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61-68-7

Basic Information
CAS No.: 61-68-7
Name: Mefenamic acid
Article Data: 53
Molecular Structure:
Molecular Structure of 61-68-7 (Mefenamic acid)
Formula: C15H15NO2
Molecular Weight: 241.29
Synonyms: Acido mefenamico;Acido mefenamico [INN-Spanish];Acidum mefenamicum;Acidum mefenamicum [INN-Latin];Anthranilic acid, N-2,3-xylyl;Bafhameritin-M;Benzoic acid, 2-((2,3-dimethylphenyl)amino)-;Bonabol;Fenamin;HL 1;Lysalgo;Mefacit;Mefedolo;Rolan;Ponstan forte;Ponalar;Parkemed;Namphen;N-(2,3-Xylyl)-2-aminobenzoic acid;Mycasaal;
EINECS: 200-513-1
Density: 1.203 g/cm3
Melting Point: 230 °C
Boiling Point: 398.8 °C at 760 mmHg
Flash Point: 195 °C
Solubility: It is soluble in acetone, chloroform, dichloromethane, methanol. Insoluble in water.
Appearance: light yellow solid
Hazard Symbols: HarmfulXn
Risk Codes: 22-40-20/21/22
Safety: 22-36
PSA: 49.33000
LogP: 3.81820
Synthetic route

mefenamic acid benzyl ester

61-68-7

mefenamic Acid

Conditions
ConditionsYield
With hydrogen In methanol at 50℃; under 3750.38 Torr; Flow reactor; chemoselective reaction;98%
87-59-2

2,3-Dimethylaniline

118-91-2

ortho-chlorobenzoic acid

61-68-7

mefenamic Acid

Conditions
ConditionsYield
Stage #1: ortho-chlorobenzoic acid With sodium carbonate In N,N-dimethyl-formamide at 80℃; for 0.5h;
Stage #2: 2,3-Dimethylaniline With manganese(II) acetate In water; N,N-dimethyl-formamide; toluene at 120 - 130℃; Reagent/catalyst;
94.8%
Stage #1: ortho-chlorobenzoic acid With sodium carbonate In N,N-dimethyl-formamide at 80℃; for 1.16667h;
Stage #2: 2,3-Dimethylaniline With copper In water; N,N-dimethyl-formamide; toluene at 104 - 123℃;
91.3%
With copper; sodium carbonate In N,N-dimethyl-formamide at 140℃; for 2h;90%
88-67-5

2-Iodobenzoic acid

87-59-2

2,3-Dimethylaniline

61-68-7

mefenamic Acid

Conditions
ConditionsYield
With sodium acetate; copper (I) acetate In water for 1.5h; Heating;93%
With copper; potassium carbonate In N,N-dimethyl-formamide at 100℃; for 12h; Schlenk technique; Inert atmosphere;
13481-67-9

2-[(2,3-dimethylphenyl)amino]benzonitrile

61-68-7

mefenamic Acid

Conditions
ConditionsYield
With methanol; potassium hydroxide In water at 100℃; for 12h; Schlenk technique;91%
With water; potassium hydroxide In methanol for 12h; Reflux;
With water; potassium hydroxide In ethanol at 95℃; for 20h; Inert atmosphere;161 mg

2-((2,3-dimethylphenyl)amino)-N-(quinolin-8-yl)benzamide

61-68-7

mefenamic Acid

Conditions
ConditionsYield
With potassium hydroxide In ethanol at 110℃; for 18h; Sealed tube;90%
1488-42-2

Diphenyliodonium-2-carboxylate

87-59-2

2,3-Dimethylaniline

61-68-7

mefenamic Acid

Conditions
ConditionsYield
With copper diacetate In isopropyl alcohol for 23h; Heating;54%
With copper diacetate In isopropyl alcohol at 85℃; for 23h;54%
copper diacetate In isopropyl alcohol at 80℃; for 15h;90 % Spectr.
873-32-5

