Chemistry:Pyrimidinylpiperazine

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Short description: Chemical compound
Pyrimidinylpiperazine
Pyrimidinylpiperazine.png
Names
Preferred IUPAC name
2-(Piperazin-1-yl)pyrimidine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
EC Number
  • 244-135-5
UNII
Properties
C8H12N4
Molar mass 164.21 g/mol
Hazards
GHS pictograms GHS05: CorrosiveGHS07: Harmful
GHS Signal word Danger
H314, H315, H319, H335
P260, P261, P264, P271, P280, P301+330+331, P302+352, P303+361+353, P304+340, P305+351+338, P310, P312, P321, P332+313, P337+313, P362, P363, P403+233, 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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Infobox references

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]

Derivatives

A number of pyrimidinylpiperazine derivatives are drugs, including:

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.

See also

References

  1. ↑ 1.0 1.1 "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. 1991. doi:10.1016/0028-3908(91)90176-c. PMID 1681447. 
  2. ↑ "Pharmacokinetic-pharmacodynamic modeling of buspirone and its metabolite 1-(2-pyrimidinyl)-piperazine in rats". J. Pharmacol. Exp. Ther. 303 (3): 1130–7. 2002. doi:10.1124/jpet.102.036798. PMID 12438536. 
  3. ↑ Gobert, A.; Newman-Tancredi, A.; Rivet, J.M.; Audinot, V.; Millan, M.J. (1997). "P.1.047 Yohimbine is a potent, partial agonist at rat and cloned, human serotonin1A receptors: A comparison to buspirone and its metabolite, 1-pyrimidinylpiperazine". European Neuropsychopharmacology 7: S149–S150. doi:10.1016/S0924-977X(97)88496-9. ISSN 0924-977X. 
  4. ↑ "Modification of cocaine self-administration by buspirone (buspar®): potential involvement of D3 and D4 dopamine receptors". Int. J. Neuropsychopharmacol. 16 (2): 445–58. 2013. doi:10.1017/S1461145712000661. PMID 22827916. 
  5. ↑ Yamuna, T. S.; Jasinski, J. P.; Kaur, M.; Anderson, B. J.; Yathirajan, H. S. (1 October 2014). "Crystal structures of 4-(pyrimidin-2-yl)piperazin-1-ium chloride and 4-(pyrimidin-2-yl)piperazin-1-ium nitrate". Acta Crystallographica Section E: Structure Reports Online 70 (10): 203–206. doi:10.1107/S1600536814020169. PMID 25484652. 
  6. ↑ "In vivo comparison of two 5-HT1A receptors agonists alnespirone (S-20499) and buspirone on locus coeruleus neuronal activity". Eur. J. Pharmacol. 459 (1): 17–26. 2003. doi:10.1016/s0014-2999(02)02814-5. PMID 12505530. 




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