Product Name

  • Name

    Metformin

  • EINECS 211-517-8
  • CAS No. 657-24-9
  • Article Data49
  • CAS DataBase
  • Density 1.28 g/cm3
  • Solubility
  • Melting Point 199-200 °C
  • Formula C4H11N5
  • Boiling Point 224.1 °C at 760 mmHg
  • Molecular Weight 129.165
  • Flash Point 89.3 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 657-24-9 (Metformin)
  • Hazard Symbols
  • Synonyms Biguanide,1,1-dimethyl- (6CI,8CI);1,1-Dimethylbiguanide;Cidophage;DMGG;Dimethylbiguanide;Emiphage;Ficonax;Fluamine;Flumamine;Gliguanid;Glucofine;Haurymelin;Metiguanide;Metphage;N,N-Dimethyl-imidodicarbonimidic diamide;N,N-Dimethylbiguanide;N,N-Dimethyldiguanide;N1,N1-Dimethylbiguanide;NNDG;N'-Dimethylguanylguanidine;Siofor;Imidodicarbonimidicdiamide, N,N-dimethyl-;
  • PSA 88.99000
  • LogP 0.25650

Synthetic route

metformin hydrochloride
1115-70-4

metformin hydrochloride

dimethylbiguanide
657-24-9

dimethylbiguanide

Conditions
ConditionsYield
With sodium hydroxide In water at 20℃; for 0.5h;100%
With sodium hydroxide In water at 20℃; for 0.5h;99%
With sodium hydroxide In ethanol for 5h;99%
N,N-dimethylimidodicarbonimidic diamide hydrochloride

N,N-dimethylimidodicarbonimidic diamide hydrochloride

dimethylbiguanide
657-24-9

dimethylbiguanide

Conditions
ConditionsYield
With sodium hydroxide In isopropyl alcohol at 0 - 40℃; for 18.2h; Temperature; Solvent;93%
With sodium hydroxide In isopropyl alcohol at 39.84℃; for 3h;
With sodium In ethanol at 60℃; for 1h; Reagent/catalyst; Solvent; Temperature;
N,N-dimethylammonium chloride
506-59-2

N,N-dimethylammonium chloride

N-Cyanoguanidine
127099-85-8, 780722-26-1

N-Cyanoguanidine

dimethylbiguanide
657-24-9

dimethylbiguanide

Conditions
ConditionsYield
at 130 - 140℃;
In butan-1-ol for 6h; Reflux;
N-Cyanoguanidine
127099-85-8, 780722-26-1

N-Cyanoguanidine

dimethylamine-

dimethylamine-

dimethylbiguanide
657-24-9

dimethylbiguanide

Conditions
ConditionsYield
at 160℃;
dimethyl amine
124-40-3

dimethyl amine

N-Cyanoguanidine
127099-85-8, 780722-26-1

N-Cyanoguanidine

A

dimethylbiguanide
657-24-9

dimethylbiguanide

B

N,N-dimethyl-guanidine

N,N-dimethyl-guanidine

Conditions
ConditionsYield
at 180℃; beim Erhitzen des Hydrochlorids;
...Expand
N1,N1-dimethyl-S-cyclohexyl-N4-thiohydroxybiguanidine
1170667-82-9

N1,N1-dimethyl-S-cyclohexyl-N4-thiohydroxybiguanidine

dimethylbiguanide
657-24-9

dimethylbiguanide

Conditions
ConditionsYield
With hydrogenchloride In water at 37℃; pH=1.0; Reactivity;
N1,N1-dimethyl-S-phenyl-N4-thiohydroxybiguanidine
1170667-83-0

N1,N1-dimethyl-S-phenyl-N4-thiohydroxybiguanidine

dimethylbiguanide
657-24-9

dimethylbiguanide

Conditions
ConditionsYield
With human serum at 37℃; pH=7.4; Reactivity; Enzymatic reaction; Aqueous phosphate buffer;
N,N-dimethylebiguanidinium chloride
1378856-94-0

N,N-dimethylebiguanidinium chloride

dimethylbiguanide
657-24-9

dimethylbiguanide

Conditions
ConditionsYield
With sodium hydroxide In ethanol for 2h;
dimethylbiguanide
657-24-9

dimethylbiguanide

(R)-1,2-dithiolane-3-pentanoic acid
1200-22-2

(R)-1,2-dithiolane-3-pentanoic acid

N,N-dimethylimidodicarbonimidic diamide R-(+)-lipoate
959986-37-9

N,N-dimethylimidodicarbonimidic diamide R-(+)-lipoate

Conditions
ConditionsYield
In methanol for 2h; Product distribution / selectivity;100%
In acetonitrile for 0.166667h; Product distribution / selectivity;95%
In acetone for 0.166667 - 0.5h; Product distribution / selectivity;95%
In methanol; acetone for 0.333333h; Product distribution / selectivity;
((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyl)-L-leucyl-L-leucinate

