D150959

1,1-Dimethylbiguanide hydrochloride

97%

• Synonym(s): Metformin
• Linear Formula: NH₂C(=NH)NHC(=NH)N(CH₃)₂ · HCl
• CAS Number: 1115-70-4
• Molecular Weight: 165.62
• EC Number: 214-230-6
• MDL number: MFCD00012582
• UNSPSC Code: 12352100
• PubChem Substance ID: 24893460
• NACRES: NA.22

Properties

• Assay: 97%
• form: crystals
• mp: 223-226 °C (lit.)
• SMILES string: Cl[H].CN(C)C(=N)NC(N)=N
• InChI: 1S/C4H11N5.ClH/c1-9(2)4(7)8-3(5)6;/h1-2H3,(H5,5,6,7,8);1H
• InChI key: OETHQSJEHLVLGH-UHFFFAOYSA-N

Description

General description

1,1-Dimethylbiguanide hydrochloride (metformin) is a strong base. It forms well defined salts and possessing excellent coordination capacity with transition metals, forming highly colored bidentate chelate complexes. Metformin (MET) exists in various forms: diprotonated (H₂MET)²⁺ in strong acidic solution, monoprotonated (HMET)⁺ in weak acid, MET in neutral and deprotonated (MET)^- in strong alkali solution. It is an oral antidiabetic drug. Pharmacokinetics of metformin has been studied. Determination of metformin in human plasma has been described by simple HPLC-UV method. Metformin is reported to increase plasma active glucagon-like peptide-1 (GLP-1) in humans.

Metformin is used as an organic base catalyst for the transesterification of coconut oil with methanol.

Application

1,1-Dimethylbiguanide hydrochloride is suitable biguanide agent used in a study to investigate its role in enhancing the secretions of plasma active glucagon-like peptide-1 (GLP-1) levels. It may be used in the synthesis of the following:

• bis(1,1-dimethylbiguanido)copper(II) octahydrate
• bis(1,1-dimethylbiguanido)nickel(II)
• 1,1-dimethylbiguanidium tetrabromothallate(III)

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.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302,H319
• Precautionary Statements: P264 - P280 - P301 + P312 - P305 + P351 + P338 - P337 + P313 - P501
• Hazard Classifications: Acute Tox. 4 Oral - Eye Irrit. 2
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 1
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves