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  • 1115-70-4 Structure
  • Basic information

    1. Product Name: 1,1-Dimethylbiguanide hydrochloride
    2. Synonyms: gliformin;haurymellin;meguan;n,n-dimethylbiguanidehydrochloride;n,n-dimethyl-imidodicarbonimidicdiamidmonohydrochloride;1,1-DIMETHYLBIGUANIDE HYDROCHLORIDE;METFORMIN HCL;METFORMIN HYDROCHLORIDE
    3. CAS NO:1115-70-4
    4. Molecular Formula: C4H11N5*ClH
    5. Molecular Weight: 165.62
    6. EINECS: 214-230-6
    7. Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;API's;Miscellaneous Compounds;Aerobic Glycolysis (the Warburg Effect);Cancer Metabolism;Inhibitors and Activators of the AMPK pathway;Inhibitors of Aerobic Glycolysis (the Warburg Effect);Building Blocks;Cancer Research;Chemical Synthesis;Guanidines;Nitrogen Compounds;Organic Building Blocks;API;FORTAMET;Diabetes Research;Inhibitors
    8. Mol File: 1115-70-4.mol
    9. Article Data: 14
  • Chemical Properties

    1. Melting Point: 223-226 °C(lit.)
    2. Boiling Point: 224.1 °C at 760 mmHg
    3. Flash Point: 9℃
    4. Appearance: White/Powder
    5. Density: 1.36[at 20℃]
    6. Vapor Pressure: 0.0929mmHg at 25°C
    7. Refractive Index: N/A
    8. Storage Temp.: Store at RT
    9. Solubility: Freely soluble in water, slightly soluble in alcohol, practically insoluble in acetone and in methylene chloride
    10. PKA: 12.4[at 20 ℃]
    11. Water Solubility: Soluble in water (50 mg/ml), ethanol, and DMSO (50 mM).
    12. Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 2 months.
    13. Merck: 14,5938
    14. CAS DataBase Reference: 1,1-Dimethylbiguanide hydrochloride(CAS DataBase Reference)
    15. NIST Chemistry Reference: 1,1-Dimethylbiguanide hydrochloride(1115-70-4)
    16. EPA Substance Registry System: 1,1-Dimethylbiguanide hydrochloride(1115-70-4)
  • Safety Data

    1. Hazard Codes: Xn,T,F
    2. Statements: 22-36/38-39/23/24/25-23/24/25-11
    3. Safety Statements: 26-36-45-36/37-16-7
    4. RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
    5. WGK Germany: 3
    6. RTECS: DU1800000
    7. HazardClass: N/A
    8. PackingGroup: N/A
    9. Hazardous Substances Data: 1115-70-4(Hazardous Substances Data)

1115-70-4 Usage

Description

1,1-Dimethylbiguanide hydrochloride, also known as Metformin, is a versatile biguanide with a wide range of biological activities. It is a strong base that forms well-defined salts and exhibits excellent coordination capacity with transition metals, resulting in highly colored bidentate chelate complexes. Metformin exists in various forms, including diprotonated (H2MET)2+ in strong acidic solution, monoprotonated (HMET)+ in weak acid, MET in neutral, and deprotonated (MET)in strong alkali solution. It is a widely used oral antidiabetic drug, known for its ability to increase plasma active glucagon-like peptide-1 (GLP-1) levels in humans.

