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 (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 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 Structural analog, analog of methylbenzylpiperazine. Very little data exists ...

(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 anal ...

(1-benzoyl-4-propanoylpiperazine) * 3-Methylbenzylpiperazine (3-MeBZP) Befuraline, fipexide, and piberaline 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, ...

Phenylpiperazines

''ortho''-Substituted

* 2-Chlorophenylpiperazine (oCPP) * 2-Methylphenylpiperazine (oMPP) * 2-Methoxyphenylpiperazine (oMeOPP)

Enpiprazole Enpiprazole (INN, BAN) is an anxiolytic drug of the phenylpiperazine group that was never marketed. It produces anxiolytic-like effects in animals, though these effects appear to be biphasic and may reverse at high doses. It is known to produce ...

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 1-(3-Chlorophenyl)-4-(2-phenylethyl)piperazine (3C-PEP) is a designer drug of the piperazine class of chemical substances. 3C-PEP is related to ''meta''-cholorophenylpiperazine (mCPP) and phenethylamine that can be thought of as mCPP having a p ...

(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, f ...

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 the ...

, and others produce mCPP as a metabolite.

''para''-Substituted

* 4-Chlorophenylpiperazine (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 1-Phenylpiperazine is a simple chemical compound featuring a phenyl functional group, group bound to a piperazine functional group, ring. The suffix ‘-piprazole’ is sometimes used in the names of drugs to indicate they belong to this class. L ...

(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 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 b ...

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 developmen ...

, 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 li ...

produce 1-PP as a

References

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