Substituted piperazines are a class of

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

s based on a

piperazine Piperazine () is an organic compound that consists of a six-membered ring containing two nitrogen atoms at opposite positions in the ring. Piperazine exists as small alkaline deliquescent crystals with a saline taste. The piperazines are a broad ...

core. Some are used as

recreational drug Recreational drug use indicates the use of one or more psychoactive drugs to induce an altered state of consciousness either for pleasure or for some other casual purpose or pastime by modifying the perceptions and emotions of the user. When a ...

s and some are used in

scientific research The scientific method is an empirical method for acquiring knowledge that has characterized the development of science since at least the 17th century (with notable practitioners in previous centuries; see the article history of scientific m ...

List of substituted piperazines

Benzylpiperazines

File:Benzylpiperazine.svg, 1-Benzylpiperazine File:MBZP.svg, 1-Methyl-4-benzylpiperazine File:DBZP.svg, 1,4-Dibenzylpiperazine File:MDBZP.svg, 3,4-Methylenedioxy-1-benzylpiperazine File:2C-B-BZP.svg, 4-Bromo-2,5-dimethoxy-1-benzylpiperazine File:Methoxypiperamide.png, Methoxypiperamide File:Sunifiram.svg , Sunifiram File:3-Methylbenzylpiperazine structure.png, 3-Methylbenzylpiperazine *

1-Benzylpiperazine Benzylpiperazine (BZP) is a recreational drug with euphoriant and stimulant properties. The effects produced by BZP are comparable to those produced by amphetamine. Adverse effects have been reported following its use including acute psychosis, ...

(BZP) *

1-Methyl-4-benzylpiperazine Methylbenzylpiperazine (1-methyl-4-benzylpiperazine, MBZP) is a stimulant drug which is a derivative of benzylpiperazine. MBZP has been sold as an ingredient in legal recreational drugs known as "party pills", initially in New Zealand and subsequ ...

(MBZP) *

1,4-Dibenzylpiperazine Dibenzylpiperazine (DBZP) is a piperazine derivative often found as an impurity in the recreational stimulant drug benzylpiperazine (BZP). Presence of DBZP is a marker for low quality or badly made BZP. It can be made as a reaction byproduct duri ...

(DBZP) *

3,4-Methylenedioxy-1-benzylpiperazine 1-(3,4-Methylenedioxybenzyl)piperazine (MDBZP, piperonylpiperazine) is a chemical compound of the piperazine chemical class related to benzylpiperazine (BZP). MDBZP has been sold as a designer drug and has even been found as an ingredient in stre ...

(MDBZP) *

4-Bromo-2,5-dimethoxy-1-benzylpiperazine 4-Bromo-2,5-dimethoxy-1-benzylpiperazine (2C-B-BZP) is a psychoactive drug and research chemical of the piperazine chemical class which has been sold as a "designer drug". It produces stimulant effects similar to those of benzylpiperazine (BZP). ...

(2C-B-BZP) *

Methoxypiperamide Methoxypiperamide (also known as MeOP and MEXP) is a psychoactive drug of the piperazine class that has been sold online as a designer drug. It is the 4-methoxy-α-keto analog of methylbenzylpiperazine. Very little data exists about the pharmaco ...

(MeOP, MEXP) ((4-methoxyphenyl)(4-methylpiperazin-1-yl)methanone) *

Sunifiram Sunifiram (developmental code name DM-235) is an experimental drug which has antiamnesic effects in animal studies and with significantly higher potency than piracetam. Sunifiram is a molecular simplification of unifiram (DM-232). Another analo ...

(1-benzoyl-4-propanoylpiperazine) *

3-Methylbenzylpiperazine 3-Methylbenzylpiperazine (3-Me-BZP) is a stimulant drug which is a derivative of benzylpiperazine. It has been sold as a designer drug, first being identified in Sweden in February 2012. See also * Methylbenzylpiperazine * Substituted piperaz ...

