Alpertine

Alpertine
Clinical data
Other namesWIN31665; WIN-31,665; Win 31665
Identifiers
  • ethyl 5,6-dimethoxy-3-[2-(4-phenylpiperazin-1-yl)ethyl]-1H-indole-2-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H31N3O4
Molar mass437.540 g·mol−1
3D model (JSmol)
  • CCOC(=O)C1=C(C2=CC(=C(C=C2N1)OC)OC)CCN3CCN(CC3)C4=CC=CC=C4
  • InChI=1S/C25H31N3O4/c1-4-32-25(29)24-19(20-16-22(30-2)23(31-3)17-21(20)26-24)10-11-27-12-14-28(15-13-27)18-8-6-5-7-9-18/h5-9,16-17,26H,4,10-15H2,1-3H3
  • Key:RXAVJRAUFOPBOO-UHFFFAOYSA-N

Alpertine (INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name; developmental code name WIN-31665) is a drug 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]

References

  1. ^ a b Elks J (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 33. ISBN 978-1-4757-2085-3. Retrieved 30 October 2024.
  2. ^ Pharmaceutical Manufacturing Encyclopedia. Volumes 1-4. William Andrew Publishing. 2013. pp. 185–186. ISBN 978-0-8155-1856-3. Retrieved 30 October 2024.
  3. ^ Milne GW (2002). Drugs: Synonyms and Properties. Wiley. p. 422. ISBN 978-0-566-08491-1. Retrieved 30 October 2024.
  4. ^ a b 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.
  5. ^ a b c Megens AA, Kennis LE (1996). "Risperidone and related 5HT2/D2 antagonists: a new type of antipsychotic agent?". Progress in Medicinal Chemistry. 33: 185–232. doi:10.1016/s0079-6468(08)70306-0. ISBN 978-0-444-82310-6. PMID 8776944.
  6. ^ 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.
  7. ^ a b 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.
  8. ^ 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]
  9. ^ 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.