((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyl)-L-leucyl-L-leucinate

dimethylbiguanide
657-24-9

dimethylbiguanide

amino(3,3-dimethylguanidino)methaniminium (S)-2-((S)-2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenamido)-4-methylpentanamido)-4-methylpentanoate

amino(3,3-dimethylguanidino)methaniminium (S)-2-((S)-2-((5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenamido)-4-methylpentanamido)-4-methylpentanoate

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 1h;100%
all cis-5,8,11,14,17-eicosapentaenoic acid
10417-94-4

all cis-5,8,11,14,17-eicosapentaenoic acid

L-leucyl-L-leucine
3303-31-9

L-leucyl-L-leucine

dimethylbiguanide
657-24-9

dimethylbiguanide

C12H24N2O3*C4H11N5*C20H30O2

C12H24N2O3*C4H11N5*C20H30O2

Conditions
ConditionsYield
In methanol at 20℃; for 5h;100%
...Expand
((6Z,9Z,12Z)-octadeca-6,9,12-trienoyl)-L-isoleucyl-L-isoleucine

((6Z,9Z,12Z)-octadeca-6,9,12-trienoyl)-L-isoleucyl-L-isoleucine

dimethylbiguanide
657-24-9

dimethylbiguanide

((6Z,9Z,12Z)-octadeca-6,9,12-trienoyl)-L-isoleucyl-L-isoleucine N,N-dimethyl-imidodicarbonimidic diamide

((6Z,9Z,12Z)-octadeca-6,9,12-trienoyl)-L-isoleucyl-L-isoleucine N,N-dimethyl-imidodicarbonimidic diamide

Conditions
ConditionsYield
In water; acetone at 50℃; for 6h;99.6%
all cis-5,8,11,14,17-eicosapentaenoic acid
10417-94-4

all cis-5,8,11,14,17-eicosapentaenoic acid

L-Aspartic acid
56-84-8

L-Aspartic acid

dimethylbiguanide
657-24-9

dimethylbiguanide

bis[{[(dimethylamino)(imino)methyl]amino}(imino)methanaminium]-(5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoate-(3S)-3-ammonio-3-carboxypropanoate

bis[{[(dimethylamino)(imino)methyl]amino}(imino)methanaminium]-(5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoate-(3S)-3-ammonio-3-carboxypropanoate

Conditions
ConditionsYield
In methanol at 60℃; for 1.5h;99%
...Expand
Adipic acid
124-04-9

Adipic acid

dimethylbiguanide
657-24-9

dimethylbiguanide

metformin adipate (2:1)

metformin adipate (2:1)

Conditions
ConditionsYield
In methanol at 40℃; Product distribution / selectivity;98.9%
In methanol; ethyl acetate at 40℃; Product distribution / selectivity;98.9%
In water; acetone at 20 - 40℃; Product distribution / selectivity;93.9%
dimethylbiguanide
657-24-9

dimethylbiguanide

butyric acid
107-92-6

butyric acid

metformin butyric acid salt
1261952-47-9

metformin butyric acid salt

Conditions
ConditionsYield
In acetone at 20℃; for 2h;98%
((7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyl)-L-isoleucine

((7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyl)-L-isoleucine

dimethylbiguanide
657-24-9

dimethylbiguanide

((7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyl)-L-isoleucine N,N-dimethyl-imidodicarbonimidic diamide

((7Z,10Z,13Z,16Z,19Z)-docosa-7,10,13,16,19-pentaenoyl)-L-isoleucine N,N-dimethyl-imidodicarbonimidic diamide

Conditions
ConditionsYield
In water; acetone at 50℃; for 6h;98%
formaldehyd
50-00-0

formaldehyd

5-chloroindole 2,3-dione
17630-76-1

5-chloroindole 2,3-dione

dimethylbiguanide
657-24-9

dimethylbiguanide

2-(piperazin-1-ylmethyl)-1H-benzimidazole
59052-85-6

2-(piperazin-1-ylmethyl)-1H-benzimidazole

C25H29ClN10O

C25H29ClN10O

Conditions
ConditionsYield
With sulfonic acid immobilized on metformin-p-formylbenzoic acid-based schiff base-coated Fe3O4 nanocatalyst In ethanol for 2h; Reflux;98%
...Expand
formaldehyd
50-00-0

formaldehyd

5-methyl-indole-2,3-dione
608-05-9

5-methyl-indole-2,3-dione

dimethylbiguanide
657-24-9

dimethylbiguanide

2-(piperazin-1-ylmethyl)-1H-benzimidazole
59052-85-6

2-(piperazin-1-ylmethyl)-1H-benzimidazole

C26H32N10O

C26H32N10O

Conditions
ConditionsYield
With sulfonic acid immobilized on metformin-p-formylbenzoic acid-based schiff base-coated Fe3O4 nanocatalyst In ethanol for 2h; Reflux;98%
...Expand
2-hydroxy-benzoic acid, 2-carboxyphenyl ester
552-94-3

