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D150959

Sigma-Aldrich

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:
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

Quality Level

200

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.

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.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302,H319

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Metformin impurity A European Pharmacopoeia (EP) Reference Standard

Y0001590

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USP

USP

1396331

Metformin Related Compound B

AMPK Inhibitor, Compound C AMPK Inhibitor, Compound C, CAS 866405-64-3, is a cell-permeable compound that inhibits KDR/VEGFR2, ALK2/BMPR-I, and AMPK kinase activities (IC₅₀ = 25.1, 148, and 234.6 nM, respectively).

Sigma-Aldrich

171260

AMPK Inhibitor, Compound C

Dorsomorphin ≥98% (HPLC)

Sigma-Aldrich

P5499

Dorsomorphin

AICAR ≥98% (HPLC), powder

Sigma-Aldrich

A9978

AICAR

Bis (1,1-dimethylbiguanido) copper (II) octahydrate.
Zhu M, et al.
Acta Crystallographica Section E, Structure Reports Online, 58(5), 217-219 (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) nickel (II).
Zhu M, et al.
Acta Crystallographica Section E, Structure Reports Online, 58(6), 272-274 (2002)
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
Eric P Kusnadi et al.
The EMBO journal, 39(21), e105111-e105111 (2020-09-19)
Elevated ribosome biogenesis in oncogene-driven cancers is commonly targeted by DNA-damaging cytotoxic drugs. Our previous first-in-human trial of CX-5461, a novel, less genotoxic agent that specifically inhibits ribosome biogenesis via suppression of RNA polymerase I (Pol I) transcription, revealed single-agent
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