Milipertine Explained

Cas Number:24360-55-2
Pubchem:32345
Chemspiderid:29982
Unii:WX1V67H28T
Kegg:D02673
Chembl:2105252
Synonyms:Millipertine; WIN18935; WIN-18,935; Win-18935
Iupac Name:5,6-dimethoxy-3-[2-[4-(2-methoxyphenyl)piperazin-1-yl]ethyl]-2-methyl-1H-indole
C:24
H:31
N:3
O:3
Smiles:CC1=C(C2=CC(=C(C=C2N1)OC)OC)CCN3CCN(CC3)C4=CC=CC=C4OC
Stdinchi:1S/C24H31N3O3/c1-17-18(19-15-23(29-3)24(30-4)16-20(19)25-17)9-10-26-11-13-27(14-12-26)21-7-5-6-8-22(21)28-2/h5-8,15-16,25H,9-14H2,1-4H3
Stdinchikey:XYAANYFFYIRFND-UHFFFAOYSA-N

Milipertine (; developmental code name WIN-18935) is a drug described as an antipsychotic, neuroleptic, and tranquilizer which was under development for the treatment of schizophrenia but was never marketed.[1] [2] [3] [4]

Structurally, it is a substituted tryptamine and a piperazinylethylindole.[5] [6] [7] The drug is closely structurally related to other "pertines" including alpertine, oxypertine, and solypertine, which are also tryptamines and piperazinylethylindoles.[8]

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.[9] [10] Oxypertine, milipertine, and solypertine all antagonize the behavioral effects of tryptamine, a serotonin receptor agonist, and apomorphine, a dopamine receptor agonist, in animals.[11] ortho-Methoxyphenylpiperazine (oMeOPP) has been said to be a metabolite of milipertine, as well as of oxypertine and several other drugs.[12] [13]

Milipertine produced troublesome side effects in clinical studies including orthostatic hypotension, drowsiness, extrapyramidal symptoms, elevated liver enzymes, and weight loss.[14] [15] The side effects of milipertine occurred too frequently and at doses well below those producing antipsychotic effects and its development was abandoned.

Milipertine was first described in the scientific literature by 1968.

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 . 825.
  2. Book: Negwer M . Organic-chemical Drugs and Their Synonyms: (an International Survey) . Akademie Verlag . 1994 . 978-3-05-500156-7 . 30 October 2024 . 2306.
  3. Book: Milne GW . Drugs: Synonyms and Properties . Wiley . 2002 . 978-0-566-08491-1 . 30 October 2024 . 429.
  4. Mielke DH, Gallant DM, Bishop MP . Milipertine: an early evaluation in severely ill schizophrenics . Current Therapeutic Research, Clinical and Experimental . 15 . 6 . 324–326 . June 1973 . 4197256 .
  5. 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..
  6. Book: Lednicer D, Mitscher LA . The Organic Chemistry of Drug Synthesis, Volume 2 . Wiley . Organic Chemistry Series of Drug Synthesis . 1980 . 978-0-471-04392-8 . 30 October 2024 . 341–343.
  7. Book: Lednicer D . Strategies for Organic Drug Synthesis and Design . Wiley . 2009 . 978-0-470-39959-0 . 30 October 2024 . 390.
  8. Book: Lajtha A . Alterations of Metabolites in the Nervous System . Springer US . Handbook of neurochemistry . 2013 . 978-1-4757-6740-7 . 30 October 2024 . 335.
  9. 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 .
  10. 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 .
  11. 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 .
  12. 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] .
  13. 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 .
  14. Book: FDA Clinical Experience Abstracts . Food and Drug Administration. . 1 . 1973 . 30 October 2024 . 1-PA15.
  15. Book: Heinzelman RV . Annual Reports in Medicinal Chemistry . Academic Press . v. 9 . 1974 . 978-0-08-058353-2 . 30 October 2024 . 3.

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