1-(2-Pyrimidinyl)piperazine
Encyclopedia
1-piperazine (1-PP, 1-PmP) is a chemical compound
and piperazine
derivative. It is known to act as an α2-adrenergic receptor antagonist
, and as a 5-HT1A receptor
partial agonist
to a much lesser extent. It does not appear to have any significant affinity for the D2 or α1-adrenergic receptors.
A number of pyrimidinylpiperazine derivatives are drug
s, including:
The anxiolytic
s are also classified as azapirones due to the azaspirodecanedione moiety in their structures. 1-PP is a common metabolite
of most or all of the listed agents. Alnespirone
, binospirone
, and enilospirone
, despite being azapirones, are not piperazines and therefore do not metabolize to 1-PP, and while perospirone
and tiospirone
are piperazines, they are instead benzothiazole
-substituted piperazines and do not metabolize to 1-PP either.
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...
and piperazine
Piperazine
Piperazine is an organic compound that consists of a six-membered ring containing two opposing nitrogen atoms. Piperazine exists as small alkaline deliquescent crystals with a saline taste....
derivative. It is known to act as an α2-adrenergic receptor antagonist
Receptor antagonist
A receptor antagonist is a type of receptor ligand or drug that does not provoke a biological response itself upon binding to a receptor, but blocks or dampens agonist-mediated responses...
, and as a 5-HT1A receptor
5-HT1A receptor
The 5-HT1A receptor is a subtype of 5-HT receptor that binds the endogenous neurotransmitter serotonin . It is a G protein-coupled receptor that is coupled to Gi/Go and mediates inhibitory neurotransmission...
partial agonist
Partial agonist
Partial agonists bind and activate a given receptor, but have only partial efficacy at the receptor relative to a full agonist...
to a much lesser extent. It does not appear to have any significant affinity for the D2 or α1-adrenergic receptors.
A number of pyrimidinylpiperazine derivatives are drug
Drug
A drug, broadly speaking, is any substance that, when absorbed into the body of a living organism, alters normal bodily function. There is no single, precise definition, as there are different meanings in drug control law, government regulations, medicine, and colloquial usage.In pharmacology, a...
s, including:
- BuspironeBuspironeBuspirone is an anxiolytic psychoactive drug of the azapirone chemical class, and is primarily used to treat generalized anxiety disorder Bristol-Myers Squibb gained FDA approval of buspirone in 1986 for treatment of GAD...
- Anxiolytic - DasatinibDasatinibDasatinib, previously known as BMS-354825, is a cancer drug produced by Bristol-Myers Squibb and sold under the trade name Sprycel. Dasatinib is an oral multi- BCR/ABL and Src family tyrosine kinase inhibitor approved for use in patients with chronic myelogenous leukemia after imatinib treatment...
- Anticancer agent - EptapironeEptapironeEptapirone is a very potent and highly selective 5-HT1A receptor full agonist of the azapirone class. Its affinity for the 5-HT1A receptor is 4.8 nM or 8.33 , and its intrinsic activity is 100% or equal to that of serotonin....
- Anxiolytic - GepironeGepironeGepirone is a psychoactive drug and research chemical of the piperazine and azapirone chemical classes. It is currently under clinical development in an extended release form as an anxiolytic and antidepressant agent...
- Anxiolytic - IpsapironeIpsapironeIpsapirone is a selective 5-HT1A receptor partial agonist of the piperazine and azapirone chemical classes. It has antidepressant and anxiolytic effects.- References :...
- Anxiolytic - PiribedilPiribedilPiribedil is an antiparkinsonian agent and piperazine derivative which acts as a D2 and D3 receptor agonist...
- Antiparkinsonian agent - RevospironeRevospironeRevospirone is a selective 5-HT1A receptor partial agonist of the azapirone class. As with buspirone, gepirone, ipsapirone, and tandospirone, 1-PP is an active metabolite of revospirone; hence, it also has some α2-adrenergic receptor antagonist properties.- References :...
