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

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, etoperidone, mepiprazole, and others produce mCPP as a metabolite.

para-Substituted

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

Multiple substitutions

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

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.

By drug class

Activities

See also

  • Substituted α-alkyltryptamine
  • Substituted amphetamine
  • Substituted cathinone
  • Substituted methylenedioxyphenethylamine
  • Substituted phenethylamine
  • Substituted phenylmorpholine
  • Substituted tryptamine

References



Chemical structure of substituted piperazines. Substituted piperazines

US6844345B2 Piperazine derivatives Google Patents

scheme for synthesis of 2(Substituted aryl)Piperazine... Download

Substituted piperazines PsychonautWiki

Scheme 1. Synthetic approach of substituted pyrazolines. Download