1-(2-Pyrimidinyl)piperazine (1-PP, 1-PmP) is a

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 ...

and

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 ...

derivative In mathematics, the derivative of a function of a real variable measures the sensitivity to change of the function value (output value) with respect to a change in its argument (input value). Derivatives are a fundamental tool of calculus. F ...

. It is known to act as an

antagonist An antagonist is a character in a story who is presented as the chief foe of the protagonist. Etymology The English word antagonist comes from the Greek ἀνταγωνιστής – ''antagonistēs'', "opponent, competitor, villain, enemy, riv ...

of the α₂-adrenergic receptor (K_i = 7.3–40 nM) and, to a much lesser extent, as a

partial agonist In pharmacology, partial agonists are drugs that bind to and activate a given receptor, but have only partial efficacy at the receptor relative to a full agonist. They may also be considered ligands which display both agonistic and antagonistic e ...

of the 5-HT_1A receptor (K_i = 414 nM; E_max = 54%). It has negligible

affinity Affinity may refer to: Commerce, finance and law * Affinity (law), kinship by marriage * Affinity analysis, a market research and business management technique * Affinity Credit Union, a Saskatchewan-based credit union * Affinity Equity Par ...

for the

dopamine Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic compound, organic chemical of the catecholamine and phenethylamine families. Dopamine const ...

D₂, D₃, and D₄ receptors (K_i > 10,000 nM) and does not appear to have significant affinity for the α₁-adrenergic receptors. Its crystal structure has been determined.

Derivatives

A number of pyrimidinylpiperazine derivatives are

drug A drug is any chemical substance that causes a change in an organism's physiology or psychology when consumed. Drugs are typically distinguished from food and substances that provide nutritional support. Consumption of drugs can be via insuffla ...

s, including: *

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 ...

anxiolytic An anxiolytic (; also antipanic or antianxiety agent) is a medication or other intervention that reduces anxiety. This effect is in contrast to anxiogenic agents which increase anxiety. Anxiolytic medications are used for the treatment of anxi ...

Dasatinib Dasatinib, sold under the brand name Sprycel among others, is a targeted therapy medication used to treat certain cases of chronic myelogenous leukemia (CML) and acute lymphoblastic leukemia (ALL). Specifically it is used to treat cases that ar ...

- anticancer agent *

Eptapirone Eptapirone (F-11,440) is a very potent and highly selective 5-HT1A receptor full agonist of the azapirone family. Its affinity for the 5-HT1A receptor was reported to be 4.8 nM (Ki) (or 8.33 (pKi)), and its intrinsic activity approximately equ ...

- anxiolytic *

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 ...

- anxiolytic *

Ipsapirone Ipsapirone is a selective 5-HT1A receptor partial agonist of the piperazine and azapirone chemical classes. It has antidepressant and anxiolytic effects. Ipsapirone was studied in several placebo-controlled trials for depression and continues ...

- anxiolytic *

Piribedil Piribedil (trade names Pronoran, Trivastal Retard, Trastal, Trivastan, Clarium and others) is an antiparkinsonian agent and piperazine derivative which acts as a D2 and D3 receptor agonist. It also has α2-adrenergic antagonist properties. ...

- antiparkinsonian agent *

Revospirone Revospirone (Bay Vq 7813) is an azapirone drug which was patented as a veterinary tranquilizer but was never marketed. It acts as a selective 5-HT1A receptor partial agonist. Similarly to other azapirones such as buspirone, revospirone produces ...

- anxiolytic *

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 ...

- anxiolytic *

Tirilazad Tirilazad is a drug that has been proposed to treat acute ischaemic stroke A stroke is a medical condition in which poor blood flow to the brain causes cell death. There are two main types of stroke: ischemic, due to lack of blood flow, and ...

- neuroprotective agent *

Umespirone Umespirone (KC-9172) is a drug of the azapirone class which possesses anxiolytic and antipsychotic properties. It behaves as a 5-HT1A receptor partial agonist (Ki = 15 nM), D2 receptor partial agonist (Ki = 23 nM), and α1-adrenoceptor recepto ...

- anxiolytic *

Zalospirone Zalospirone (WY-47,846) is a binding selectivity, selective 5-HT1A receptor, 5-HT1A partial agonist of the azapirone chemical class. It was found to be effective in the treatment of anxiety and major depressive disorder, depression in clinical tr ...

- anxiolytic The

s are also classified as

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 due to the

azaspirodecanedione Azaspirodecanedione is a chemical compound. It is a component of the chemical structures of several of the azapirones. See also * Azapirone * Azaspirodecane * Glutarimide * Ketone In organic chemistry, a ketone is a functional group wi ...

moiety in their structures. 1-PP is a common

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 ...

of most or all of the listed agents.

Alnespirone Alnespirone (S-20,499) is a selective 5-HT1A receptor full agonist of the azapirone chemical class. It has antidepressant and anxiolytic effects. See also * 8-OH-DPAT * Azapirone Azapirones are a class of drugs used as anxiolytics, anti ...

binospirone Binospirone (MDL-73,005-EF) 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. See also * Azapirone Azapirones are a class of ...

, and

enilospirone Enilospirone (CERM-3,726) is a selective 5-HT1A receptor agonist of the azapirone class. See also * Azapirone Azapirones are a class of drugs used as anxiolytics, antidepressants, and antipsychotics. They are commonly used as add-ons to ...

, despite being azapirones, are not piperazines and therefore do not metabolize to 1-PP, and while

perospirone Perospirone (Lullan) is an atypical antipsychotic of the azapirone family. It was introduced in Japan by Dainippon Sumitomo Pharma in 2001 for the treatment of schizophrenia and acute cases of bipolar mania. Medical uses Its primary uses are in ...

and tiospirone are piperazines, they are instead

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 ...

-substituted piperazines and do not metabolize to 1-PP either.

References

5-HT1A agonists Alpha-2 blockers Human drug metabolites Piperazines Aminopyrimidines Guanidines {{Nervous-system-drug-stub