- Anxiolytic - TandospironeTandospironeTandospirone , also known as metanopirone, is an anxiolytic and antidepressant used in China and Japan, where it is marketed by Dainippon Sumitomo Pharma...
- Anxiolytic - TirilazadTirilazadTirilazad is a drug proposed for use in the treatment of stroke, though results so far have been mixed....
- Alpha blocker - UmespironeUmespironeUmespirone is a drug of the azapirone class which possesses anxiolytic and antipsychotic properties. It behaves as a 5-HT1A receptor partial agonist , D2 receptor partial agonist , and α1-adrenoceptor receptor antagonist , and also has weak affinity for the sigma receptor...
- Anxiolytic - ZalospironeZalospironeZalospirone is a selective 5-HT1A partial agonist of the azapirone chemical class. It was found to be effective in the treatment of anxiety and depression in clinical trials, but a high proportion of subjects dropped out due to side effects and development was subsequently never completed.-...
- Anxiolytic
The anxiolytic
Anxiolytic
An anxiolytic is a drug used for the treatment of anxiety, and its related psychological and physical symptoms...
s are also classified as azapirones due to the azaspirodecanedione moiety in their structures. 1-PP is a common metabolite
Metabolite
Metabolites are the intermediates and products of metabolism. The term metabolite is usually restricted to small molecules. A primary metabolite is directly involved in normal growth, development, and reproduction. Alcohol is an example of a primary metabolite produced in large-scale by industrial...
of most or all of the listed agents. Alnespirone
Alnespirone
Alnespirone is a selective 5-HT1A receptor full agonist of the azapirone chemical class. It has antidepressant and anxiolytic effects.- References :...
, binospirone
Binospirone
Binospirone is a drug which acts as a partial agonist at 5-HT1A somatodendritic autoreceptors but as an antagonist at postsynaptic 5-HT1A receptors. It has anxiolytic effects.- References :...
, and enilospirone
Enilospirone
Enilospirone is a selective 5-HT1A receptor agonist of the azapirone class....
, despite being azapirones, are not piperazines and therefore do not metabolize to 1-PP, and while perospirone
Perospirone
Perospirone is an atypical antipsychotic of the azapirone chemical class. It was introduced in Japan in 2001 by Dainippon Sumitomo Pharma for the treatment of schizophrenia and acute bipolar mania. Perospirone acts as a 5-HT1A receptor partial agonist, 5-HT2A receptor inverse agonist, and D2, D4,...
and tiospirone
Tiospirone
Tiospirone , also sometimes called tiaspirone or tiosperone, is an atypical antipsychotic drug of the azapirone class...
are piperazines, they are instead benzothiazole
Benzothiazole
Benzothiazole is an aromatic heterocyclic compound with the chemical formula . It is colorless, slightly viscous liquid. Although the parent compound, benzothiazole is not widely used, many of its derivatives are found in commercial products or in nature...
-substituted piperazines and do not metabolize to 1-PP either.
See also
- PyridinylpiperazinePyridinylpiperazine1-piperazine is a chemical compound and piperazine derivative. Some derivatives of this substance are known to act as potent and selective a2-adrenergic receptor antagonists, such as 1-piperazine....
- PhenylpiperazinePhenylpiperazine1-Phenylpiperazine is a simple chemical compound featuring a phenyl group bound to a piperazine ring. The suffix '-piprazole' is sometimes used in the names of drugs to indicate they belong to this class....
- DiphenylmethylpiperazineDiphenylmethylpiperazine1-piperazine, also known as benzhydrylpiperazine, is a chemical compound and piperazine derivative. It features a piperazine ring with a benzhydryl group bound to one of the nitrogens....
- BenzylpiperazineBenzylpiperazineBenzylpiperazine is a recreational drug with euphoric, 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, renal toxicity, and seizures...