2-Chlorobenzonitrile

87-59-2

2,3-Dimethylaniline

61-68-7

mefenamic Acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: Pd-PEPPSI-IPrAn; caesium carbonate / 1,4-dioxane / 24 h / 80 °C / Inert atmosphere
2: water; potassium hydroxide / methanol / 12 h / Reflux
View Scheme

mefenamic acid

A

103-90-2

4-acetaminophenol

B

61-68-7

mefenamic Acid

Conditions
ConditionsYield
With hydrogenchloride; water pH=2; Kinetics; Solvent; Reagent/catalyst;
87-59-2

2,3-Dimethylaniline

61-68-7

mefenamic Acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrahydrofuran; diethyl ether / 0 - 20 °C
2: cesium fluoride / tetrahydrofuran / 16 h / 70 °C / Inert atmosphere
3: potassium hydroxide; methanol / water / 12 h / 100 °C / Schlenk technique
View Scheme
55591-34-9

N-(2,3-dimethylphenyl)cyanamide

61-68-7

mefenamic Acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: cesium fluoride / tetrahydrofuran / 16 h / 70 °C / Inert atmosphere
2: potassium hydroxide; methanol / water / 12 h / 100 °C / Schlenk technique
View Scheme
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    Specifications CAS No.: 61-68-7 Other Names: Mefenamic Acid MF: C15H15NO2 EINECS No.: 200-513-1 Place of Origin: China (Mainland)

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    Product Name: Mefenamic acid Synonyms: Mefenamic Acid (200 mg);N-(2,3-Dimethylphenyl)anthranilic Acid 2-(2,3-Dimethylphenylamino)benzoic Acid 2-(2,3-Xylidino)benzoic Acid;2’,3’-dimethyl-2-diphenylaminecarboxylicaci;MefenaMic Aicd (API

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Chemistry

Molecular structure of Mefenamic acid (CAS NO.61-68-7) is:

Product Name: Mefenamic acid
CAS Registry Number: 61-68-7
IUPAC Name: 2-(2,3-Dimethylanilino)benzoic acid
Molecular Weight: 241.2851 [g/mol]
Molecular Formula: C15H15NO2
XLogP3: 5.1
H-Bond Donor: 2
H-Bond Acceptor: 3
EINECS: 200-513-1
Melting Point: 230 °C
Surface Tension: 51.7 dyne/cm
Density: 1.203 g/cm3
Flash Point: 195 °C
Enthalpy of Vaporization: 68.49 kJ/mol
Boiling Point: 398.8 °C at 760 mmHg
Vapour Pressure: 4.45E-07 mmHg at 25°C 
Product Categories: Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts; Amino Acids 13C, 2H, 15N; Amino Acids & Derivatives; Intermediates & Fine Chemicals; Pharmaceuticals; API's

Uses

  Mefenamic acid (CAS NO.61-68-7) is a non-steroidal anti-inflammatory drug, so it can be used to treat pain, including menstrual pain, also ot is typically prescribed for oral administration. However, it decreases inflammation (swelling) and uterine contractions by a still unknown mechanism and it is thought to be related to the inhibition of prostaglandin synthesis.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 intravenous 100mg/kg (100mg/kg)   Current Medical Research and Opinion. Vol. 4, Pg. 17, 1976.
man TDLo oral 14285ug/kg/3D (14.285mg/kg)   British Journal of Clinical Practice. Vol. 49, Pg. 161, 1995.
man TDLo oral 14285ug/kg/3D (14.285mg/kg)   British Journal of Clinical Practice. Vol. 49, Pg. 161, 1995.
man TDLo oral 257mg/kg/12D- (257mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" British Medical Journal. Vol. 291, Pg. 661, 1985.
man TDLo oral 840mg/kg/6W-I (840mg/kg) GASTROINTESTINAL: ULCERATION OR BLEEDING FROM LARGE INTESTINE

