Substituted piperazine explained

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

Phenylpiperazines

See also: Phenylpiperazine.

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

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

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

Notes and 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 . 10.1080/14756360802048939 . 1475-6366 . 18770069. 85385527 .
2. Alghamdi . Saad . Alshehri . Mohammed M. . Asif . Mohammad . The Neuropharmacological Potential of Piperazine Derivatives: A Mini- Review . Mini-Reviews in Organic Chemistry . 2022 . en . 19 . 7 . 798–810 . 10.2174/1570193x19666220119120211.
3. Rothman RB, Partilla JS, Baumann MH, Lightfoot-Siordia C, Blough BE . 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 . April 2012 . 22271821 . 3364510 . 10.1124/jpet.111.188946 .