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
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
+ Compound Serotonin Norepinephrine Dopamine Type Ref 1-Benzylpiperazine (BZP) 6050–>100000 62.2–68 175–600 NDRA 1-Phenylpiperazine (PP) 880 186 2530 SNRA 2-Me-PP (oMPP) PAL-169 175 39.1 296–542 SNDRA 2-OMe-PP (oMeOPP) 2-TFM-PP (oTFMPP) 570 350 11200 SNRA 2-SMe-PP (oMTPP) 270 >10000 >10000 SRA 2-Et-PP (oEtPP) 290 830 >10000 SNRA 2-Chloro-PP (oCPP) 310 26 >3000 NRA 2-Bromo-PP (oBPP) 132 33 250 SNDRA 2-Nitro-PP (oNPP) 1870 770 >10000 SNRA 3-Chloro-PP (mCPP) 28–39 1400–>10000 >10000–63000 SRA 3-Fluoro-PP (mFPP) 115 340 2400 SNRA 3-Me-PP (mMPP) 110 >20000 >20000 SRA 3-OMe-PP (mMeOPP) 650 >10000 >10000 SRA 3-OH-PP (mOHPP) 230 174 2500 SNRA 3-TFM-PP (TFMPP) 121 >10000 >10000 SRA 4-Chloro-PP (pCPP) 4-Fluoro-PP (pFPP) 230 3200 >10000 SRA 4-Me-PP (pMPP) PAL-233 220 >10000 >20000 SRA 4-OMe-PP (pMeOPP) 3200 440–1500 6300–11000 SNDRA 4-TFM-PP (pTFMPP) 4-Ac-PP (pAcPP) 50 150 3000 SNRA 4-CN-PP (pCNPP) 36 6300 >10000 SRA 4-Phenyl-PP (pPhPP) >10000 1520 5200 NDRA 4-OH-PP (pOHPP) >10000 230 850 NDRA 4-Nitro-PP (pNPP) PAL-175 19–43 >10000 >10000 SRA 2,3-Dichloro-PP (2,3-DCPP) 10 36 108 SNDRA 2,3-DiMe-PP (2,3-DMPP) PAL-218 24–26 13.7–56 1207–1320 SNRA 2,4-Difluoro-PP (2,4-DFPP) 470 2300 >10000 SNRA 3,4-Dichloro-PP (3,4-DCPP) 3,4-Difluoro-PP (3,4-DFPP) 76 9200 >10000 SRA 3-TFM-4-Cl-PP (TFMCPP) PAL-179 33 >10000 >10000 SRA Notes: Assays were done using rat brain synaptosomes.
See also Substituted α-alkyltryptamine Substituted amphetamine Substituted cathinone Substituted methylenedioxyphenethylamine Substituted phenethylamine Substituted phenylmorpholine Substituted tryptamine
References
External links