Uses

1. Used in Pharmaceutical Industry:
1,1-Dimethylbiguanide hydrochloride is used as a pharmaceutical primary standard for the determination of the analyte in pharmaceutical formulations and human plasma samples by analytical techniques.
2. Used in Anti-diabetic Applications:
1,1-Dimethylbiguanide hydrochloride is used as an antidiabetic agent for treating polycystic ovary syndrome, non-alcoholic fatty liver disease, and diabetes mellitus type 2. It enhances insulin sensitivity and reduces blood glucose levels by inhibiting hepatic gluconeogenesis and increasing glucose utilization in peripheral tissues.
3. Used in Anti-cancer Applications:
1,1-Dimethylbiguanide hydrochloride exhibits anti-diabetic and anti-cancer activity, reducing tumor growth in certain cancer models and potentially enhancing the efficacy of conventional chemotherapeutic drugs.
4. Used in Hypoglycemic Agents:
1,1-Dimethylbiguanide hydrochloride is used in hypoglycemic agents, particularly for non-insulin-dependent diabetes. It increases the sensitivity of peripheral tissues to insulin, enhances insulin-mediated glucose utilization, and inhibits hepatic glucose output.
5. Used in Drug Delivery Systems:
Metformin hydrochloride may be used in novel drug delivery systems to overcome limitations and enhance its applications and efficacy against cancer cells, employing various organic and metallic nanoparticles as carriers for improved delivery, bioavailability, and therapeutic outcomes.
Chemical Properties:
1,1-Dimethylbiguanide hydrochloride is a white crystal or crystalline powder with a melting point of 232℃ (218-220℃). It is soluble in water and methanol, slightly soluble in ethanol, and insoluble in ether and chloroform. The compound has an odorless, bitter taste.
Brand Names:
Some of the brand names for 1,1-Dimethylbiguanide hydrochloride include Fortamet (Andrx), Glucophage (Bristol-Myers Squibb), Glumetza (Depomed), and Riomet (Ranbaxy).

Oral hypoglycemic agents

Metformin hydrochloride is a biguanide oral hypoglycemic agent , also known as? Glucophage,? its hypoglycemic effect is weaker than phenformin, the main role is to reduce the glucagon secretion of A cells ,and to promote the conversion of glucose to glycogen, its characteristic effect including that it does not? stimulate pancreatic β-cells to secrete insulin . The follows are hypoglycemic mechanisms: 1. Increasing the sensitivity of peripheral tissues to insulin, increase insulin-mediated glucose utilization. 2. Increasing glucose utilization of non-insulin-dependent tissues, such as brain, blood cells, kidney medulla, intestine, skin and so on. 3. Inhibiting hepatic gluconeogenesis effect , reducing hepatic glucose output. 4. Inhibiting glucose uptake by intestinal cells. 5. Inhibiting the biosynthesis and storage of cholesterol , lowering blood triglycerides and total cholesterol levels. Metformin hydrochloride is clinically used for the treatment of type Ⅱ diabetes patients who are not satisfied with simple diet control, especially patients with obesity and hyperinsulinemia, usage of this drug not only displays no hypoglycemic effect, but also there may be weight loss and hyperinsulinemia effect. For some patients with poor efficacy of sulfonylurea ,it may be effective, if it is used with hypoglycemic drugs including sulfonylurea, intestinal glucosidase inhibitors or thiazolidinediones, the results are better than used alone. It can also be used in patients with insulin therapy to reduce the amount of insulin. At present, domestic manufacturer mainly include the American Shanghai Squibb Pharmaceutical Co., Ltd .

