Substituted Piperazine

Short description: 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-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)

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

4-Chlorophenylpiperazine (pCPP)
4-Fluorophenylpiperazine (pFPP)
4-Methylphenylpiperazine (pMPP)
4-Methoxyphenylpiperazine (MeOPP)
4-Nitrophenylpiperazine (pNPP)
4-Trifluoromethylphenylpiperazine (pTFMPP)

Multiple substitutions

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

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

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.

References

↑ 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. https://doi.org/10.1080/14756360802048939.
↑ Alghamdi, Saad; Alshehri, Mohammed M.; Asif, Mohammad (2022). "The Neuropharmacological Potential of Piperazine Derivatives: A Mini- Review" (in en). Mini-Reviews in Organic Chemistry 19 (7): 798–810. doi:10.2174/1570193x19666220119120211. https://www.eurekaselect.com/article/120285.

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[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. https://doi.org/10.1080/14756360802048939.

[2] Alghamdi, Saad; Alshehri, Mohammed M.; Asif, Mohammad (2022). "The Neuropharmacological Potential of Piperazine Derivatives: A Mini- Review" (in en). Mini-Reviews in Organic Chemistry 19 (7): 798–810. doi:10.2174/1570193x19666220119120211. https://www.eurekaselect.com/article/120285.

v t e Piperazines
Simple piperazines (no additional rings)	1-Cyclohexylpiperazine Aminoethylpiperazine Diethylcarbamazine HEPPS Midafotel Piperazine PIPES
Phenylpiperazines	Acaprazine Antrafenine Aripiprazole Batoprazine Bifeprunox BRL-15,572 Ciprofloxacin CSP-2503 Dapiprazole DCPP DMPP Diphenylpiperazine Dropropizine EGIS-12,233 Elopiprazole Eltoprazine Enpiprazole Ensaculin Etoperidone Flesinoxan Fluanisone Flibanserin Fluprazine Itraconazole Ketoconazole Levodropropizine Lorpiprazole mCPP Mefway MeOPP Mepiprazole Naftopidil Naluzotan Naphthylpiperazine Nefazodone Niaprazine Oxypertine Pardoprunox pCPP pFPP Posaconazole S-14,506 S-14,671 S-15,535 SB-258,585 SB-271,046 SB-357,134 SB-399,885 Sonepiprazole TFMPP Tolpiprazole Trazodone Urapidil Vesnarinone Vilazodone Vortioxetine WAY-100,135 WAY-100,635
Benzylpiperazines	2C-B-BZP Befuraline Bifeprunox Buclizine BZP Chlorbenzoxamine DBZP Fipexide Imatinib MBZP MDBZP Meclozine Methoxypiperamide Piberaline Piribedil Sunifiram Trimetazidine Vesnarinone
Diphenylalkylpiperazines (benzhydrylalkylpiperazines)	AD-1211 Almitrine Amperozide BRL-15,572 Buclizine BW373U86 Cetirizine Chlorbenzoxamine Chlorcyclizine Cinnarizine Clocinizine Cyclizine DBL-583 Diphenpipenol Diphenylmethylpiperazine Dotarizine DPI-221 DPI-287 DPI-3290 GBR-12,783 GBR-12,935 GBR-13,069 GBR-13,098 GBR-13,119 Hydroxyzine Lidoflazine Manidipine Meclozine MT-45 Oxatomide SNC-80 Vanoxerine
Pyrimidinylpiperazines	Buspirone Dasatinib Eptapirone Gepirone Ipsapirone Piribedil Prazitone Pyrimidinylpiperazine Revospirone Tandospirone Tirilazad Trimazosin Umespirone Zalospirone
Pyridinylpiperazines	Atevirdine Azaperone Delavirdine Mirtazapine Pyridinylpiperazine
Benzo(iso)thiazolylpiperazines	Lurasidone Perospirone Revospirone Tiospirone Ziprasidone
Tricyclics (piperazine attached via side chain)	Amoxapine Clopenthixol Clorotepine Clozapine Cyanothepin Doclothepin Docloxythepin Flupentixol Fluphenazine Isofloxythepin Loxapine Meperathiepin Metitepine Octomethothepin Olanzapine Opipramol Oxyclothepin Oxyprothepin Peradithiepin Perathiepin Perazine Perphenazine Pirenzepine Prochlorperazine Thiethylperazine Thiothixene Trifluoperazine Trifluthepin Zuclopenthixol
Others/Uncategorized	6-Nitroquipazine Azimilide Cinepazet Cinepazic acid Cinepazide Cyclohexylpiperazine EGIS-7625 Hexocyclium Indinavir JNJ-7777120 Lodenafil Mirodenafil PB-28 Quipazine Ranolazine SA-4503 Sildenafil Tadalafil Vardenafil VUF-6002 WY-46824 Zipeprol