An α2-AR antagonist and active metabolite of azapirones
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2-(1-Piperazinyl)pyrimidine

Item No. 34091

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
CAS Number
20980-22-7
Synonyms
  • PmP
  • 1-PP
  • 1-(2-Pyrimidyl)piperazine
Molecular Formula
C8H12N4
Formula Weight
164.2
Purity
≥98%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 10 mg/mlEthanol: 10 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
247 nm
SMILES
C1(N2CCNCC2)=NC=CC=N1
InChi Code
InChI=1S/C8H12N4/c1-2-10-8(11-3-1)12-6-4-9-5-7-12/h1-3,9H,4-7H2
InChi Key
MRBFGEHILMYPTF-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    10 g

    $40

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    25 g

    $65

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    Cayman Chemical
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    Product Description

    2-(1-Piperazinyl)pyrimidine is an antagonist of α2-adrenergic receptors (α2-ARs; pA2 = 6.8 in rat brain synaptosomes) and an active metabolite of various azapirones.1,2,3,4 It is an active metabolite of tandospirone (Item No. 40436), buspirone, ipsapirone (Item No. 39918 | 22075), and gepirone, among others. 2-(1-Piperazinyl)pyrimidine prevents clonidine-induced slowing of gastrointestinal transit in rats (ED50 = 0.8 mg/kg).2 It increases drinking in the Vogel punished drinking task, indicating anxiolytic-like activity, in rats when administered at doses ranging from 1 to 4 mg/kg.3 2-(1-Piperazinyl)pyrimidine (0.25-1 mg/kg) also reduces the amplitude of electrically stimulated excitatory post-synaptic potentials (EPSPs) in the hippocampal CA1 region in rats, an effect that can be blocked by the serotonin (5-HT) receptor subtype 5-HT1A antagonist spiroxatrine.4 It has also been used as a phosphopeptide derivatization agent.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Gobbi, M., Frittoli, E., and Mennini, T. Antagonist properties of 1-(2-pyrimidinyl)piperazine at presynaptic α2-adrenoceptors in the rat brain. Eur. J. Pharmacol. 180(1), 183-186 (1990).

    2. Bianchi, G., Caccia, S., Della Vedova, F., et al. The α2-adrenoceptor antagonist activity of ipsapirone and gepirone is mediated by their common metabolite 1-(2-pyrimidinyl)-piperazine (PmP). Eur. J. Pharmacol. 151(3), 365-371 (1988).

    3. Gower, A.J., and Tricklebank, M.D. α2-adrenoceptor antagonist activity may account for the effects of buspirone in an anticonflict test in the rat. Eur. J. Pharmacol. 155(1-2), 129-137 (1988).

    4. Manahan-Vaughan, D., Anwyl, R., and Rowan, M.J. The azapirone metabolite 1-(2-pyrimidinyl)piperazine depresses excitatory synaptic transmission in the hippocampus of the alert rat via 5-HT1A receptors. Eur. J. Pharmacol. 294(2-3), 617-624 (1995).

    5. Zhang, L., Xu, Y., Lu, H., et al. Carboxy group derivatization for enhanced electron-transfer dissociation mass spectrometric analysis of phosphopeptides. Proteomics 9(16), 4093-4097 (2009).