Adverse effects and precautions

Biguanide oral hypoglycemic agents can increase glucose utilization of surrounding tissues and inhibit the intestinal absorption of glucose, and inhibit glycogen gluconeogenesis and hepatic glucose output,it is mainly applied to obesity, dyslipidemia, type II diabetes patients. It almost has no hypoglycemic effect for normal persons ,? 2 to 3 hours after taking for diabetes patients ,glucose decreases significantly. Commonly used oral hypoglycemic agents include phenformin and metformin hydrochloride. The incidence of adverse effects of metformin hydrochloride is higher than tolbutamide , common gastrointestinal reactions are anorexia, nausea, vomiting, abdominal pain, diarrhea, occasional metallic taste in the mouth, bad breath, nausea, loss of appetite and diarrhea and other gastrointestinal reactions, sometimes? hypoglycemia? is visible? . Since the biguanide drugs enhance sugar anaerobic glycolysis, and inhibit? glycogen generation, small number of patients may suffer with ketosis or lactic acidosis, which should be particularly vigilant, but metformin effect is weak? , adverse reactions are only? 1/50 of other biguanides, and it has rapid clearance, there are no accumulation in the liver, it rarely induces lactic acidosis, sometimes there is mild increase in blood lactate. patients with heart, liver, kidney diseases are prone to these adverse reactions, diabetes patients with these types of complications are hanged. It can reduce the absorption of vitamin B12, but it seldom causes anemia. The following cases are contraindications: 1. Pregnant and lactating women, children under 10 years of age, 80 years of age or older. 2. Diabetic ketoacidosis, diabetic hyperglycemic hyperosmolar syndrome, diabetes lactic acidosis. 3. Severe liver and kidney dysfunction, blood urea nitrogen and creatinine higher than normal, hypovolemic shock, heart failure, AMI, in vivo hypoxic condition such as heart failure, pulmonary insufficiency, or any systemic hypoxia circumstances and other serious heart and lung diseases. 4. Severe infection or trauma, major surgery, clinical hypotension , hypoxia and so on. 5. Complications with severe diabetic nephropathy and retinopathy. When there are symptoms,the drug? should be immediately discontinued; cimetidine can reduce the renal excretion of metformin hydrochloride, agar types can reduce the absorption of metformin, patients must check liver and kidney function and cardiac ketones regularly. 6. Alcoholics, vitamin B12 and folate deficiency which are not corrected.

Production method

After the salifying of dimethylamine and the reaction with dicyandiamide , the product is derived.

Originator

Diabetex ,Germania

Manufacturing Process

The boiling mixture of 1,000 L xylene, 450 kg dimethylamine and 840 kg dicyanamide was added 365 kg hydrogene chloride. Yield of biguanide, 1,1- dimethyl-, hydrochloride 1,588 kg (96%). Biguanide, 1,1-dimethyl-, hydrochloride may be recrystallysed from methanol.

Therapeutic Function

Oral hypoglycemic

Flammability and Explosibility

Nonflammable

Biological Activity

Antidiabetic agent; lowers plasma glucose levels and improves insulin sensitivity. Inhibits hepatic gluconeogenesis via activation of the LKB1/AMPK pathway. Displays antiproliferative effects in cancer cell lines.

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.

Clinical Use

Non-insulin dependent diabetes mellitus Polycystic ovary syndrome

Veterinary Drugs and Treatments

Metformin may be useful in the adjunctive treatment of non-insulin dependent diabetes mellitus in cats. Only limited trials of the drug have been performed in cats, with only very limited success when the drug is used alone. Studies comparing its safety and efficacy with other oral antihyperglycemics (e.g., glipizide or insulin) were not located.

Drug interactions

Potentially hazardous interactions with other drugs Alcohol: increased risk of lactic acidosis. Cimetidine: inhibits renal excretion of metformin

Metabolism

Metformin is not metabolised to any great extent, and is entirely excreted unchanged in the urine.

References

1) Zhou et al. (2001), Role of AMP-activated protein kinase in mechanism of metformin action; J. Clin. Invest., 108 1167 2) Shaw et al. (2005), The kinase LKB1 mediates glucose homeostasis in liver and therapeutic effects of metformin; Science, 310 1642 3) Shi et al. (2012), Therapeutic metformin/AMPK activation blocked lymphoma cell growth via inhibition of mTOR pathway and induction of autophagy; Cell Death Dis., 3 e275 4) Rego et al. (2017) Anti-tumor effects of metformin on head and neck carcinoma cell lines: A systemic review; Oncol. Lett., 13 554 5) Lee et al. (2017) PGC1α Activators Mitigate Diabetic Tubulopathy by Improving Mitochondrial Dynamics and Quality Control; J. Diabetes Res., 2017 6483572 6) Zheng et al. (2012) Sirtuin 1-mediated cellular metabolic memory of high glucose via the LKB1/AMPK/ROS pathway and therapeutic effects of metformin; Diabetes, 61 217 7) Katila et al. (2017) Metformin lowers α-synuclein phosphorylation and upregulates neurotrophic factor in the MPTP mouse model of Parkinson’s disease; Neuropharmacology, 125 396 8) Coll et al. (2020), GDF15 mediates the effects of metformin on body weight and energy balance; Nature, 578 444

