Substituted piperazine

Substituted piperazines are a class of chemical compounds based on a piperazine core.[1] Some are used as recreational drugs and some are used in scientific research.[2]

List of substituted piperazines

Benzylpiperazines

Phenylpiperazines

ortho-Substituted

  • 2-Chlorophenylpiperazine (oCPP)
  • 2-Methylphenylpiperazine (oMPP)
  • 2-Methoxyphenylpiperazine (oMeOPP)
  • Vortioxetine

Enpiprazole is known to produce oCPP as a metabolite.

Enciprazine was initially anticipated to produce oMeOPP as a metabolite, but this turned out not to be the case.

meta-Substituted

  • 3-Chlorophenylpiperazine (mCPP)
  • 3-Methoxyphenylpiperazine (mMeOPP)
  • 3-Trifluoromethylphenylpiperazine (TFMPP)
  • 1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine (3C-PEP)

Trazodone, nefazodone, mepiprazole, and others produce mCPP as a metabolite.

para-Substituted

  • 4-Chlorophenylpiperazine (pCPP)
  • 4-Fluorophenylpiperazine (pFPP)
  • 4-Methylphenylpiperazine (pMPP)
  • 4-Methoxyphenylpiperazine (MeOPP)
  • 4-Nitrophenylpiperazine (pNPP; PAL-175) – selective partial serotonin releasing agent[3]
  • 4-Trifluoromethylphenylpiperazine (pTFMPP)

Multiple substitutions

  • 2,3-Methylphenylpiperazine (DMPP)
  • 3-Trifluoromethyl-4-chlorophenylpiperazine (TFMCPP; PAL-179) – selective partial serotonin releasing agent[3]

Others

  • 1-Phenylpiperazine (PP)

Other arylpiperazines

  • 1-(1-Naphthyl)piperazine (1-NP)
  • 1-(2-Pyrimidinyl)piperazine (1-PP)
  • ORG-12962 (1-(5-trifluoromethyl-6-chloropyridin-2-yl)piperazine)
  • Quipazine (2-piperazin-1-ylquinoline)

Many azapirones such as buspirone, gepirone, and tandospirone produce 1-PP as a metabolite.

See also

References

  1. Laras, Y.; Garino, C.; Dessolin, J.; Weck, C.; Moret, V.; Rolland, A.; Kraus, J.-L. (2009-02-01). "New N4-substituted piperazine naphthamide derivatives as BACE-1 inhibitors". Journal of Enzyme Inhibition and Medicinal Chemistry. 24 (1): 181–187. doi:10.1080/14756360802048939. ISSN 1475-6366. PMID 18770069. S2CID 85385527.
  2. Alghamdi, Saad; Alshehri, Mohammed M.; Asif, Mohammad (2022). "The Neuropharmacological Potential of Piperazine Derivatives: A Mini- Review". Mini-Reviews in Organic Chemistry. 19 (7): 798–810. doi:10.2174/1570193x19666220119120211.
  3. 1 2 Rothman RB, Partilla JS, Baumann MH, Lightfoot-Siordia C, Blough BE (April 2012). "Studies of the biogenic amine transporters. 14. Identification of low-efficacy "partial" substrates for the biogenic amine transporters". J Pharmacol Exp Ther. 341 (1): 251–262. doi:10.1124/jpet.111.188946. PMC 3364510. PMID 22271821.


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