Solypertine Explained

Cas Number:4448-96-8
Cas Supplemental:
5591-43-5 (tartrate)
Pubchem:20517
Chemspiderid:19323
Unii:9BUF6DCO0C
Chembl:1739674
Synonyms:Solipertine; WIN18413; WIN-18,413; Win-18413; WIN 18413-2
Iupac Name:7-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-5H-[1,3]dioxolo[4,5-f]indole
C:22
H:25
N:3
O:3
Smiles:COC1=CC=CC=C1N2CCN(CC2)CCC3=CNC4=CC5=C(C=C43)OCO5
Stdinchi: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
Stdinchikey:GIWODWVYEOAGQV-UHFFFAOYSA-N

Solypertine (; developmental code name WIN-18413), also known as solypertine tartrate 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. 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 = 8.6nM and 30nM, 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.[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.[13]

Notes and References

  1. Book: Elks J . The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies . Springer US . 2014 . 978-1-4757-2085-3 . 30 October 2024 . 1105.
  2. Book: Negwer M . Organic-chemical Drugs and Their Synonyms: (an International Survey) . Akademie Verlag . 1994 . 978-3-05-500156-7 . 30 October 2024 . 2064.
  3. Book: National Institutes of Health (U.S.) . National Cancer Institute (U.S.) . Cancer Treatment Reports . U.S. Department of Health, Education, and Welfare, Public Health Service, National Institutes of Health . DHEW publication . v. 62, no. 1 . 1978 . 30 October 2024 . 58.
  4. Book: Psychopharmacology Service Center (U.S.) . Psychopharmacology Abstracts . U.S. Department of Health, Education, and Welfare, Public Health Service . DHEW publication . 1962 . 0033-3166 . 30 October 2024 . 972.
  5. Wylie DW, Archer S . Structure-Activity Relationships of 1-[3-Indolyl)alkyl]-4-arylpiperazines. A New Series of Tranquilizers . Journal of Medicinal and Pharmaceutical Chemistry . 5 . 5 . 932–943 . September 1962 . 14056437 . 10.1021/jm01240a006 . American Chemical Society (ACS) .
  6. Book: Ellis GP, Luscombe DK . Progress in Medicinal Chemistry . Elsevier Science . v. 33 . 1996 . 978-0-08-086281-1 . 30 October 2024 . 219 . Pertines (class 7; Table 5.12) The pertines oxypertine, solypertine, milipertine, and alpertine are piperazinylethylindoles..
  7. Book: Ishar MP, Faruk A . Syntheses of Organic Medicinal Compounds . Alpha Science . 2006 . 978-1-84265-280-0 . 30 October 2024 . 48.
  8. Book: Megens AA, Kennis LE . Risperidone and related 5HT2/D2 antagonists: a new type of antipsychotic agent? . 33 . 185–232 . 1996 . 8776944 . 10.1016/s0079-6468(08)70306-0 . 978-0-444-82310-6 . Progress in Medicinal Chemistry .
  9. Bak IJ, Hassler R, Kim JS . Differential monoamine depletion by oxypertine in nerve terminals. Granulated synaptic vesicles in relation to depletion of norepinephrine, dopamine and serotonin . Zeitschrift Fur Zellforschung und Mikroskopische Anatomie . 101 . 3 . 448–462 . 1969 . 5362847 . 10.1007/BF00335580 . 32583722 .
  10. Niemegeers CJ, Janssen PA . A systematic study of the pharmacological activities of dopamine antagonists . Life Sciences . 24 . 24 . 2201–2216 . June 1979 . 388130 . 10.1016/0024-3205(79)90096-1 . Elsevier BV .
  11. Elliott S . Current awareness of piperazines: pharmacology and toxicology . Drug Testing and Analysis . 3 . 7–8 . 430–438 . 2011 . 21744514 . 10.1002/dta.307 . 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 . 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 . 6707118 . 10.1016/s0021-9673(00)96256-3 .
  13. Book: Gordon M . Psychopharmacological Agents . Academic Press . Medicinal chemistry . 2013 . 978-1-4832-7446-1 . 30 October 2024 . 297.

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