Substituted piperazine

Class of chemical compounds

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

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

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

Multiple substitutions

  • 2,3-Methylphenylpiperazine (DMPP)
  • 3-Trifluoromethyl-4-chlorophenylpiperazine (TFMCPP)

Others

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.


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Simple piperazines
(no additional rings)PhenylpiperazinesBenzylpiperazinesDiphenylalkylpiperazines
(benzhydrylalkylpiperazines)PyrimidinylpiperazinesPyridinylpiperazinesBenzo(iso)thiazolylpiperazinesTricyclics
(piperazine attached via side chain)Others/Uncategorized