Substituted piperazine
Class of chemical compounds
From Wikipedia, the free encyclopedia
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
Chemical structures of selected benzylpiperazines
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
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.[3]
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]
- 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[4]
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.
By drug class
- Amoxapine
- Befuraline
- Buspirone
- Flesinoxan
- Gepirone
- Ipsapirone
- Nefazodone
- Piberaline
- Tandospirone
- Trazodone
- Vilazodone
- Vortioxetine
- Zalospirone
- 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)
Others
- 6-Nitroquipazine
- Antrafenine
- Diethylcarbamazine
- Diphenazine
- Fipexide
- Imatinib
- NSI-189
- Pipobroman (antineoplastic agent)
- Quipazine
- Sunifiram (nootropic)
- Tolpiprazole (tranquilizer)
Activities
| Compound | PAL # | Serotonin | Norepinephrine | Dopamine | Type | Ref | ||
|---|---|---|---|---|---|---|---|---|
| 1-Benzylpiperazine (BZP) | ND | 6050–>100000 | 62.2–68 | 175–600 | NDRA | [5][6][7][8][9][10] | ||
| 1-Phenylpiperazine (PP) | ND | 880 | 186 | 2530 | SNRA | [11] | ||
| 2-Me-PP (oMPP) | PAL-169 | 175 | 39.1 | 296–542 | SNDRA | [11][12][10] | ||
| 2-OMe-PP (oMeOPP) | ND | ND | ND | ND | ND | ND | ||
| 2-TFM-PP (oTFMPP) | ND | 570 | 350 | 11200 | SNRA | [11] | ||
| 2-SMe-PP (oMTPP) | ND | 270 | >10000 | >10000 | SRA | [11] | ||
| 2-Et-PP (oEtPP) | ND | 290 | 830 | >10000 | SNRA | [11] | ||
| 2-Chloro-PP (oCPP) | ND | 310 | 26 | >3000 | NRA | [11] | ||
| 2-Bromo-PP (oBPP) | ND | 132 | 33 | 250 | SNDRA | [11] | ||
| 2-Nitro-PP (oNPP) | ND | 1870 | 770 | >10000 | SNRA | [11] | ||
| 3-Chloro-PP (mCPP) | ND | 28–39 | 1400–>10000 | >10000–63000 | SRA | [6][13][14][15] | ||
| 3-Fluoro-PP (mFPP) | ND | 115 | 340 | 2400 | SNRA | [11] | ||
| 3-Me-PP (mMPP) | ND | 110 | >20000 | >20000 | SRA | [11] | ||
| 3-OMe-PP (mMeOPP) | ND | 650 | >10000 | >10000 | SRA | [11] | ||
| 3-OH-PP (mOHPP) | ND | 230 | 174 | 2500 | SNRA | [11] | ||
| 3-TFM-PP (TFMPP) | ND | 121 | >10000 | >10000 | SRA | [8][7][9] | ||
| 4-Chloro-PP (pCPP) | ND | ND | ND | ND | ND | ND | ||
| 4-Fluoro-PP (pFPP) | ND | 230 | 3200 | >10000 | SRA | [11] | ||
| 4-Me-PP (pMPP) | PAL-233 | 220 | >10000 | >20000 | SRA | [11][10] | ||
| 4-OMe-PP (pMeOPP) | ND | 3200 | 440–1500 | 6300–11000 | SNDRA | [11][6] | ||
| 4-TFM-PP (pTFMPP) | ND | ND | ND | ND | ND | ND | ||
| 4-Ac-PP (pAcPP) | ND | 50 | 150 | 3000 | SNRA | [11] | ||
| 4-CN-PP (pCNPP) | ND | 36 | 6300 | >10000 | SRA | [11] | ||
| 4-Phenyl-PP (pPhPP) | ND | >10000 | 1520 | 5200 | NDRA | [11] | ||
| 4-OH-PP (pOHPP) | ND | >10000 | 230 | 850 | NDRA | [11] | ||
| 4-Nitro-PP (pNPP) | PAL-175 | 19–43 | >10000 | >10000 | SRA | [11][4] | ||
| 2,3-Dichloro-PP (2,3-DCPP) | ND | 10 | 36 | 108 | SNDRA | [11] | ||
| 2,3-DiMe-PP (2,3-DMPP) | PAL-218 | 24–26 | 13.7–56 | 1207–1320 | SNRA | [11][4][10] | ||
| 2,4-Difluoro-PP (2,4-DFPP) | ND | 470 | 2300 | >10000 | SNRA | [11] | ||
| 3,4-Dichloro-PP (3,4-DCPP) | ND | ND | ND | ND | ND | ND | ||
| 3,4-Difluoro-PP (3,4-DFPP) | ND | 76 | 9200 | >10000 | SRA | [11] | ||
| 3-TFM-4-Cl-PP (TFMCPP) | PAL-179 | 33 | >10000 | >10000 | SRA | [4] | ||
| Notes: Assays were done using rat brain synaptosomes. | ||||||||