Pyrimidinylpiperazine
Chemical compound
From Wikipedia, the free encyclopedia
1-(2-Pyrimidinyl)piperazine (1-PP, 1-PmP) is a chemical compound and piperazine derivative. It is known to act as an antagonist of the α2-adrenergic receptor (Ki = 7.3–40 nM)[1] and, to a much lesser extent, as a partial agonist of the 5-HT1A receptor (Ki = 414 nM; Emax = 54%).[2][3] It has negligible affinity for the dopamine D2, D3, and D4 receptors (Ki > 10,000 nM) and does not appear to have significant affinity for the α1-adrenergic receptors.[4][additional citation(s) needed] Its crystal structure has been determined.[5]
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| Names | |
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| Preferred IUPAC name
2-(Piperazin-1-yl)pyrimidine | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.040.107 |
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PubChem CID |
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| UNII | |
CompTox Dashboard (EPA) |
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| Properties | |
| C8H12N4 | |
| Molar mass | 164.21 g/mol |
| Hazards | |
| GHS labelling: | |
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| Danger | |
| H314, H315, H319, H335 | |
| P260, P264, P271, P280, P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P305+P351+P338, P310, P312, P321, P332+P313, P337+P313, P362, P363, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Derivatives
A number of pyrimidinylpiperazine derivatives are drugs, including:
- Buspirone – anxiolytic
- Dasatinib – anticancer agent
- Eptapirone – anxiolytic
- Gepirone – anxiolytic
- Ipsapirone – anxiolytic
- Piribedil – antiparkinsonian agent
- Revospirone – anxiolytic
- Tandospirone – anxiolytic
- Tirilazad – neuroprotective agent
- Umespirone – anxiolytic
- Zalospirone – anxiolytic
The anxiolytics 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.[1][6] 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.