1-carbamimidamido-N,N-dimethylmethanimidamide hydrochloride

• ChemBase ID: 72826
• Molecular Formular: C4H12ClN5
• Molecular Mass: 165.62458
• Monoisotopic Mass: 165.07812309
• SMILES: NC(=N)NC(=N)N(C)C.Cl
• Canonical SMILES: CN(C(=N)NC(=N)N)C.Cl
• InChI: InChI=1S/C4H11N5.ClH/c1-9(2)4(7)8-3(5)6;/h1-2H3,(H5,5,6,7,8);1H
• InChIKey: OETHQSJEHLVLGH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-carbamimidamido-N,N-dimethylmethanimidamide hydrochloride
• IUPAC Traditional name: metformin hydrochloride; 1-carbamimidamido-N,N-dimethylmethanimidamide hydrochloride
• Synonyms: Glucophage; Riomet; Diabex; Metformin hydrochloride; Metformin hydrochloride; 1,1-Dimethylbiguanide hydrochloride; N,N-Dimethylimidodicarbonimidic Diamide Hydrochloride; Diabetosan; Metiguanide; Glucoform; Glucomet; Glucomin; Glucomine; Orabet; Siamformet; Walaphage; Diabetase; Fluamine; Gliguamid; Glucamet; Glucinan; Glucophege; Stagid; 1-carbamimidamido-N,N-dimethylmethanimidamide hydrochloride; Metformin; 1,1-DIMETHYLBIGUANIDE HYDROCHLORIDE; N,N-Dimethylimidodicarbonimidic diamine; 1,1-Dimethylbiguanide hydrochloride; METFORMIN; 甲福明 盐酸盐; 二甲双胍 盐酸盐; 二甲双胍; 甲福明 盐酸盐

Database IDs

• CAS Number: 1115-70-4
• EC Number: 214-230-6
• MDL Number: MFCD00012582
• PubChem SID: 24893460; 162037747; 24893918
• PubChem CID: 14219

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -5.7474184
• LogD (pH = 7.4): -5.6176996
• Log P: -0.91842926
• Molar Refractivity: 56.6427 cm^3
• Polarizability: 12.998098 Å^3
• Polar Surface Area: 88.99 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: White Solid
• Melting Point: 218-220°C; 220-226°C; 223-226 °C(lit.); 223-226°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer; Room Temperature (15-30°C); Room Temperature (15-30°C), Desiccate
• RTECS: DU1800000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/38; R:22
• Safety Statements: 26-36; S:36/37/39
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319
• GHS Precautionary statements: P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Mechanism of Action: Stimulator of hepatic enzyme AMP-activated protein kinase (AMPK)

Product Information

• Purity: ≥97%; 97%; 98%
• Salt Data: HCL; HCl
• Application(s): Oral hypoglycaemic agent; Used for treatment of type 2 diabetes
• Pharmacopeia Traceability: traceable to PhEur M0605000; traceable to USP 1396309
• Linear Formula: NH2C(=NH)NHC(=NH)N(CH3)2 · HCl

DETAILS

MP Biomedicals - 02151691

Hydrochloride
Purity: 98%
White crystalline powder.

MP Biomedicals - 02157805

Hydrochloride

Selleck Chemicals - S1950

Research Area: Endocrinology
Biological Activity:
Metformin hydrochloride(Glucophage) is a biguanide hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. Metformin improves glycemic control by improving insulin sensitivity and decreasing intestinal absorption of glucose. Metformin’s pharmacologic mechanisms of action are different from other classes of oral antihyperglycemic agents. Metformin decreases hepatic glucose production, decreases intestinal absorption of glucose, and improves insulin sensitivity by increasing peripheral glucose uptake and utilization. [1]

Sigma Aldrich - D5035

Biochem/physiol Actions
甲福明是一种抗糖尿病药，可降低血糖水平，提高胰岛素灵敏度。其代谢作用（包括抑制肝脏糖异生作用）至少部分是通过激活 LKB1-AMPK（AMP-活化蛋白激酶）通路进行介导。该通路的激活也涉及到癌细胞系中甲福明的抗增殖和促凋亡作用。

Sigma Aldrich - D150959

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Biochem/physiol Actions
Metformin is an antidiabetic agent that reduces blood glucose levels and improves insulin sensitivity. Its metabolic effects, including the inhibition of hepatic gluconeogenesis, are mediated at least in part by activation of the LKB1-AMPK (AMP-activated protein kinase) pathway. Activation of this pathway also appears to be involved in the antiproliferative and proapoptotic actions of metformin in cancer cell lines.
Packaging
5 g in glass bottle

Sigma Aldrich - 04635

Biochem/physiol Actions
Metformin is an antidiabetic agent that reduces blood glucose levels and improves insulin sensitivity. Its metabolic effects, including the inhibition of hepatic gluconeogenesis, are mediated at least in part by activation of the LKB1-AMPK (AMP-activated protein kinase) pathway. Activation of this pathway also appears to be involved in the antiproliferative and proapoptotic actions of metformin in cancer cell lines.

Toronto Research Chemicals - M258815

An oral hypoglycemic agent.

REFERENCES

• http://www.drugbank.ca/drugs/DB00331
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• Werner, E.A. et al., J.C.S., 1922, 1790, (synth)
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• Beckmann, R. et al., CA, 1970, 72, 30102p, (metab)
• Nandi, S.D., Tetrahedron, 1972, 28, 845, (uv, deriv)
• Hermann, L.S., Diabetes/Metab. Rev., 1979, 5, 233, (rev)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 247, (synonyms)
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• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, DQR600; DQR800