A polyamine metabolite
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Agmatine (sulfate)

Item No. 23513

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-(4-aminobutyl)-guanidine, monosulfate
CAS Number
2482-00-0
Molecular Formula
C5H14N4 • H2SO4
Formula Weight
228.3
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 10 mg/ml
SMILES
NC(NCCCCN)=N.O=S(O)(O)=O
InChi Code
InChI=1S/C5H14N4.H2O4S/c6-3-1-2-4-9-5(7)8;1-5(2,3)4/h1-4,6H2,(H4,7,8,9);(H2,1,2,3,4)
InChi Key
PTAYFGHRDOMJGC-UHFFFAOYSA-N
Shipping & Storage Information
Storage
4°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 g

    $75

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    5 g

    $278

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    10 g

    $516

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    Product Description

    Agmatine is a metabolite formed during polyamine biosynthesis with diverse biological activities.1 Agmatine is released from and taken up by synaptosomes, demonstrating neurotransmitter-like activity. It binds to human adrenergic receptors (ARs) and imidazoline (I) receptors (Kis = 46.98, 164.4, 26.3, and 74.4 μM for α2A-, α2B-, and α2c-ARs and I2b, respectively).2 Agmatine acts as an antagonist of the NMDA receptor (NMDAR) in a voltage- and concentration-dependent manner in primary rat hippocampal neurons and antagonizes nicotinic acetylcholine receptors (nAChRs) in intact chick retina at 1 mM.3,4 It is an antagonist of the serotonin (5-HT) receptor subtype 5-HT3 in mouse N1E-115 neuroblastoma cells (IC50 = 141 μM) and blocks ATP-sensitive potassium channels (KATP) in a concentration-dependent manner in mouse islets of Langerhans β-cells.5,6 Agmatine competitively inhibits neuronal, macrophage, endothelial, and inducible nitric oxide synthase (NOS; Kis = 660, 220, 7,500, and 260 μM, respectively) and irreversibly inactivates neuronal NOS in the presence of calmodulin (Ki = 29 μM).7 In vivo, agmatine (10 mg/kg) lowers the ED50 value by 5.2- and 4.7-fold for morphine (Item No. ISO60147) and [D-Pen2,D-Pen5]enkephalin (DPDPE), respectively, in mice in a tail flick assay.8 It increases the nephron filtration rate when microperfused into the urinary space of rats, an effect that is reversed by the non-selective NOS inhibitor L-NG-monomethyl arginine (L-NMMA; Item Nos. 80200, 10005031).9

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Reis, D.J., and Regunathan, S. Is agmatine a novel neurotransmitter in brain? Trends Pharmacol. Sci. 21(5), 187-193 (2000).

    2. Piletz, J.E. Comparison of the properties of agmatine and endogenous clonidine-displacing substance at imidazoline and α-2 adrenergic receptors. J. Pharmacol. Exp. Ther. 272(2), 581-587 (1995).

    3. Yang, X.C., and Reis, D.J. Agmatine selectively blocks the N-methyl-D-aspartate subclass of glutamate receptor channels in rat hippocampal neurons. J. Pharmacol. Exp. Ther. 288(2), 544-549 (1999).

    4. Loring, R.H. Agmatine acts as an antagonist of neuronal nicotinic receptors. Br. J. Pharmacol. 99(1), 207-211 (1990).

    5. Molderings, G.J., Schmidt, K., Bönisch, H., et al. Inhibition of 5-HT3 receptor function by imidazolines in mouse neuroblastoma cells: potential involvement of σ2 binding sites. Naunyn Schmiedebergs Arch. Pharmacol. 345(3), 245-252 (1996).

    6. Shepherd, R.M., Hashmi, M.N., Kane, C., et al. Elevation of cytosolic calcium by imidazolines in mouse islets of Langerhans: Implications for stimulus-response coupling of insulin release. Br. J. Pharmacol. 119(5), 911-916 (1996).

    7. Demady, D.R., Jianmongkol, S., Vuletich, J.L., et al. Agmatine enhances the NADPH oxidase activity of neuronal NO synthase and leads to oxidative inactivation of the enzyme. Mol. Pharmacol. 59(1), 24-29 (2001).

    8. Kolesnikov, Y., Jain, S., and Pasternak, G.W. Modulation of opioid analgesia by agmatine. Eur. J. Pharmacol. 296(1), 17-22 (1996).

    9. Schwartz, D., Peterson, O.W., Mendonca, M., et al. Agmatine affects glomerular filtration via a nitric oxide synthase-dependent mechanism. Am. J. Physiol. 272(5 Pt 2), F597-F601 (1997).