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Home> Encyclopedia >   /  Endocrine System Agents  /  Pharmaceutical Intermediates  /  Pharmaceutical  /  Organic Intermediate  /  Organic Intermediates
Methimazole structure
Methimazole structure

Methimazole

Iupac Name:3-methyl-1H-imidazole-2-thione
CAS No.:60-56-0
Molecular Weight:114.16900
Introduction: 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. View more+
1. Names and Identifiers
1.1 Name
Methimazole
1.2 Synonyms

1-Methyl-1,3-dihydro-2H-imidazole-2-thione 1-methyl-1H-imidazole-2(3H)-thione 1-methyl-1H-imidazole-2-thiol 1-Methyl-2-mercapto-1H-imidazole 1-methyl-2-mercapto-imidazole 1-Methyl-4-imidazoline-2-thione 1-methylimidazole-2-thione 2H-Imidazole-2-thione, 1,3-dihydro-1-methyl- 2-Mercapto-1-methyl-1H-imidazole 2-Mercapto-1-methylimidazole 2-mercapto-1-methyl-imidazole 3-methyl-imidazole-2-thione Basolan EINECS 200-482-4 Favistan Frentirox mercaptomethylimidazole Mercazole Merkastan METAZOLE Metazolo Methiamazole Methimazol methyl-2-mercaptoimidazole Metizol MFCD00179321 N-METHYLIMIDAZOLETHIOL Tapazole Tapuzole thiamazole Thimazol thioimidazole Thymidazole

1.3 CAS No.
60-56-0
1.4 CID
1349907
1.5 EINECS(EC#)
200-482-4
1.6 Molecular Formula
C4H6N2S (isomer)
1.7 Inchi
InChI=1S/C4H6N2S/c1-6-3-2-5-4(6)7/h2-3H,1H3,(H,5,7)
1.8 InChkey
PMRYVIKBURPHAH-UHFFFAOYSA-N
1.9 Canonical Smiles
CN1C=CNC1=S
1.10 Isomers Smiles
CN1C=CNC1=S
2. Properties
3.1 Density
1.28 g/cm3
3.1 Melting point
144-147°C(lit.)
3.1 Boiling point
280 °C
3.1 Refractive index
1.5000 (estimate)
3.1 Flash Point
280°C
3.1 Precise Quality
114.02500
3.1 PSA
56.62000
3.1 logP
0.70880
3.1 Solubility
200g/l
3.2 Appearance
White Solid
3.3 Color/Form
LEAFLETS FROM ALCOHOL
WHITE TO PALE BUFF, CRYSTALLINE SUBSTANCE; STARCH-LIKE IN APPEARANCE & TO TOUCH
3.4 pKa
12.37±0.50(Predicted)
3.5 Water Solubility
soluble
3.6 Spectral Properties
MAX ABSORPTION (CHLOROFORM): 267 NM (LOG E= 4.23)
IR: 2:1062C (Aldrich Library of Infrared Spectra, Aldrich Chemical Co, Milwaukee, WI)
UV: 3-18 (Organic Electronic Spectral Data, Phillips et al, John Wiley & Sons, New York)
NMR: 8:30A (Aldrich Library of Mass Spectra, Aldrich Chemical Co, Milwaukee, WI)
UV max (0.1 N sulfuric acid): 211, 251.5 nm (E 593, 1528, 1%, 1cm).
3.7 StorageTemp
Refrigerator
3. Use and Manufacturing
4.1 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.
4.2 Produe Method
React amino acetal with methyl isothiocyanate to genarate this product. The product can also be produced from thiocyanate and N-substituted amino acetal.
4.3 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.] Methimazole Preparation Products And Raw materials Raw materials
4.4 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.
4.5 Storage
Ambient temperatures.
4.6 Usage
Carbimazole intermediates.anti-thyroid drugs.
4. Safety and Handling
5.1 Symbol
GHS07, GHS08
5.1 Hazard Codes
Xn
5.1 Signal Word
Warning
5.1 Risk Statements
R43; R62; R63
5.1 Safety Statements
S26-S27-S36-S45-S36/37
5.1 Exposure Standards and Regulations
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
5.2 Octanol/Water Partition Coefficient
log Kow = -0.34
5.3 Hazard Declaration
H317-H361
5.3 DisposalMethods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
5.4 RIDADR
NONH for all modes of transport
5.4 Caution Statement
P280
5.4 Formulations/Preparations
...METHIMAZOLE, USP (1-METHYL-2-MERCAPTOIMIDAZOLE; TAPAZOLE), MARKETED IN 5- & 10-MG TABLETS.
5.5 WGK Germany
3
5.5 RTECS
NI8615000
5.5 Protective Equipment and Clothing
Rashes may follow high doses of methimazole (120 mg daily). Both major (agranulocytosis, hepatotoxicity) and minor (arthralgias, skin rash, gastric intolerance) adverse effects are not dose related.
5.6 Report

Reported in EPA TSCA Inventory.

