Pyrimidinylpiperazine

Pyrimidinylpiperazine
Names
	Preferred IUPAC name 2-(Piperazin-1-yl)pyrimidine
Identifiers
CAS Number	20980-22-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:166562;
ChEMBL	ChEMBL724 ;
ChemSpider	80080 ;
ECHA InfoCard	100.040.107
EC Number	244-135-5;
PubChem CID	88747;
UNII	H3B5B38F56;
CompTox Dashboard (EPA)	DTXSID00864967 ;
	InChI InChI=1S/C8H12N4/c1-2-10-8(11-3-1)12-6-4-9-5-7-12/h1-3,9H,4-7H2 Key: MRBFGEHILMYPTF-UHFFFAOYSA-N ; InChI=1S/C8H12N4/c1-2-10-8(11-3-1)12-6-4-9-5-7-12/h1-3,9H,4-7H2; InChI=1S/C8H12N4/c1-2-10-8(11-3-1)12-6-4-9-5-7-12/h1-3,9H,4-7H2 Key: MRBFGEHILMYPTF-UHFFFAOYSA-N;
	SMILES n1cccnc1N2CCNCC2;
Properties
Chemical formula	C8H12N4
Molar mass	164.21 g/mol
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H314, H315, H319, H335
Precautionary statements	P260, P261, 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). verify (what is ?) 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 (K_i = 7.3–40 nM)^[1] and, to a much lesser extent, as a partial agonist of the 5-HT_1A receptor (K_i = 414 nM; E_max = 54%).^[2]^[3] It has negligible affinity for the dopamine D₂, D₃, and D₄ receptors (K_i > 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]

^ Blier P, 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. S2CID 44297577.
^ Zuideveld KP, Rusiç-Pavletiç J, Maas HJ, Peletier LA, Van der Graaf PH, Danhof M (2002). "Pharmacokinetic-pharmacodynamic modeling of buspirone and its metabolite 1-(2-pyrimidinyl)-piperazine in rats". J. Pharmacol. Exp. Ther. 303 (3): 1130–7. doi:10.1124/jpet.102.036798. PMID 12438536. S2CID 14139919.
^ Gobert A, Newman-Tancredi A, Rivet J, Audinot V, Millan M (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. S2CID 54355225.
^ Bergman J, Roof RA, Furman CA, Conroy JL, Mello NK, Sibley DR, Skolnick P (2013). "Modification of cocaine self-administration by buspirone (buspar®): potential involvement of D3 and D4 dopamine receptors". Int. J. Neuropsychopharmacol. 16 (2): 445–58. doi:10.1017/S1461145712000661. PMC 5100812. PMID 22827916.
^ Yamuna TS, Jasinski JP, Kaur M, Anderson BJ, Yathirajan HS (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. Bibcode:2014AcCrE..70..203Y. doi:10.1107/S1600536814020169. PMC 4257175. PMID 25484652.

[pmid1681447-1] Blier P, 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. S2CID 44297577.

[pmid12438536-2] Zuideveld KP, Rusiç-Pavletiç J, Maas HJ, Peletier LA, Van der Graaf PH, Danhof M (2002). "Pharmacokinetic-pharmacodynamic modeling of buspirone and its metabolite 1-(2-pyrimidinyl)-piperazine in rats". J. Pharmacol. Exp. Ther. 303 (3): 1130–7. doi:10.1124/jpet.102.036798. PMID 12438536. S2CID 14139919.

[GobertNewman-Tancredi1997-3] Gobert A, Newman-Tancredi A, Rivet J, Audinot V, Millan M (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. S2CID 54355225.

[pmid22827916-4] Bergman J, Roof RA, Furman CA, Conroy JL, Mello NK, Sibley DR, Skolnick P (2013). "Modification of cocaine self-administration by buspirone (buspar®): potential involvement of D3 and D4 dopamine receptors". Int. J. Neuropsychopharmacol. 16 (2): 445–58. doi:10.1017/S1461145712000661. PMC 5100812. PMID 22827916.

[5] Yamuna TS, Jasinski JP, Kaur M, Anderson BJ, Yathirajan HS (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. Bibcode:2014AcCrE..70..203Y. doi:10.1107/S1600536814020169. PMC 4257175. PMID 25484652.

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