Mefeclorazine

Last updated

Mefeclorazine
Mefeclorazine.svg
Identifiers
  • 1-(2-chlorophenyl)-4-[2-(3,4-dimethoxyphenyl)ethyl]piperazine
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C20H25ClN2O2
Molar mass 360.88 g·mol−1
3D model (JSmol)
  • COC1=C(C=C(C=C1)CCN2CCN(CC2)C3=CC=CC=C3Cl)OC
  • InChI=1S/C20H25ClN2O2/c1-24-19-8-7-16(15-20(19)25-2)9-10-22-11-13-23(14-12-22)18-6-4-3-5-17(18)21/h3-8,15H,9-14H2,1-2H3
  • Key:PJDRMPCBIWKBJA-UHFFFAOYSA-N

Mefeclorazine (INN Tooltip International Nonproprietary Name) is a neuroleptic (antipsychotic) of the phenethylamine and arylpiperazine groups. [1] [2] [3]

Contents

Part of mefeclorazine's chemical structure is based on 3,4-dimethoxyphenethylamine (DMPEA or homoveratrylamine), which has structural similarity to the neurotransmitter dopamine. [1] Mefeclorazine was invented by Jack Mills of Eli Lilly in 1958. [4] Although it is not known to have ever been used clinically, [1] it is based on a chemically rational synthetic design.

The ortho-chlorophenylpiperazine (oCPP) moiety forms part of the molecular structure. [1] This precursor finds dual use in the synthesis of the arylpiperazines enpiprazole and KMUP-1.[ citation needed ]

See also

See also

References

  1. 1 2 3 4 Elks J, Ganellin CR (1990). Dictionary of drugs: Chemical Data, Structures, and Bibliographies (First ed.). Dordrecht: Springer. ISBN   978-1-4757-2085-3. Mefeclorazine, INN 1-(2-Chlorophenyl)-4-(3,4-dimethoxyphenethyl)-piperazine. SD 218-06 [1243-33-0] [...] C20H25ClN202 M 360.883 M-00061 Neuroleptic agent. [...]
  2. ↑ Ratouis R, Boissier JR, Dumont C (January 1965). "Synthesis and Pharmacological Study of New Piperazine Derivatives. II. Phenethylpiperazines". Journal of Medicinal Chemistry. 8 (1): 104–107. doi:10.1021/jm00325a021. PMID   14287237.
  3. ↑ Boissier JR (1963). "A new class of neuroleptics: N, N'-disubstituted piperazines". Psychopharmacol. Methods. Proc. Symp. 1961. Prague: 92–100.
  4. ↑ US 2927924,Mills J,"Phenethyl substituted piperazines",issued 8 March 1960, assigned to Eli Lilly & Co.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.