2-hydroxy-benzoic acid, 2-carboxyphenyl ester

dimethylbiguanide
657-24-9

dimethylbiguanide

{[amino(imino)methyl]amino}(dimethylamino)methaniminium 2-[(2-hydroxybenzoyl)oxy]benzoate
1411413-55-2

{[amino(imino)methyl]amino}(dimethylamino)methaniminium 2-[(2-hydroxybenzoyl)oxy]benzoate

Conditions
ConditionsYield
In acetonitrile at 0 - 20℃; for 2h;96%
5-chloroindole 2,3-dione
17630-76-1

5-chloroindole 2,3-dione

dimethylbiguanide
657-24-9

dimethylbiguanide

C12H13ClN6O

C12H13ClN6O

Conditions
ConditionsYield
With sulfonic acid immobilized on metformin-p-formylbenzoic acid-based schiff base-coated Fe3O4 nanocatalyst In ethanol Reflux;96%
(S)-2-ethoxy-3-(4-(2-(2-methyl-5-(4-(methylthio)phenyl)-1H-pyrrol-1-yl)ethoxy)phenyl)propanoic acid

(S)-2-ethoxy-3-(4-(2-(2-methyl-5-(4-(methylthio)phenyl)-1H-pyrrol-1-yl)ethoxy)phenyl)propanoic acid

L-glutamic acid
56-86-0

L-glutamic acid

dimethylbiguanide
657-24-9

dimethylbiguanide

metformin-L-glutamic acid-(S)-2-ethoxy-3-(4-(2-(2-methyl-5-(4-(methylthio)phenyl)-1H-pyrrol-1-yl)ethoxy)phenyl)propanoic acid salt

metformin-L-glutamic acid-(S)-2-ethoxy-3-(4-(2-(2-methyl-5-(4-(methylthio)phenyl)-1H-pyrrol-1-yl)ethoxy)phenyl)propanoic acid salt

Conditions
ConditionsYield
Stage #1: L-glutamic acid; dimethylbiguanide In methanol at 30℃; for 0.5h;
Stage #2: (S)-2-ethoxy-3-(4-(2-(2-methyl-5-(4-(methylthio)phenyl)-1H-pyrrol-1-yl)ethoxy)phenyl)propanoic acid In methanol at 30℃; for 48h;		95.4%
...Expand
1,5-pentanedioic acid
110-94-1

1,5-pentanedioic acid

dimethylbiguanide
657-24-9

dimethylbiguanide

metformin glutarate (2:1)

metformin glutarate (2:1)

Conditions
ConditionsYield
Stage #1: dimethylbiguanide In water; acetone at 40℃;
Stage #2: 1,5-pentanedioic acid In water; acetone at 10℃; Product distribution / selectivity;		95.3%
In water; acetone at 10 - 40℃; Product distribution / selectivity;95.3%
In ethanol at 10 - 20℃; Product distribution / selectivity;62.8%
With sodium hydroxide In ethanol at 70℃; Product distribution / selectivity;57.7%
In methanol at 40℃; Product distribution / selectivity;43.8%
formaldehyd
50-00-0

formaldehyd

5-Bromo-1H-indole-2,3-dione
87-48-9

5-Bromo-1H-indole-2,3-dione

dimethylbiguanide
657-24-9

dimethylbiguanide

2-(piperazin-1-ylmethyl)-1H-benzimidazole
59052-85-6

2-(piperazin-1-ylmethyl)-1H-benzimidazole

C25H27BrN10O

C25H27BrN10O

Conditions
ConditionsYield
With sulfonic acid immobilized on metformin-p-formylbenzoic acid-based schiff base-coated Fe3O4 nanocatalyst In ethanol for 2h; Reflux;95%
...Expand
formaldehyd
50-00-0

