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 (MeOP, MEXP) ((4-methoxyphenyl)(4-methylpiperazin-1-yl)methanone)
*
Sunifiram (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, 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, 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 th ...
, 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 (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
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 ...
.
See also
*
Substituted α-alkyltryptamine
*
Substituted amphetamine
*
Substituted cathinone
Substituted cathinones, which include some stimulants and entactogens, are derivatives of cathinone. They feature a phenethylamine core with an alkyl group attached to the alpha carbon, and a ketone group attached to the beta carbon, along ...
*
Substituted methylenedioxyphenethylamine
Substitution reaction, Substituted methylenedioxy- phenethylamines (MDxx) are a large chemical class of derivative (chemistry), derivatives of the phenethylamines, which includes many psychoactive drugs that act as entactogens, psychedelic drug, ...
*
Substituted phenethylamine
Substituted phenethylamines (or simply phenethylamines) are a chemical class of organic compounds that are based upon the phenethylamine structure; the class is composed of all the derivative compounds of phenethylamine which can be formed by ...
*
Substituted phenylmorpholine
*
Substituted tryptamine
Substituted tryptamines, or serotonin analogues, are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all tryptamines contain an indole ring, joined to an amino group, amino (NH2) group ...
References
{{DEFAULTSORT:Substituted Piperazines
Chemical classes of psychoactive drugs
Designer drugs
Piperazines