Alpertine Explained

Cas Number:27076-46-6
Pubchem:166547
Chemspiderid:145751
Unii:KYT38QTB4K
Kegg:D02635
Chebi:177808
Chembl:2104031
Synonyms:WIN31665; WIN-31,665; Win 31665
Iupac Name:ethyl 5,6-dimethoxy-3-[2-(4-phenylpiperazin-1-yl)ethyl]-1H-indole-2-carboxylate
C:25
H:31
N:3
O:4
Smiles:CCOC(=O)C1=C(C2=CC(=C(C=C2N1)OC)OC)CCN3CCN(CC3)C4=CC=CC=C4
Stdinchi: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
Stdinchikey:RXAVJRAUFOPBOO-UHFFFAOYSA-N

Alpertine (; 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.

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.[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.[7] Conversely however, alpertine was not effective, at least at doses of up to 10mg/kg. 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.

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 . 33.
  2. Book: Pharmaceutical Manufacturing Encyclopedia . William Andrew Publishing . Volumes 1-4 . 2013 . 978-0-8155-1856-3 . 30 October 2024 . 185–186.
  3. Book: Milne GW . Drugs: Synonyms and Properties . Wiley . 2002 . 978-0-566-08491-1 . 30 October 2024 . 422.
  4. 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..
  5. Megens AA, Kennis LE . Risperidone and related 5HT2/D2 antagonists: a new type of antipsychotic agent? . Progress in Medicinal Chemistry . 33 . 185–232 . 1996 . 8776944 . 10.1016/s0079-6468(08)70306-0 . 978-0-444-82310-6 .
  6. 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 .
  7. 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 .
  8. 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] .
  9. 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 .

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