Pyrimidinylpiperazine
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| Names | |
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| IUPAC name
2-(piperazin-1-yl)pyrimidine
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| Identifiers | |
| 3D model (Jmol) | Interactive image |
| ChEMBL | ChEMBL724  Y |
| ChemSpider | 80080 Y |
| PubChem | 88747 |
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| Properties | |
| C8H12N4 | |
| Molar mass | 164.21 g/mol |
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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| Infobox references | |
1-(2-Pyrimidinyl)piperazine (1-PP, 1-PmP) is a chemical compound and piperazine derivative. It is known to act as an α2-adrenergic receptor antagonist,[1] and as a 5-HT1A receptor partial agonist to a much lesser extent.[2] It does not appear to have any significant affinity for the D2 or α1-adrenergic receptors.
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][3] 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.
See also[edit]
References[edit]
- ^ a b Blier; Curet, O.; Chaput, Y.; De Montigny, C. (1991). "Tandospirone and its metabolite, 1-(2-pyrimidinyl)-piperazine--II. Effects of acute administration of 1-PP and long-term administration of tandospirone on noradrenergic neurotransmission". Neuropharmacology. 30 (7): 691–701. doi:10.1016/0028-3908(91)90176-C. PMID 1681447.
- ^ Zuideveld, K. P. (December 2002). "Pharmacokinetic-pharmacodynamic modeling of buspirone and its metabolite 1-(2-pyrimidinyl)-piperazine in rats". J. Pharmacol. Exp. Ther. 303 (3): 1130–1137. doi:10.1124/jpet.102.036798. PMID 12438536.
- ^ Astier, B.; Lambás Señas, L.; Soulière, F.; Schmitt, P.; Urbain, N.; Rentero, N.; Bert, L.; Denoroy, L.; Renaud, B.; Lesourd, M.; Muñoz; Chouvet, G. (2003). "In vivo comparison of two 5-HT1A receptors agonists alnespirone (S-20499) and buspirone on locus coeruleus neuronal activity". European Journal of Pharmacology. 459 (1): 17–26. doi:10.1016/S0014-2999(02)02814-5. PMID 12505530.
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| Simple piperazines (no additional rings) |
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|---|---|
| Phenylpiperazines |
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| Benzylpiperazines | |
| Diphenylalkylpiperazines (benzhydrylalkylpiperazines) |
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| Pyrimidinylpiperazines |
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| Pyridinylpiperazines | |
| Benzo(iso)thiazolylpiperazines | |
| Tricyclics (piperazine attached via side chain) |
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| Others/Uncategorized | |
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