D150959
1,1-Dimethylbiguanide hydrochloride
97%
Synonym(s):
Metformin
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About This Item
Linear Formula:
NH2C(=NH)NHC(=NH)N(CH3)2 · HCl
CAS Number:
Molecular Weight:
165.62
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
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
Gene Information
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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.
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.
signalword
Warning
hcodes
Hazard Classifications
Acute Tox. 4 Oral - Eye Irrit. 2
Storage Class
11 - Combustible Solids
wgk_germany
WGK 1
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
dust mask type N95 (US), Eyeshields, Gloves
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Nobuyuki Yasuda et al.
Biochemical and biophysical research communications, 298(5), 779-784 (2002-11-07)
Metformin was reported to increase plasma active glucagon-like peptide-1 (GLP-1) in humans. There are two possible mechanisms for this effect: (1) metformin inhibits dipeptidyl peptidase IV (DPPIV), an enzyme degrading GLP-1, and (2) metformin enhances GLP-1 secretion. To elucidate the
Bis (1, 1-dimethylbiguanido) nickel (II).
Zhu M, et al.
Acta Crystallographica Section E, Structure Reports Online, 58(6), 272-274 (2002)
1,1-Dimethylbiguanidium tetrabromothallate (III).
He Z, et al.
Acta Crystallographica Section E, Structure Reports Online, 58(11), m647-m649 (2002)
Bis (1,1-dimethylbiguanido) copper (II) octahydrate.
Zhu M, et al.
Acta Crystallographica Section E, Structure Reports Online, 58(5), 217-219 (2002)
Eric P Kusnadi et al.
The EMBO journal, 39(21), e105111-e105111 (2020-09-19)
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