Solypertine

Last updated

Solypertine
Solypertine.svg
Clinical data
Other namesSolipertine; WIN18413; WIN-18,413; Win-18413; WIN 18413-2
Identifiers
  • 7-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-5H-[1,3]dioxolo[4,5-f]indole
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C22H25N3O3
Molar mass 379.460 g·mol−1
3D model (JSmol)
  • COC1=CC=CC=C1N2CCN(CC2)CCC3=CNC4=CC5=C(C=C43)OCO5
  • InChI=1S/C22H25N3O3/c1-26-20-5-3-2-4-19(20)25-10-8-24(9-11-25)7-6-16-14-23-18-13-22-21(12-17(16)18)27-15-28-22/h2-5,12-14,23H,6-11,15H2,1H3
  • Key:GIWODWVYEOAGQV-UHFFFAOYSA-N

Solypertine (INN Tooltip International Nonproprietary Name; developmental code name WIN-18413), also known as solypertine tartrate (USAN Tooltip United States Adopted Name) in the case of the tartrate salt, is a drug 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

References

  1. 1 2 Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 1105. ISBN   978-1-4757-2085-3 . Retrieved 30 October 2024.
  2. ↑ Negwer M (1994). Organic-chemical Drugs and Their Synonyms: (an International Survey). Akademie Verlag. p. 2064. ISBN   978-3-05-500156-7 . 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. 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. ISSN   0033-3166 . Retrieved 30 October 2024.
  5. ↑ Wylie DW, Archer S (September 1962). "Structure-Activity Relationships of 1-[3-Indolyl)alkyl]-4-arylpiperazines. A New Series of Tranquilizers". Journal of Medicinal and Pharmaceutical Chemistry. 5 (5). American Chemical Society (ACS): 932–943. doi:10.1021/jm01240a006. PMID   14056437.
  6. 1 2 Ellis GP, Luscombe DK (1996). Progress in Medicinal Chemistry. Elsevier Science. p. 219. ISBN   978-0-08-086281-1 . Retrieved 30 October 2024. Pertines (class 7; Table 5.12) The pertines oxypertine, solypertine, milipertine, and alpertine are piperazinylethylindoles.
  7. ↑ Ishar MP, Faruk A (2006). Syntheses of Organic Medicinal Compounds. Alpha Science. p. 48. ISBN   978-1-84265-280-0 . Retrieved 30 October 2024.
  8. 1 2 Megens AA, Kennis LE (1996). Risperidone and related 5HT2/D2 antagonists: a new type of antipsychotic agent?. Progress in Medicinal Chemistry. Vol. 33. pp. 185–232. doi:10.1016/s0079-6468(08)70306-0. ISBN   978-0-444-82310-6. PMID   8776944.
  9. ↑ Bak IJ, Hassler R, Kim JS (1969). "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. doi:10.1007/BF00335580. PMID   5362847. S2CID   32583722.
  10. ↑ Niemegeers CJ, Janssen PA (June 1979). "A systematic study of the pharmacological activities of dopamine antagonists". Life Sciences. 24 (24). Elsevier BV: 2201–2216. doi:10.1016/0024-3205(79)90096-1. PMID   388130.
  11. ↑ Elliott S (2011). "Current awareness of piperazines: pharmacology and toxicology". Drug Testing and Analysis. 3 (7–8): 430–438. 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. ↑ Caccia S, Notarnicola A, Fong MH, Benfenati E (January 1984). "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. doi:10.1016/s0021-9673(00)96256-3. PMID   6707118.
  13. ↑ Gordon M (2013). Psychopharmacological Agents. Medicinal chemistry. Academic Press. p. 297. ISBN   978-1-4832-7446-1 . Retrieved 30 October 2024.
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