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1,1-Dimethylbiguanide, Hydrochloride (CAS 1115-70-4)

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Synonym:Metformin hydrochloride
Application:A antihyperglycemic biguanide which stimulates AMPK
CAS Number:1115-70-4
Purity:≥99%
Molecular Weight:165.62
Molecular Formula:C4H11N5•HCl
Refer to Certificate of Analysis for lot specific data (including water content).
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Product NameCatalog #UnitPriceQtyAddFavorites
1,1-Dimethylbiguanide, Hydrochloride sc-202000 1 g $20
1,1-Dimethylbiguanide, Hydrochloride sc-202000A 5 g $31
Description
1,1-Dimethylbiguanide, Hydrochloride (Metformin) is a biguanide antihyperglycemic agent. Through glucose clamp investigation in rats 1,1-Dimethylbiguanide, Hydrochloride has been shown to lower blood glucose levels through improved glucose tolerance without stimulating insulin secretion, promoting weight gain or causing hypoglycemia. The biguanide reduces the diabetic complications on the cardiovascular system and increases insulin sensitivity. The compound has been shown not to change the synthesis of either GLUT4 or GLUT1 but does stimulate the transport of GLUT1 to the plasma membrane as seen in skeletal muscles. The compound has also been observed to improve peripheral arterials through selective reduction of PAI-1 (plasminogen activator inhibitor). In Xenopus oocytes the compound has been documented to act by increasing intercellular calcium concentration in addition to elevating receptor tyrosine kinase activity and inositol 1,4,5-trisphosphate. 1,1-Dimethylbiguanide, Hydrochloride has demonstrated the ability to induce fatty acid oxidation and to stimulate AMP-activated protein kinase (AMPK) leading to the reduction in acetyl-CoA carboxylase activity. In brown adipocytes 1,1-Dimethylbiguanide, Hydrochloride has been observed to inhibit leptin secretion via a mitogen-activated protein kinase signalling pathway.
Technical Information
Appearance:Crystalline
Physical State:Solid
Solubility:Soluble in water (50 mg/ml), ethanol, and DMSO (50 mM).
Storage:Store at 4° C
Melting Point:223-226 °C (lit.)
Boiling Point:224.1 °C at 760 mmHg
IC50:Streptococcus sp. 'group A': EC5050 = 4.08 µM; Streptokinase A: EC5050 = 5.65 µM (Streptococcus pyogenes serotype M1)
pK Values:pKb: 12.25 (Predicted)
Safety and Reference Information
WGK Germany:3
RTECS:DU1800000
PubChem CID:14219
Merck Index:14: 5938
MDL Number:MFCD00012582
EC Number:214-230-6
SMILES:CN(C)C(=N)N=C(N)N.Cl
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
References
1. Vague, P.,et al. 1987. Thromb. Haemost. 57: 326-328. PMID: 3310318
2. Rossetti, L., et al. 1990. Metab. Clin. Exp. 39: 425-435. PMID: 2157941
3. Stith, B.J., et al. 1996. Endocrinology. 137: 2990-2999. PMID: 8770923
4. Lin, H.Z., et al. 2000. Nat. Med. 6: 998-1003. PMID: 10973319
5. Zhou, G., et al. 2001. J. Clin. Invest. 108: 1167-1174. PMID: 11602624
6. Cleasby, M.E., et al. 2004. Diabetes. 53: 3258-3266. PMID: 15561958
7. Klein, J., et al. 2004. J. Endocrinol. 183: 299-307. PMID: 15531718
8. Mohiuddin, M., et al. 2009. Pak. J. Biol. Sci. 12: 734-737. PMID: 19634481
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