5.7 Skin, Eye, and Respiratory Irritations
Rashes may follow high doses of methimazole (120 mg daily). Both major (agranulocytosis, hepatotoxicity) and minor (arthralgias, skin rash, gastric intolerance) adverse effects are not dose related.
5.8 Safety

Hazard Codes:?Xn
Risk Statements: 43-62-63
43: May cause sensitization by skin contact
62: Possible risk of impaired fertility
63: Possible risk of harm to the unborn child
Safety Statements: 26-27-45-36/37
26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
27: Take off immediately all contaminated clothing
45: In case of accident or if you feel unwell, seek medical advice immediately (show label where possible)
36/37: Wear suitable protective clothing and gloves
WGK Germany: 3
RTECS: NI8615000
HS Code: 29332990
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.

5.9 Specification

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam.?
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Avoid ingestion and inhalation. Use only in a chemical fume hood.
Storage: Store in a cool, dry place. Store in a tightly closed container.

5.10 Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 500mg/kg (500mg/kg) ? National Technical Information Service. Vol. AD277-689,
mouse LD50 oral 860mg/kg (860mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR
Arzneimittel-Forschung. Drug Research. Vol. 4, Pg. 20, 1954.
mouse LD50 subcutaneous 345mg/kg (345mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR
Arzneimittel-Forschung. Drug Research. Vol. 4, Pg. 20, 1954.
rat LD50 oral 2250mg/kg (2250mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: TREMOR
Arzneimittel-Forschung. Drug Research. Vol. 4, Pg. 20, 1954.
rat LD50 subcutaneous 1050mg/kg (1050mg/kg) ? Farmaco, Edizione Scientifica. Vol. 14, Pg. 54, 1959.
women TDLo oral 13mg/kg/33D-I (13mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EAR

BEHAVIORAL: EXCITEMENT

GASTROINTESTINAL: OTHER CHANGES
Clinical Endocrinology Vol. 51, Pg. 667, 1999.
women TDLo oral 492mg/kg/88W- (492mg/kg) ENDOCRINE: CHANGE IN GONADOTROPINS

BLOOD: AGRANULOCYTOSIS
Netherlands Journal of Medicine. Vol. 43, Pg. 71, 1993.

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin sensitization, Category 1

Reproductive toxicity, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H317 May cause an allergic skin reaction

H361 Suspected of damaging fertility or the unborn child

Precautionary statement(s)
Prevention

P261 Avoid breathing dust/fume/gas/mist/vapours/spray.

P272 Contaminated work clothing should not be allowed out of the workplace.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P201 Obtain special instructions before use.

P202 Do not handle until all safety precautions have been read and understood.

Response

P302+P352 IF ON SKIN: Wash with plenty of water/...

P333+P313 If skin irritation or rash occurs: Get medical advice/attention.

P321 Specific treatment (see ... on this label).

P362+P364 Take off contaminated clothing and wash it before reuse.

P308+P313 IF exposed or concerned: Get medical advice/ attention.

Storage

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

7. Other Information
7.0 Usage
Possesses antioxidant properties
8. Computational chemical data
  • Molecular Weight:114.16900g/mol
  • Molecular Formula:C4H6N2S
  • Compound Is Canonicalized:True
  • XLogP3-AA:
  • Exact Mass:114.02516937
  • Monoisotopic Mass:114.02516937
  • Complexity:119
  • Rotatable Bond Count:0
  • Hydrogen Bond Donor Count:1
  • Hydrogen Bond Acceptor Count:1
  • Topological Polar Surface Area:47.4
  • Heavy Atom Count:7
  • Defined Atom Stereocenter Count:0
  • Undefined Atom Stereocenter Count:0
  • Defined Bond Stereocenter Count:0
  • Undefined Bond Stereocenter Count:0
  • Isotope Atom Count:0
  • Covalently-Bonded Unit Count:1
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