formaldehyd

5-Bromo-1H-indole-2,3-dione
87-48-9

5-Bromo-1H-indole-2,3-dione

dimethylbiguanide
657-24-9

dimethylbiguanide

2-(piperazin-1-ylmethyl)-1H-benzimidazole
59052-85-6

2-(piperazin-1-ylmethyl)-1H-benzimidazole

C25H29BrN10O

C25H29BrN10O

Conditions
ConditionsYield
With sulfonic acid immobilized on metformin-p-formylbenzoic acid-based schiff base-coated Fe3O4 nanocatalyst In ethanol for 2h; Reflux;95%
...Expand
formaldehyd
50-00-0

formaldehyd

5-chloroindole 2,3-dione
17630-76-1

5-chloroindole 2,3-dione

dimethylbiguanide
657-24-9

dimethylbiguanide

2-(piperazin-1-ylmethyl)-1H-benzimidazole
59052-85-6

2-(piperazin-1-ylmethyl)-1H-benzimidazole

C25H27ClN10O

C25H27ClN10O

Conditions
ConditionsYield
With sulfonic acid immobilized on metformin-p-formylbenzoic acid-based schiff base-coated Fe3O4 nanocatalyst In ethanol for 2h; Reflux;95%
...Expand
ursolic acid
77-52-1

ursolic acid

dimethylbiguanide
657-24-9

dimethylbiguanide

ursolic acid metformin salt
1541169-42-9

ursolic acid metformin salt

Conditions
ConditionsYield
In acetonitrile for 16h;94%
cis-dichlorobis(dimethylsulfoxide)platinum(II)
75992-73-3, 25794-47-2, 30729-25-0, 15274-33-6, 22840-91-1, 14568-13-9

cis-dichlorobis(dimethylsulfoxide)platinum(II)

dimethylbiguanide
657-24-9

dimethylbiguanide

[Pt(metformin)(dimethylsulfoxide)Cl]Cl
164177-46-2

[Pt(metformin)(dimethylsulfoxide)Cl]Cl

Conditions
ConditionsYield
In methanol; water at 20℃; for 24h;93.6%
5-Bromo-1H-indole-2,3-dione
87-48-9

5-Bromo-1H-indole-2,3-dione

dimethylbiguanide
657-24-9

dimethylbiguanide

C12H13BrN6O

C12H13BrN6O

Conditions
ConditionsYield
With sulfonic acid immobilized on metformin-p-formylbenzoic acid-based schiff base-coated Fe3O4 nanocatalyst In ethanol Reflux;93%
trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

dimethylbiguanide
657-24-9

dimethylbiguanide

N-(trifluoromethanesulfonyl)metformin

N-(trifluoromethanesulfonyl)metformin

Conditions
ConditionsYield
With potassium hydroxide In acetone at 20℃;92%
dimethylbiguanide
657-24-9

dimethylbiguanide

4-Methoxybenzyl alcohol
105-13-5

4-Methoxybenzyl alcohol

6-(4-methoxyphenyl)-N2,N2-dimethyl-1,3,5-triazine-2,4-diamine
43153-42-0

6-(4-methoxyphenyl)-N2,N2-dimethyl-1,3,5-triazine-2,4-diamine

Conditions
ConditionsYield
With potassium tert-butylate In 1,4-dioxane at 100℃; for 10h;92%
pseudothiohydantoin
556-90-1

pseudothiohydantoin

dimethylbiguanide
657-24-9

dimethylbiguanide

C4H11N5*C3H4N2OS

C4H11N5*C3H4N2OS

Conditions
ConditionsYield
In ethanol at -10 - 80℃; Inert atmosphere;92%
docosahexaenoic acid
6217-54-5

docosahexaenoic acid

dimethylbiguanide
657-24-9

dimethylbiguanide

metformin DHA salt
1384513-23-8

metformin DHA salt

Conditions
ConditionsYield
In acetonitrile at 20℃; for 1.08333h; Darkness;91%
With Tocopherol In methanol; ethyl acetate at 55℃;88%
4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

dimethylbiguanide
657-24-9

dimethylbiguanide

N-(4-hydroxybenzylidene)metformin

N-(4-hydroxybenzylidene)metformin

Conditions
ConditionsYield
With acetic acid In ethanol at 78℃; for 6h;91%
With acetic acid In ethanol at 78℃;88%
dimethylbiguanide
657-24-9

dimethylbiguanide

Ethanesulfonyl chloride
594-44-5

Ethanesulfonyl chloride

N-(ethylsulfonyl)metformin

N-(ethylsulfonyl)metformin

Conditions
ConditionsYield
With potassium hydroxide In acetone at 20℃;91%
With potassium hydroxide In acetonitrile at 20℃; Inert atmosphere;72%
dimethylbiguanide
657-24-9

