| Identification | More | [Name]
Methimazole | [CAS]
60-56-0 | [Synonyms]
1,3-DIHYDRO-1-METHYL-2H-IMIDAZOL-2-THIONE
1-METHYL-1H-IMIDAZOLE-2-THIOL
1-METHYL-2-IMIDAZOLETHIOL
1-METHYL-2-MERCAPTOIMIDAZOLE
1-METHYLIMIDAZOLE-2-THIOL
2-MERCAPTO-1-METHYLIMIDAZOLE
2-METHOXYCARBONYLAMINO-5-ISOPROPYLTHIO-1 H-BENZIMIDAZOLE
AKOS BBS-00004622
LABOTEST-BB LT00033517
METAZOLE
METHIAZOLE
METHIMAZOL
METHIMAZOLE
TAPAZOLE
THIAMAZOLE
1,3-dihydro-1-methyl-2h-imidazole-2-thion
1,3-dihydro-1-methyl-2H-Imidazole-2-thione
1-methyl-2-mercapto-imidazol
1-methyl-imidazole-2-thio
1-Metylo 2 merkaptoimidazolem | [EINECS(EC#)]
200-482-4 | [Molecular Formula]
C4H6N2S | [MDL Number]
MFCD00179321 | [Molecular Weight]
114.17 | [MOL File]
60-56-0.mol |
| Chemical Properties | Back Directory | [Appearance]
White Solid | [Melting point ]
144-147 °C (lit.) | [Boiling point ]
280 °C | [density ]
1.176 (estimate) | [refractive index ]
1.5000 (estimate) | [Fp ]
280°C | [storage temp. ]
2-8°C | [solubility ]
200g/l | [form ]
Crystalline Powder | [pka]
12.37±0.50(Predicted) | [color ]
White to slightly cream or pale buff | [Water Solubility ]
soluble | [Usage]
Methimazole is a thiourea antithyroid agent that prevents iodine organification, thus inhibiting the synthesis of thyroxine. Antihyperthyroid | [Detection Methods]
HPLC,NMR | [Merck ]
14,5971 | [BRN ]
108646 | [CAS DataBase Reference]
60-56-0(CAS DataBase Reference) | [IARC]
3 (Vol. 79) 2001 | [NIST Chemistry Reference]
Methimazole(60-56-0) | [EPA Substance Registry System]
60-56-0(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R43:May cause sensitization by skin contact.
R62:Possible risk of impaired fertility.
R63:Possible risk of harm to the unborn child. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S27:Take off immediately all contaminated clothing .
S36:Wear suitable protective clothing .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S36/37:Wear suitable protective clothing and gloves . | [WGK Germany ]
3
| [RTECS ]
NI8615000
| [TSCA ]
Yes | [HS Code ]
29332990 | [Safety Profile]
Poison by
subcutaneous route. Moderately toxic by
ingestion and intraperitoneal routes. Human
teratogenic effects. An experimental
teratogen. Experimental reproductive
effects. Questionable carcinogen with
experimental neoplastigenic data. Human
mutation data reported. An antithyroid drug.
When heated to decomposition it emits very
toxic fumes of NOx and SOx. See also
MERCAPTANS. | [Hazardous Substances Data]
60-56-0(Hazardous Substances Data) |
| Hazard Information | Back Directory | [Originator]
Favistan ,Asta | [Definition]
ChEBI: Methimazole is a member of the class of imidazoles that it imidazole-2-thione in which a methyl group replaces the hydrogen which is attached to a nitrogen. It has a role as an antithyroid drug. | [Manufacturing Process]
2 Methods of preparation of thiamazole:
1. To 2,2-diethoxyethylamine methylisothiocyanate was added and mixed after then 1-(2,2-diethoxy-ethyl)-3-methylthiourea was obtained.
The reaction of the 1-(2,2-diethoxyethyl)-3-methylthiourea with sulfuric acid yield thiamazole.
2. 1,1-Diethoxyethane was treated by bromine in the presence CaCO3 and 2- bromo-1,1-diethoxyethane was obtained.
Then to the 2-bromo-1,1-diethoxyethane methylamine was added, mixed and reaction mixture was heated to 120°-130°C in autoclave. As the result (2,2- diethoxyethyl)methylamine was obtained.
