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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
Pricing and availability is not currently available.

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.[1] 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.[2] It is an oral antidiabetic drug. Pharmacokinetics of metformin has been studied.[3] Determination of metformin in human plasma has been described by simple HPLC-UV method.[4] Metformin is reported to increase plasma active glucagon-like peptide-1 (GLP-1) in humans.[5]

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.[5] It may be used in the synthesis of the following:
  • bis(1,1-dimethylbiguanido)copper(II) octahydrate[1]
  • bis(1,1-dimethylbiguanido)nickel(II)[2]
  • 1,1-dimethylbiguanidium tetrabromothallate(III)[6]

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

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

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF1779V
BCCJ4785
WXBD2659V
BCCC7544
BCCB9983

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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
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)
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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Questions

1–7 of 7 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  3. Is this product (D150959) cell culture grade and how is it solved?

    1 answer

    1. This material is soluble at 8 mg/mL in DMSO and 16 mg/mL in water. The product has not been tested for use in cell culture applications but has been used successfully by other researchers. Please see the link below to review the available publications:
      https://www.sigmaaldrich.com/search/d150959?focus=papers&page=1&perpage=30&sort=relevance&term=D150959&type=citation_search

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  4. What are the recommended storage conditions for metformin crystals? What are the storage conditions and stability duration of metformin once it is dissolved in water?

    1 answer

    1. This product may be stored at room temperature. Stock solutions prepared in distilled water may be stored in aliquots at -20° for up to 2 months.

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  5. What is the recommended method for reconstituting item D150959, 1,1-Dimethylbiguanide hydrochloride?

    1 answer

    1. This item is soluble in DMSO (up to 8 mg/ml) or in water (up to 16 mg/ml).

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  6. What is the Department of Transportation shipping information for this product?

    1 answer

    1. Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product.

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  7. What solvents can be used to dissolve Product D150959, 1,1-Dimethylbiguanide hydrochloride?

    1 answer

    1. According to the chemicals encyclopedia published by the Royal Society of Chemistry, 1,1-dimethylbiguanide hydrochloride is expected to be soluble in water, or in 95% alcohol.

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