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
British Medical Journal. Vol. 287, Pg. 1626, 1983.
mouse LD50 intramuscular 400mg/kg (400mg/kg)   Pharmaceutical Chemistry Journal Vol. 17, Pg. 353, 1983.
mouse LD50 intraperitoneal 120mg/kg (120mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 19, Pg. 36, 1969.
mouse LD50 intravenous 96mg/kg (96mg/kg)   Yakugaku Zasshi. Journal of Pharmacy. Vol. 89, Pg. 1392, 1969.
mouse LD50 oral 525mg/kg (525mg/kg)   Journal de Pharmacologie. Vol. 2, Pg. 259, 1971.
mouse LDLo subcutaneous > 2gm/kg (2000mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1579, 1970.
rat LD50 intraperitoneal 327mg/kg (327mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
rat LD50 intravenous 112mg/kg (112mg/kg)   Current Medical Research and Opinion. Vol. 4, Pg. 17, 1976.
rat LD50 oral 740mg/kg (740mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Toho Igakkai Zasshi. Journal of Medical Society of Toho University. Vol. 28, Pg. 99, 1981.
women LDLo oral 280mg/kg/2W-I (280mg/kg) LIVER: LIVER FUNCTION TESTS IMPAIRED

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"

BLOOD: OTHER HEMOLYSIS WITH OR WITHOUT ANEMIA
Drug Safety. Vol. 6, Pg. 230, 1991.
women TDLo oral 20mg/kg/4D-I (20mg/kg) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF ENDOCRINE PANCREAS Canadian Medical Association Journal. Vol. 126, Pg. 894, 1982.
women TDLo oral 450mg/kg (450mg/kg) SENSE ORGANS AND SPECIAL SENSES: MYDRIASIS (PUPILLARY DILATION): EYE

BEHAVIORAL: TOXIC PSYCHOSIS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
South African Medical Journal. Vol. 67, Pg. 823, 1985.
women TDLo unreported 120mg/kg/4D (120mg/kg) BEHAVIORAL: WITHDRAWAL

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Lancet. Vol. 2, Pg. 745, 1980.

Safety Profile

Safty information about Mefenamic acid (CAS NO.61-68-7) is:
Hazard Codes: HarmfulXn
Risk Statements: 22-40-20/21/22 
R22:Harmful if swallowed. 
R40:Limited evidence of a carcinogenic effect. 
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 22-36
S22:Do not breathe dust. 
S36:Wear suitable protective clothing.
WGK Germany: 3
RTECS: CB4550000

Specification

 Mefenamic acid , its cas register number is 61-68-7. It also can be called Mefenamic acid [USAN:INN:BAN:JAN] ; 2-((2,3-Dimethylphenyl)amino)benzoic acid ; 2-Diphenylaminecarboxylic acid, 2',3'-dimethyl- ; Ac. mefenamico ; Ac. mefenamico [Italian] ; Acide mefenamique ; Acide mefenamique [French] ; Acide mefenamique [INN-French] ; Acido mefenamico ; Acido mefenamico [INN-Spanish] ; Acidum mefenamicum ; Acidum mefenamicum [INN-Latin] ; Anthranilic acid, N-2,3-xylyl- ; Bafhameritin-M ; Benzoic acid, 2-((2,3-dimethylphenyl)amino)- ; Benzoic acid, 2-(2,3-dimethylphenyl)amino- ; Bonabol ; Fenamin ; HL 1 ; Lysalgo ; Mefacit ; Mefedolo ; Mefenamate ; Mefenamic acid ; Mefenaminsaeure ; Mephenamic acid ; Mephenaminic acid ; Methenamic acid ; Mycasaal ; N-(2,3-Dimethylphenyl)anthranilic acid ; N-(2,3-Xylyl)-2-aminobenzoic acid ; N-2,3-Xylylanthranilic acid ; Namphen ; Parkemed ; Ponalar ; Ponstan ; Ponstan forte ; Ponstel ; Rolan ; Tamany Bonsan ; Tanston ; Vialidon . It is a light yellow solid. Since it plays a significant role in mefenamic acid elimination, patients with known liver deficiency may be prescribed lower doses. Kidney deficiency may also cause accumulation of the drug and its metabolites in the excretory system. Therefore patients suffering from renal conditions should not be prescribed mefenamic acid.