60-56-0 Usage
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 lookchem 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
Different sources of media describe the Uses of 60-56-0 differently. You can refer to the following data:
1. Carbimazole intermediates.
anti-thyroid drugs.
2. Methimazole also directly disrupts thyroxine and triiodothyronin sysnthesis in the thyroid
gland, and it is used for the same indications as propylthiouracil and methylthiouracil to
treat hyperfunctioning thyroid glands in patients with Basedow’s disease.
3. Methimazole is a thiourea antithyroid agent that prevents iodine organification, thus inhibiting the synthesis of thyroxine. Antihyperthyroid
4. 2-Mercapto-1-methylimidazole was employed as hydrophobic charge-induction chromatography ligand for antibody purification. It was also used in preparation of nitrile functionalized methimazole-based room temperature ionic liquids.
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.
Chemical Properties
White Solid
Originator
Favistan ,Asta
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)
.
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.
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.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 60-56-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 0 respectively; the second part has 2 digits, 5 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 60-56:
(4*6)+(3*0)+(2*5)+(1*6)=40
40 % 10 = 0
So 60-56-0 is a valid CAS Registry Number.
InChI:InChI=1/C4H6N2S/c1-6-3-2-5-4(6)7/h2-3H,1H3,(H,5,7)
60-56-0Relevant articles and documents
new synthetic process for thiamazole
-
Paragraph 0042-0045, (2021/05/04)
The present invention relates to a novel synthesis method capable of synthesizing thiamazole by simple heat treatment of methylimidazole and S_8. The present invention provides a safe and low-cost method for synthesizing thiamazole.
Oxidant/complexing properties of the methimazole (MeImHS)/iodine system towards palladium and gold metals. Crystal structure of the complex cation [PdII(MeImHS)4]2+ balanced by a tetraiodide/iodide mixture
Isaia, Francesco,Aragoni, Maria Carla,Arca, Massimiliano,Caltagirone, Claudia,Castellano, Carlo,Demartin, Francesco,Garau, Alessandra,Lippolis, Vito,Pivetta, Tiziana
, p. 2652 - 2660 (2020/02/20)
This paper reports on the oxidative dissolution ability in dichloromethane and water of the methimazole-iodine system towards gold and palladium in powder. This research has a potential application in the recovery process of these metals from electrical and electronic waste equipment (WEEE). The iodine-adduct of methimazole (1-methyl-3H-imidazole-2-thione; MeImHS) oxidises gold and palladium powders in dichloromethane to form the complexes [AuI(MeImHS)2]I3 and [PdII(MeImHS)4](I4)0.73·2(I)0.27. The X-ray crystal structure of the palladium complex shows a square-planar Pd(ii) ion S-coordinated to four MeImHS units with the charge essentially balanced by an unusual tetraiodide I42- with minor amounts of iodide. The oxidative dissolution of palladium in water medium produces the cation [PdII(MeImHS)4]2+. Considering the reaction conditions under which the process was performed ([I2] = 1.14 × 10-3 M, T = 20 °C, pH = 5, reaction time 24 h), the obtained value of 64% of oxidation yields from Pd(0) to Pd(ii) is to be considered satisfactory. No appreciable oxidation was observed for the gold powder in water. The feasibility of recovering palladium from the triiodide salt of the complex cation [PdII(MeImHS)4]2+ was verified by carrying out a two-step reduction process using magnesium powder.
A 2 - mercapto - 1 - alkyl imidazole of preparation method (by machine translation)
-
Paragraph 0024; 0027; 0030; 0033, (2018/01/19)
The invention discloses a 2 - mercapto - 1 - alkyl imidazole synthesis method, which belongs to the technical field of organic synthesis. Imidazole and alkyl halide in the presence of an inorganic base sealing reaction the temperature of the 1 - alkyl imidazole, then dissolved in ether in the solvent, the low temperature by adding 1 - 1.1 equivalent BuLi, then adding 0.9 - 0.95 equivalent powder reflux reaction, after cooling add acetyl chloride to obtain 2 - acetyl thio - 1 - alkyl imidazole; the final 2 - acetyl thio - 1 - alkyl imidazole dissolved in alcohol solvent, adding a catalytic amount of hydrogen chloride or potassium carbonate deprotection, to obtain 2 - mercapto - 1 - alkyl imidazole. The raw material of the invention is cheap, and more friendly to the environment, the advantages of easy operation, the quality of the product in accordance with the electronic chemicals using standard. (by machine translation)