dimethylbiguanide

cyclohexanesulfonyl chloride
4837-38-1

cyclohexanesulfonyl chloride

N-(cyclohexanesulfonyl)metformin

N-(cyclohexanesulfonyl)metformin

Conditions
ConditionsYield
With potassium hydroxide In acetone at 20℃;91%
With potassium hydroxide In acetonitrile at 20℃; Inert atmosphere;82%
succinic acid anhydride
108-30-5

succinic acid anhydride

dimethylbiguanide
657-24-9

dimethylbiguanide

N-succinylmetformin

N-succinylmetformin

Conditions
ConditionsYield
With potassium hydroxide In acetone at 20℃;91%

Metformin Specification

1. Introduction of Metformin
Metformin is one kind of white or off-white crystal powder. The IUPAC name of 1,1-Dimethylbiguanide is 3-(diaminomethylidene)-1,1-dimethylguanidine. The classification codes are Antidiabetic; Drug / Therapeutic Agent; Hypoglycemic agents; Mutation data; Reproductive Effect. When heated to decomposition it emits toxic fumes of NOx. Besides, it is freely soluble as HCl salt.

2. Properties of Metformin
The other characteristics of this product can be summarized as: (1)ACD/LogP: -1.82; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): -3.82; (4)ACD/LogD (pH 7.4): -3.82; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 1; (9)#H bond acceptors: 5; (10)#H bond donors: 5; (11)#Freely Rotating Bonds: 1; (12)Index of Refraction: 1.576; (13)Molar Refractivity: 33.35 cm3; (14)Molar Volume: 100.7 cm3; (15)Polarizability: 13.22×10-24 cm3; (16)Surface Tension: 50.8 dyne/cm; (17)Enthalpy of Vaporization: 46.06 kJ/mol; (18)Vapour Pressure: 0.0929 mmHg at 25°C; (19)Rotatable Bond Count: 2; (20)Tautomer Count: 3; (21)Exact Mass: 129.101445; (22)MonoIsotopic Mass: 129.101445; (23)Topological Polar Surface Area: 91.5; (24)Heavy Atom Count: 9; (25)Complexity: 132.

3. Structure Descriptors of Metformin
People can use the following data to convert to the molecule structure.
(1)SMILES:[N@H]=C(\N=C(/N)N)N(C)C
(2)InChI:InChI=1/C4H11N5/c1-9(2)4(7)8-3(5)6/h1-2H3,(H5,5,6,7,8)
(3)InChIKey:XZWYZXLIPXDOLR-UHFFFAOYAB
(4)Canonical SMILES : CN(C)C(=N)N=C(N)N

4. Toxicity of Metformin
The following are the toxicity data which has been tested.

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
frog LD50 parenteral 5gm/kg (5000mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Archiwum Immunologii i Terapii Doswiadczalnej. Vol. 2, Pg. 1, 1954.
guinea pig LD50 subcutaneous 146mg/kg (146mg/kg)   Medicina Experimentalis. Vol. 8, Pg. 237, 1963.
man TDLo oral 321mg/kg/15D- (321mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

BLOOD: "CHANGES IN SERUM COMPOSITION (E.G., TP, BILIRUBIN, CHOLESTEROL)"		 New England Journal of Medicine. Vol. 339, Pg. 1860, 1998.
 
mouse LD50 intraperitoneal 247mg/kg (247mg/kg)   Journal of Medicinal Chemistry. Vol. 10, Pg. 521, 1967.
mouse LD50 oral 1450mg/kg (1450mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 9, Pg. 759, 1967.
mouse LD50 subcutaneous 230mg/kg (230mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES		 Archiwum Immunologii i Terapii Doswiadczalnej. Vol. 2, Pg. 1, 1954.
women TDLo oral 191mg/kg/9D-I (191mg/kg) LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA		 Postgraduate Medical Journal. Vol. 76, Pg. 125, 2000.
 

5. Physical Properties of Metformin

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) -2.640 (none)   EST
Atmospheric OH Rate Constant 1.53E-10 cm3/molecule-sec 25 EST

6. Uses of Metformin
Metformin is a biguanide hypoglycemic agent used in the treatment of non-insulin-dependent diabetes mellitus not responding to dietary modification. Metformin improves glycemic control by improving insulin sensitivity and decreasing intestinal absorption of glucose. It can react with imidazo[1,2-a]pyridine-2-carboxylic acid ethyl ester to get 6-imidazo[1,2-a]pyridin-2-yl-N,N-dimethyl-[1,3,5]triazine-2,4-diamine. This reaction needs reagent sodium methoxide and solvent methanol. The yield is 36%.

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