Substituted piperazine

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.

• 
  1-Benzylpiperazine (BZP)
• 
  1-Methyl-4-benzylpiperazine (MBZP)
• 
  1,4-Dibenzylpiperazine (DBZP)
• 
  3,4-Methylenedioxy-1-benzylpiperazine (MDBZP)
• 
  4-Bromo-2,5-dimethoxy-1-benzylpiperazine (2C-B-BZP)
• 
  Methoxypiperamide (MeOP, MEXP) ((4-methoxyphenyl)(4-methylpiperazin-1-yl)methanone)
• 
  Sunifiram (1-benzoyl-4-propanoylpiperazine)
• 
  3-Methylbenzylpiperazine (3-MeBZP)
• 
  Befuraline
  (also produces benzylpiperazine as a metabolite)
• 
  Fipexide
  (also produces substituted benzylpiperazine as a metabolite)
• 
  Piberaline
  (also produces benzylpiperazine as a metabolite)

• 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.

• 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.

• 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)

• 
  2,3-Dichlorophenylpiperazine (2,3-DCPP)
• 
  3,4-Dichlorophenylpiperazine (3,4-DCPP)

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

• 1-Phenylpiperazine (PP)

• 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.

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

• "BZP/piperazines". European Union Drugs Agency (EUDA).