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

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

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

Antianginals

Antidepressants

Antihistamines

Antiserotonergics

EGIS-7625

Antipsychotics

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

Others

Activities

Monoamine release (EC₅₀Tooltip half-maximal effective concentration, nM) of arylpiperazines
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.

References

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