(3-MeBZP)

Befuraline Befuraline (DIV-154) is a psychoactive drug and member of the piperazine chemical class which was developed in Germany in the 1970s. Befuraline has stimulant and antidepressant effects and has seen some use in Germany and France, although it has ...

fipexide Fipexide (Attentil, Vigilor) is a psychoactive drug of the piperazine chemical class which was developed in Italy in 1983. It was used as a nootropic drug in Italy and France, mainly for the treatment of senile dementia, but is no longer in commo ...

, and

piberaline Piberaline (EGYT-475; Trelibet) is a psychoactive drug and member of the piperazine chemical class which was developed in the 1980s. It has stimulant and antidepressant effects which are thought to be due largely to its active metabolite benzylp ...

produce benzylpiperazine as a

metabolite In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, c ...

Phenylpiperazines

''ortho''-Substituted

* 2-Chlorophenylpiperazine (oCPP) * 2-Methylphenylpiperazine (oMPP) * 2-Methoxyphenylpiperazine (oMeOPP) Enpiprazole is known to produce oCPP as a metabolite.

Enciprazine Enciprazine ( INN, BAN; enciprazine hydrochloride (USAN); developmental code names WY-48624, D-3112), is an anxiolytic and antipsychotic of the phenylpiperazine class which was never marketed. It shows high affinity for the α1-adrenergic rece ...

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 Trazodone, sold under many brand names, is an antidepressant medication. It is used to treat major depressive disorder, anxiety disorders, and difficulties with sleep. The medication is taken orally. Common side-effects include dry mouth, fe ...

nefazodone Nefazodone, sold formerly under the brand names Serzone, Dutonin, and Nefadar among others, is an atypical antidepressant which was first marketed by Bristol-Myers Squibb (BMS) in 1994 but has since largely been discontinued. BMS withdrew it from ...

mepiprazole Mepiprazole (INN, BAN) (brand name Psigodal) is an anxiolytic drug of the phenylpiperazine group with additional antidepressant properties that is marketed in Spain. It acts as a 5-HT2A and α1-adrenergic receptor antagonist and inhibits th ...

, and others produce mCPP as a metabolite.

''para''-Substituted

4-Chlorophenylpiperazine ''para''-Chlorophenylpiperazine (pCPP) is a psychoactive drug of the phenylpiperazine class. It is relatively obscure, with limited human use, and produces slightly psychedelic effects. It has been encountered in illicit capsules as a recreationa ...

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

Multiple substitutions

* 2,3-Dichlorophenylpiperazine (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 ORG-12962 is a pyridinylpiperazine drug developed by Organon, which acts as a potent and selective agonist for the 5-HT2 receptor family, with highest affinity at 5-HT2C and lowest at 5-HT2B subtypes. It was developed as a potential anti-a ...

(1-(5-trifluoromethyl-6-chloropyridin-2-yl)piperazine) *

Quipazine Quipazine is a serotonergic drug of the piperazine group which is used in scientific research. It was originally intended as an antidepressant but never developed for medical use. Pharmacology Pharmacodynamics Quipazine is a serotonin reuptake ...

(2-piperazin-1-ylquinoline) Many

azapirone Azapirones are a class of drugs used as anxiolytics, antidepressants, and antipsychotics. They are commonly used as add-ons to other antidepressants, such as selective serotonin reuptake inhibitors (SSRIs). Medical uses Azapirones have shown ...

s such as

buspirone Buspirone, sold under the brand name Buspar, among others, is a medication primarily used to treat anxiety disorders, particularly generalized anxiety disorder. Benefits support its short-term use. It is taken by mouth, and it may take up to fo ...

gepirone Gepirone is an antidepressant and anxiolytic drug of the azapirone group that was synthesized by Bristol-Myers Squibb in 1986 and has been under development for the treatment of depression but has yet to be marketed. It has been under developm ...

, and

tandospirone Tandospirone (brand name Sediel) is an anxiolytic and antidepressant drug used in China and Japan, where it is marketed by Dainippon Sumitomo Pharma. It is a member of the azapirone class of drugs and is closely related to other azapirones l ...

produce 1-PP as a

References

{{DEFAULTSORT:Substituted Piperazines Chemical classes of psychoactive drugs Designer drugs Piperazines