(2,2-Diethoxyethyl)methylamine reacted with potassium thiocyanate in the presence of hydrochloric acid and give the thiamazole, yellow crystallic precipitate, melting point 144°-147°C. | [Brand name]
Tapazole (Jones);
Tapazole (King)
. | [Therapeutic Function]
Thyroid inhibitor | [General Description]
Methimazole, 1-methylimidazole-2-thiol (Tapazole), occurs as a white to off-white, crystallinepowder with a characteristic odor and is freely soluble inwater. A 2% aqueous solution has a pH of 6.7 to 6.9. It shouldbe packaged in well-closed, light-resistant containers. | [Biochem/physiol Actions]
Methimazole is a thiourea antithyroid agent that prevents iodine organification, thus inhibiting the synthesis of thyroxine. | [Clinical Use]
Methimazole is indicated in the treatment of hyperthyroidism.It is more potent than propylthiouracil. The side effectsare similar to those of propylthiouracil. As with otherantithyroid drugs, patients using this drug should be undermedical supervision. Also, like the other antithyroid drugs,methimazole is most effective if the total daily dose is subdividedand given at 8-hour intervals. | [Synthesis]
Methimazole, 1-methyl-2-imidazolthiol (25.2.5), is synthesized by reacting
aminoacetic aldehyde diethylacetal with methylisothiocyanate and subsequent hydrolysis
of the acetal group of the resulting disubstituted urea derivative 25.2.4 by a solution
of sulfuric acid, during which a simultaneous cyclization reaction takes place, forming the
imidazole ring of the desired methimazole .
| [Veterinary Drugs and Treatments]
Methimazole is considered by most clinicians to be the agent
of choice when using drugs to treat feline hyperthyroidism.
Propylthiouracil has significantly higher incidences of adverse
reactions
when compared to methimazole and is rarely used today.
Transdermal methimazole (in PLO gel; 2.5 mg twice daily) has been
used with some therapeutic success in cats that do not tolerate oral
dosing. Efficacy may require four or more weeks to detect. Studies
are ongoing.
Methimazole appears to be useful for the prophylactic prevention
of cisplatin induced nephrotoxicity in dogs. | [Purification Methods]
Crystallise it from EtOH. UV: at 251nm (H2O), 260nm (EtOH) and 267nm (CHCl3). [Lawson max & Morley J Chem Soc 1103 1956, Beilstein 24 H 17, 24 III/IV 61.] |
| Questions And Answer | Back Directory | [description]
Methimazole is an antithyroid medication used in the therapy of hyperthyroidism and Graves disease. It works by making it harder for the body to make thyroid hormone.
It is also known as thiamazole, is a thioamide and a thyroid hormone antagonist which acts by inhibiting the incorporation of iodine into tyrosyl residues of thyroglobulin and, thus, lowering thyroid hormone levels.
It resembles propylthiouracil both in chemical structure and activity.
Methimazole is primarily used for the treatment of hyperthyroidism, by inhibiting the peroxidase system, hindering thyroxine (T4) and tri-triiodothyronine (T3) synthesis, animal experiments show that it can inhibit B lymphocytes synthesizing antibodies, and reduce levels of thyroid stimulating antibodies in blood circulating it can make suppressing T cell function return to normal, it is applicable to hyperthyroidism caused by a variety of factors . Like other various drugs (propylthiouracil), it also has some adverse reactions while it is taken, Including hematologic adverse reactions, primarily neutropenia, hematopoietic dysfunction or disorder, thrombocytopenia, reduction of prothrombin or factor VII ; long-term medication can also cause liver damage,such as cholestatic jaundice and toxic hepatitis ; other skin reactions such as hair loss, itching, rash, dermatitis, lupus erythematosus, as well as some other rare adverse reactions. Also methimazole allows prothrombin time to prolong , and increases serum alkaline phosphatase, aspartate aminotransferase (AST) and alanine aminotransferase (ALT)and causes blood bilirubin and blood lactate dehydrogenase increasing. Therefore, patients in the medication should regularly take blood tests, liver function tests and peripheral blood leukocytes.
The above information is edited by the Chemicalbook of Tian Ye. | [Chemical properties]
leaf-shaped crystalline (ethanol), melting point 146-148 ℃, boiling point 280 ℃ (decomposition), soluble in water, soluble in alcohol, chloroform, slightly soluble in ether, benzene.
| [Uses]
Carbimazole intermediates.
anti-thyroid drugs.
| [Production methods]
React amino acetal with methyl isothiocyanate to genarate this product. The product can also be produced from thiocyanate and N-substituted amino acetal.
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