Methimazole

Base Information

• Chemical Name: Methimazole
• CAS No.: 60-56-0
• Deprecated CAS: 4708-61-6,85916-84-3,85916-84-3
• Molecular Formula: C4H6N2S
• Molecular Weight: 114.171
• Hs Code.: 29332990
• European Community (EC) Number: 200-482-4
• NSC Number: 757111,38608
• UNII: 554Z48XN5E
• DSSTox Substance ID: DTXSID4020820
• Nikkaji Number: J1.400A
• Wikipedia: Thiamazole,Methimazole
• Wikidata: Q419663
• NCI Thesaurus Code: C641
• RXCUI: 6835
• Pharos Ligand ID: 1LULL914TSBR
• Metabolomics Workbench ID: 43060
• ChEMBL ID: CHEMBL1515
• Mol file: 60-56-0.mol

Synonyms:1 Methyl 2 mercaptoimidazole;1-Methyl-2-mercaptoimidazole;Favistan;Henning, Thiamazol;Hexal, Thiamazol;Mercasolyl;Mercazol;Mercazole;Mercazolyl;Merkazolil;Methimazole;Methizol;Methylmercaptoimidazole;Methymazol;Metisol;Metizol;Strumazol;Tapazole;Thiamazol Henning;Thiamazol Hexal;Thiamazole;Thimazol;Thyrozol;Tiamazol;Tirodril

Chemical Property of Methimazole

Chemical Property:

• Appearance/Colour: White Solid
• Melting Point: 144-147 °C(lit.)
• Refractive Index: 1.5000 (estimate)
• Boiling Point: 154.8 °C at 760 mmHg
• PKA: 12.37±0.50(Predicted)
• Flash Point: 47.4 °C
• PSA: 56.62000
• Density: 1.28 g/cm³
• LogP: 0.70880
• Storage Temp.: Refrigerator
• Solubility.: 200g/l
• Water Solubility.: soluble
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 114.02516937
• Heavy Atom Count: 7
• Complexity: 119

Purity/Quality:

99% ^*data from raw suppliers

Methimazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 43-62-63-22
• Safety Statements: 26-27-36-45-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Drug Classes: Antithyroid Agents
• Canonical SMILES: CN1C=CNC1=S
• Recent ClinicalTrials: Methimazole in Patients With Progressive Glioblastoma
• Recent EU Clinical Trials: Assessing the feasibility of pharmacologically induced hypothyroidism in patients with advanced pancreatic cancer - a pilot study
• Recent NIPH Clinical Trials: A prospective randomized control study of combination therapy with low-dose methimazole and a cholesterol absorption inhibitor as for the initial treatment of childhood-onset Graves disease
• 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.
• Uses: Carbimazole intermediates. anti-thyroid drugs. 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. Methimazole is a thiourea antithyroid agent that prevents iodine organification, thus inhibiting the synthesis of thyroxine. Antihyperthyroid 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.
• 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.

Technology Process of Methimazole

There total 27 articles about Methimazole which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.2%

N-methylaminoacetaldehyde diethyl acetal (20677-73-0) → 1-methyl-1,3-dihydro-imidazole-2-thione (60-56-0,223768-14-7,4708-61-6)

Guidance literature:

With ammonium thiocyanate; hydrogenchloride; tetrabutylammomium bromide; In water; at 40 - 60 ℃; for 7h; Reagent/catalyst; Temperature;

Reference yield: 91.0%

2-tert-butylthio-1-methyl-1H-imidazole (79487-94-8) → 2-Mercapto-1-methylimidazole (60-56-0)

Guidance literature:

With aluminum (III) chloride; at 20 ℃; Reagent/catalyst; Inert atmosphere;

Reference yield: 82.54%

1-methyl-1H-imidazole (616-47-7) → 2-Mercapto-1-methylimidazole (60-56-0)

Guidance literature:

1-methyl-1H-imidazole; With n-butyllithium; In tetrahydrofuran; hexane; at -10 ℃; for 1.5h;

With sulfur; In tetrahydrofuran; hexane; for 9h; Temperature; Reflux;

upstream raw materials:

(2-mercapto-3-methylimidazol-4-yl)methanoic acid

2,2-diethoxy-ethanamine

methyl thioisocyanate

potassium thioacyanate

Downstream raw materials:

2-(prop-2-enylsulfanyl)-1-methyl-1H-imidazole

1-methyl-2-[(4-nitrophenyl)thio]-1H-imidazole

1-methyl-2-(4-nitro-benzylsulfanyl)-1H-imidazole

2-[(3,4-Dimethoxyphenyl)thio]-1-methyl-1H-imidazole hydrochloride

Refernces

• 1、 Isaia, Francesco,Aragoni, Maria Carla,Arca, Massimiliano,Caltagirone, Claudia,Castellano, Carlo,Demartin, Francesco,Garau, Alessandra,Lippolis, Vito,Pivetta, Tiziana. "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". . p. 2652 - 2660. Retrieved 2020/02/20.
• 2、 -. "Methimazole synthesizing and purifying method". Paragraph 0005; 0021; 0024; 0026-0028. . Retrieved 2017/10/07.