retrieved 30 October 2024. 
  8. ↑ Alterations of Metabolites in the Nervous System. Handbook of neurochemistry. Springer US. 2013. p. 335. ISBN 978-1-4757-6740-7. https://books.google.com/books?id=dYnSBwAAQBAJ&pg=PA335. Retrieved 30 October 2024. 
  9. ↑ 9.0 9.1 Risperidone and related 5HT2/D2 antagonists: a new type of antipsychotic agent?. Progress in Medicinal Chemistry. 33. 1996. pp. 185–232. doi:10.1016/s0079-6468(08)70306-0. ISBN 978-0-444-82310-6. 
  10. ↑ "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. 
  11. ↑ "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. 
  12. ↑ "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]". 
  13. ↑ "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. 
  14. ↑ 14.0 14.1 FDA Clinical Experience Abstracts. Food and Drug Administration.. 1973. p. 1-PA15. https://books.google.com/books?id=u5sNDOW57FwC&pg=RA1-PA15. Retrieved 30 October 2024. 
  15. ↑ 15.0 15.1 Annual Reports in Medicinal Chemistry. Academic Press. 1974. p. 3. ISBN 978-0-08-058353-2. https://books.google.com/books?id=rZBH1_7Tx6UC&pg=PA3. Retrieved 30 October 2024. 



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