Chemistry:Solypertine

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Solypertine (INN; developmental code name WIN-18413), also known as solypertine tartrate (USAN) in the case of the tartrate salt, is a drug of the pertine group described as an antiadrenergic (or adrenolytic/sympatholytic) and as also potentially possessing neuroleptic properties which was never marketed.[1][2][3][4][5]

Structurally, it is a substituted tryptamine and a piperazinylethylindole.[6] The drug is closely structurally related to other "pertines" including alpertine, milipertine, and oxypertine, which are also tryptamines and piperazinylethylindoles.[6] Solypertine can be synthesized from 5,6-methylenedioxyindole.[7]

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.[8][9] Oxypertine, milipertine, and solypertine all antagonize the behavioral effects of tryptamine, a serotonin receptor agonist, and apomorphine, a dopamine receptor agonist, in animals.[8][10] ortho-Methoxyphenylpiperazine (oMeOPP) has been said to be a metabolite of milipertine and oxypertine.[11][12]

Solypertine was first described in the scientific literature by 1962.[1][13]

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. 1105. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA1105. Retrieved 30 October 2024. 
  2. ↑ Organic-chemical Drugs and Their Synonyms: (an International Survey). Akademie Verlag. 1994. p. 2064. ISBN 978-3-05-500156-7. https://books.google.com/books?id=ywltAAAAMAAJ&q=solypertine. Retrieved 30 October 2024. 
  3. ↑ National Institutes of Health (U.S.); National Cancer Institute (U.S.) (1978). Cancer Treatment Reports. DHEW publication. U.S. Department of Health, Education, and Welfare, Public Health Service, National Institutes of Health. p. 58. https://books.google.com/books?id=BmUVaDSUkXQC&pg=PA58. Retrieved 30 October 2024. 
  4. ↑ Psychopharmacology Service Center (U.S.) (1962). Psychopharmacology Abstracts. DHEW publication. U.S. Department of Health, Education, and Welfare, Public Health Service. p. 972. https://books.google.com/books?id=_x4kIURvqacC&pg=PA972. Retrieved 30 October 2024. 
  5. ↑ "Structure-Activity Relationships of 1-[3-Indolyl)alkyl]-4-arylpiperazines. A New Series of Tranquilizers". Journal of Medicinal and Pharmaceutical Chemistry (American Chemical Society (ACS)) 5 (5): 932–943. September 1962. doi:10.1021/jm01240a006. PMID 14056437. 
  6. ↑ 6.0 6.1 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." 
  7. ↑ Syntheses of Organic Medicinal Compounds. Alpha Science. 2006. p. 48. ISBN 978-1-84265-280-0. https://books.google.com/books?id=CK31Zjf-UWMC&pg=PA48. Retrieved 30 October 2024. 
  8. ↑ 8.0 8.1 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. 
  9. ↑ "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. 
  10. ↑ "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. 
  11. ↑ "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]". 
  12. ↑ "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. 
  13. ↑ Psychopharmacological Agents. Medicinal chemistry. Academic Press. 2013. p. 297. ISBN 978-1-4832-7446-1. https://books.google.com/books?id=0SwXBQAAQBAJ&pg=PA297. Retrieved 30 October 2024. 



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