Check Digit Verification of cas no

The CAS Registry Mumber 1115-70-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 1,1,1 and 5 respectively; the second part has 2 digits, 7 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 1115-70:
(6*1)+(5*1)+(4*1)+(3*5)+(2*7)+(1*0)=44
44 % 10 = 4
So 1115-70-4 is a valid CAS Registry Number.
InChI:InChI=1/C4H11N5.ClH/c1-9(2)4(7)8-3(5)6;/h1-2H3,(H5,5,6,7,8);1H

1115-70-4 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • TCI America

  • (M2009)  Metformin Hydrochloride  >98.0%(HPLC)(T)

  • 1115-70-4

  • 25g

  • 880.00CNY

  • Detail
  • TCI America

  • (M2009)  Metformin Hydrochloride  >98.0%(HPLC)(T)

  • 1115-70-4

  • 100g

  • 2,620.00CNY

  • Detail
  • Sigma-Aldrich

  • (M0605000)  Metforminhydrochloride  European Pharmacopoeia (EP) Reference Standard

  • 1115-70-4

  • M0605000

  • 1,880.19CNY

  • Detail
  • USP

  • (1396309)  Metforminhydrochloride  United States Pharmacopeia (USP) Reference Standard

  • 1115-70-4

  • 1396309-200MG

  • 5,477.94CNY

  • Detail
  • Cerilliant

  • (M-072)  Metforminhydrochloridesolution  1.0 mg/mL in methanol (as free base), ampule of 1 mL, certified reference material

  • 1115-70-4

  • M-072-1ML

  • 1,302.21CNY

  • Detail
  • Aldrich

  • (D150959)  1,1-Dimethylbiguanidehydrochloride  97%

  • 1115-70-4

  • D150959-5G

  • 964.08CNY

  • Detail

1115-70-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name Metformin Hydrochloride

1.2 Other means of identification

Product number -
Other names N1,N1-Dimethylbiguanide hydrochloride

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:1115-70-4 SDS

1115-70-4Relevant articles and documents

Synthetic method of metformin hydrochloride and application thereof

-

Paragraph 0029-0047, (2021/08/14)

The invention belongs to the field of medicine synthesis, and discloses a synthesis method of metformin hydrochloride and an application thereof, the synthetic method comprises the following steps: dissolving dicyandiamide and dimethylamine in lower alcohol, adding sodium alkoxide, uniformly mixing, gradually raising the temperature for condensation reaction, and after the reaction is finished, adding hydrochloric acid to adjust the pH value to be acidic to obtain the metformin hydrochloride. According to the synthetic method of metformin hydrochloride, energy consumption in the reaction process is reduced, the production cost is reduced, and the purification difficulty of the product is reduced. The method is suitable for synthesizing the metformin hydrochloride, and the synthesized metformin hydrochloride is used for preparing the metformin hydrochloride sustained release tablets.

SOLVENT FREE CONTINUOUS PROCESS FOR THE SYNTHESIS OF METFORMIN HYROCHLORIDE

-

Paragraph 0052; 0056, (2021/03/13)

The present invention provides a continuous solvent free and additive free process for the synthesis of Metformin Hydrochloride in a screw reactor. >90% conversion of the solid substrates without solvent is obtained in a screw reactor to produce Metformin Hydrochloride with at least 90% selectivity.

Preparation method of metformin hydrochloride

-

Paragraph 0012-0013; 0014-0015; 0016-0017; 0018-0019, (2018/03/24)

The invention relates to a preparation method of metformin hydrochloride. The preparation method comprises the following steps: utilizing diphenyl ether or HMPT as a solvent to perform the reaction, refluxing when the reaction temperature is 200 DEG C, after the reaction is ended, cleaning a product with isoamyl alcohol at 100 DEG C, re-crystallizing and refining by using ethanol, so that not onlyis the reaction time shortened, but also the satisfactory yield can be realized; and in addition, a boiling point of the used solvent is far higher than the reaction temperature, so that the over-boiling phenomenon is maximally avoided.

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