Pyrimidinylpiperazine
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| Pyrimidinylpiperazine | |
|---|---|
| File:Pyrimidinylpiperazine.png | |
| 2-(piperazin-1-yl)pyrimidine | |
| style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers | |
| PubChem | 88747 |
| ChemSpider | 80080 |
| SMILES | Script error: No such module "collapsible list". |
| InChI | Script error: No such module "collapsible list". |
| style="background: #F8EABA; text-align: center;" colspan="2" | Properties | |
| Molecular formula | C8H12N4 |
| Molar mass | 164.21 g/mol |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| 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 - Alpha blocker
- 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
References
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| Simple piperazines (no additional rings) | |
|---|---|
| Phenylpiperazines | Acaprazine • Antrafenine • Aripiprazole • Batoprazine • Bifeprunox • BRL-15,572 • Ciprofloxacin • CSP-2503 • Dapiprazole • DCPP • DMPP • Dropropizine • EGIS-12,233 • Elopiprazole • Eltoprazine • Enpiprazole • Ensaculin • Etoperidone • Flesinoxan • Flibanserin • Fluprazine • Itraconazole • Ketoconazole • Levodropropizine • Lorpiprazole • mCPP • MeOPP • Mepiprazole • Naftopidil • Naphthylpiperazine • Nefazodone • Niaprazine • Oxypertine • Pardoprunox • pCPP • pFPP • Posaconazole • PRX-00023 • S-14,506 • S-14,671 • S-15,535 • SB-258,585 • SB-271,046 • SB-357,134 • SB-399,885 • Sonepiprazole • TFMPP • Tolpiprazole • Trazodone • Urapidil • Vesnarinone • Vilazodone • WAY-100,135 • WAY-100,635 |
| Benzylpiperazines | 2C-B-BZP • Befuraline • Bifeprunox • Buclizine • BZP • Chlorbenzoxamine • DBZP • Fipexide • Imatinib • MBZP • MDBZP • Meclozine • Piberaline • Piribedil • Trimetazidine • Vesnarinone |
| Diphenylalkylpiperazines (benzhydrylalkylpiperazines) | Almitrine • Amperozide • BRL-15,572 • Buclizine • BW373U86 • Cetirizine • Chlorbenzoxamine • Chlorcyclizine • Cinnarizine • Clocinizine • Cyclizine • DBL-583 • Diphenylmethylpiperazine • Dotarizine • DPI-221 • DPI-287 • DPI-3290 • GBR-12,783 • GBR-12,935 • GBR-13,069 • GBR-13,098 • GBR-13,119 • Hydroxyzine • Lidoflazine • Manidipine • Meclozine • Oxatomide • SNC-80 • Vanoxerine |
| Pyrimidinylpiperazines | Buspirone • Dasatinib • Eptapirone • Gepirone • Ipsapirone • Piribedil • Pyrimidinylpiperazine • Revospirone • Tandospirone • Tirilazad • Trimazosin • Umespirone • Zalospirone |
| Pyridinylpiperazines | |
| Benzo(iso)thiazolylpiperazines | |
| Tricyclics (piperazine attached via side chain) | |
| Others | 6-Nitroquipazine • Azimilide • Cinepazet • Cyclohexylpiperazine • Hexocyclium • Indinavir • JNJ-7777120 • Lodenafil • Mirodenafil • PB-28 • Quipazine • Ranolazine • SA-4503 • Sildenafil • Tadalafil • Vardenafil • VUF-6002 • Zipeprol |
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- ↑ 1.0 1.1 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. edit
- ↑ Zuideveld, K. P.; Rusic-pavletic, J.; Maas, H. J.; Peletier, L. A.; Van Der Graaf, P. H.; Danhof, M. (2002). "Pharmacokinetic-pharmacodynamic modeling of buspirone and its metabolite 1-(2-pyrimidinyl)-piperazine in rats". The Journal of pharmacology and experimental therapeutics. 303 (3): 1130–1137. doi:10.1124/jpet.102.036798. PMID 12438536. More than one of
|author2=and|last2=specified (help); More than one of|author3=and|last3=specified (help); More than one of|author4=and|last4=specified (help); More than one of|author5=and|last5=specified (help); More than one of|author6=and|last6=specified (help) edit - ↑ Astier; Lambás Señas, L; Soulière, F; Schmitt, P; Urbain, N; Rentero, N; Bert, L; Denoroy, L; Renaud, B (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. edit
