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
[edit]Benzylpiperazines
[edit]-
1-Benzylpiperazine (BZP) -
1-Methyl-4-benzylpiperazine (MBZP) -
1,4-Dibenzylpiperazine (DBZP) -
-
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)
Phenylpiperazines
[edit]ortho-Substituted
[edit]- 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
[edit]- 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
[edit]- 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
[edit]-
2,3-Dichlorophenylpiperazine (2,3-DCPP) -
3,4-Dichlorophenylpiperazine (3,4-DCPP)
- 2,3-Methylphenylpiperazine (DMPP)
- 3-Trifluoromethyl-4-chlorophenylpiperazine (TFMCPP; PAL-179) – selective partial serotonin releasing agent[3]
Others
[edit]- 1-Phenylpiperazine (PP)
Other arylpiperazines
[edit]- 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
[edit]- Substituted α-alkyltryptamine
- Substituted amphetamine
- Substituted cathinone
- Substituted methylenedioxyphenethylamine
- Substituted phenethylamine
- Substituted phenylmorpholine
- Substituted tryptamine
References
[edit]- ^ 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.
- ^ 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.
- ^ a b 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.