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.

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)
• Mefeclorazine
• Vortioxetine

Enpiprazole is known to produce oCPP as a metabolite. It was initially anticipated to produce oMeOPP as a metabolite, but this proved 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, etoperidone, mepiprazole, and others produce mCPP as a metabolite.

para -Substituted

• 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)

Multiple substitutions

• 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

Others

• 1-Phenylpiperazine (PP)

Other arylpiperazines

• 1-(1-Naphthyl)piperazine (1-NP)
• 1-(2-Pyrimidinyl)piperazine (1-PP)
• 6-Chloro-2-(1-piperazinyl)quinoxaline (CPQ)
• 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.

By drug class

Antianginals

• Ranolazine
• Trimetazidine

Antidepressants

• Amoxapine
• Befuraline
• Buspirone
• Flesinoxan
• Gepirone
• Ipsapirone
• Nefazodone
• Piberaline
• Tandospirone
• Trazodone
• Vilazodone
• Vortioxetine
• Zalospirone

Antihistamines

• Buclizine
• Cetirizine
• Cinnarizine
• Cyclizine
• Hydroxyzine
• Levocetirizine
• Meclizine
• Niaprazine

Antiserotonergics

• EGIS-7625

Antipsychotics

• Typical Flupentixol Fluphenazine Perphenazine Prochlorperazine Thiothixene Trifluoperazine Zuclopenthixol Acetophenazine Carfenazine
• Atypical Amperozide Aripiprazole Clozapine Lurasidone Olanzapine Perospirone Ziprasidone Quetiapine Cariprazine

Recreational Drugs

• 4-Bromo-2,5-dimethoxy-1-benzylpiperazine (2C-B-BZP)
• 1-Benzylpiperazine (BZP)
• 2,3-Dichlorophenylpiperazine (DCPP)
• 1,4-Dibenzylpiperazine (DBZP)
• 4-Methyl-1-benzylpiperazine (MBZP)
• 3-Chlorophenylpiperazine (mCPP)
• 3,4-Methylenedioxy-1-benzylpiperazine (MDBZP)
• 4-Methoxyphenylpiperazine (MeOPP)
• Methoxypiperamide (MeOP or MEXP)
• 4-Chlorophenylpiperazine (pCPP)
• 4-Fluorophenylpiperazine (pFPP)
• 3-Trifluoromethylphenylpiperazine (TFMPP)

Urologicals

• Sildenafil
• Vardenafil

Others

• 6-Nitroquipazine
• Antrafenine
• Diethylcarbamazine
• Diphenazine
• Fipexide
• Imatinib
• NSI-189
• Pipobroman (antineoplastic agent)
• Quipazine
• Sunifiram (nootropic)
• Tolpiprazole (tranquilizer)

Activities

See also

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

External links

• . European Union Drugs Agency (EUDA).