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60-56-0 molecular structure
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1-methyl-2,3-dihydro-1H-imidazole-2-thione

ChemBase ID: 643
Molecular Formular: C4H6N2S
Molecular Mass: 114.16884
Monoisotopic Mass: 114.0251692
SMILES and InChIs

SMILES:
S=c1n(cc[nH]1)C
Canonical SMILES:
Cn1cc[nH]c1=S
InChI:
InChI=1S/C4H6N2S/c1-6-3-2-5-4(6)7/h2-3H,1H3,(H,5,7)
InChIKey:
PMRYVIKBURPHAH-UHFFFAOYSA-N

Cite this record

CBID:643 http://www.chembase.cn/molecule-643.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
1-methyl-2,3-dihydro-1H-imidazole-2-thione
IUPAC Traditional name
methimazole
1-methyl-2,3-dihydro-1H-imidazole-2-thione
Brand Name
Basolan
Danantizol
Favistan
Frentirox
Merkastan
Metizol
Metotirin
Strumazol
Strumazole
Tapazole
Tapuzole
Thacapzol
Thycapsol
Thycapzol
Synonyms
Thymidazole
Thymidazol
Thimazole
Thiamazole
Thiamazol
Metothyrine
Metothyrin
Methimazol
Methiamazole
Methamazole
Metazolo
Merkazolil
Mercazolyl
Mercazole
Mercasolyl
Mercaptazole
Methimazole
Methimazole
Thiamazole
1-Methyl-1H-imidazole-2(3H)-thione
Basolan
1-Methyl-1H-imidazole-2-thiol
2-Mercapto-1-methyl-1H-imidazole
1,3-Dihydro-1-methyl-2H-imidazole-2-thione
2-Mercapto-1-methylimidazole
1-Methylimidazole-2-thiol
1-Methyl-2-imidazolethiol
Methimazole
2-Mercapto-1-methylimidazole
1-甲基-2-咪唑硫醇
2-巯基-1-甲基咪唑
甲巯咪唑
甲巯咪唑
2-巯基-1-甲基咪唑
CAS Number
60-56-0
EC Number
200-482-4
MDL Number
MFCD00179321
Beilstein Number
108646
PubChem SID
24882870
160964106
24897266
24858194
46506536
24870159
PubChem CID
1349907
CHEBI ID
50673
ATC CODE
H03BB02
CHEMBL
1515
Chemspider ID
1131173
DrugBank ID
DB00763
KEGG ID
D00401
Unique Ingredient Identifier
554Z48XN5E
Wikipedia Title
Methimazole
Medline Plus
a682464

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 10.411967  H Acceptors
H Donor LogD (pH = 5.5) 0.74566555 
LogD (pH = 7.4) 0.74527997  Log P 0.7456705 
Molar Refractivity 33.2322 cm3 Polarizability 12.8416 Å3
Polar Surface Area 15.27 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -0.38  LOG S -1.0 
Solubility (Water) 1.13e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
2.75 mg/mL (20°C) expand Show data source
275 g/L expand Show data source
Melting Point
143-145 °C expand Show data source
144-147 °C(lit.) expand Show data source
144-147°C expand Show data source
146°C (294.8°F) expand Show data source
146-148 expand Show data source
Boiling Point
280(dec.)°C expand Show data source
Flash Point
>100°C expand Show data source
Hydrophobicity(logP)
-0.2 expand Show data source
Storage Condition
-20°C expand Show data source
Room Temperature (15-30°C) expand Show data source
Storage Warning
Harmful/Irritant/Teratogenic/Stench/Store under Argon expand Show data source
RTECS
NI8615000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
63-43-62 expand Show data source
R:22 expand Show data source
Safety Statements
26-27-36-45 expand Show data source
S:36/37/39 expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H317-H361 expand Show data source
GHS Precautionary statements
P280 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
93% expand Show data source
Excretion
Renal expand Show data source
Half Life
5-6 hours expand Show data source
Metabolism
Hepatic expand Show data source
Protein Bound
None expand Show data source
Legal Status
Rx-only (US) expand Show data source
Pregnancy Category
D (US) expand Show data source
Gene Information
human ... CYP1A2(1544) expand Show data source
Mechanism of Action
Thyroid hormone synthesis inhibitor expand Show data source
Purity
≥97.0% (S) expand Show data source
≥99% expand Show data source
95+% expand Show data source
98% expand Show data source
Grade
analytical standard expand Show data source
purum expand Show data source
VETRANAL™, analytical standard expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Antithyroid expand Show data source
Used in treatment of hyperthyroidism expand Show data source
Empirical Formula (Hill Notation)
C4H6N2S expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich
MP Biomedicals - 02155390 external link
(2-Mercapto-1-methylimidazole; 1-Methylimidazole-2-thiol) Purity: 98% Crystalline
DrugBank - DB00763 external link
Item Information
Drug Groups approved
Description A thioureylene antithyroid agent that inhibits the formation of thyroid hormones by interfering with the incorporation of iodine into tyrosyl residues of thyroglobulin. This is done by interfering with the oxidation of iodide ion and iodotyrosyl groups through inhibition of the peroxidase enzyme. [PubChem]
Indication For the treatment of hyperthyroidism, goiter, Graves disease and psoriasis.
Pharmacology Used in the treatment of hyperthyroidism or an overactive thyroid gland, methimazole inhibits the synthesis of thyroid hormones and thus is effective in the treatment of hyperthyroidism. It may also be used to ameliorate hyperthyroidism in preparation for subtotal thyroidectomy or radioactive iodine therapy.
Toxicity Oral LD50 in rats is 2250 mg/kg. Symptoms of overdose include nausea, vomiting, epigastric distress, headache, fever, joint pain, pruritus, and edema. Aplastic anemia (pancy-topenia) or agranulocytosis may be manifested in hours to days. Less frequent events are hepatitis, nephrotic syndrome, exfoliative dermatitis, neuropathies, and CNS stimulation or depression.
Affected Organisms
Humans and other mammals
Biotransformation Primarily hepatic. Metabolized rapidly, requiring frequent administration.
Absorption Rapid with an oral bioavailability of 93%.
Half Life 5-6 hours
Protein Binding None or minimal
Elimination Methimazole is excreted in the urine.
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals - S1609 external link
Research Area: Endocrinology
Biological Activity:
Methimazole(Tapazole, Northyx) is an antithyroid medicine. Methimazole is used to treat hyperthyroidism, a condition where the thyroid gland produces too much thyroid hormone. It is also used before thyroid surgery or radioactive iodine treatment. [1] Methimazole inhibits the addition of iodine to thyroglobulin by the enzyme thyroperoxidase, a necessary step in the synthesis of triiodothyronine(T3) and thyroxine(T4). It does not inhibit the action of the sodium-dependent iodide transporter located on follicular cells’ basolateral membranes. Inhibition of this step requires competitive inhibitors such as perchlorate and thiocyanate. [1]
Sigma Aldrich - 301507 external link
Packaging
5, 25 g in glass bottle
Sigma Aldrich - 46429 external link
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC
Sigma Aldrich - M8506 external link
Application
Used to model hypothyroidism in experimental animals.
Biochem/physiol Actions
甲巯咪唑为硫脲抗甲状腺剂,可阻止碘有机化,从而抑制甲状腺素的合成。
包装
25, 100 g in glass bottle

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • •  http://en.wikipedia.org/wiki/Methimazole
  • • Aldrich Library of 13C and 1H FT NMR Spectra, 1992, 3, 81A, (nmr)
  • • Aldrich Library of FT-IR Spectra, 1st edn., 1985, 2, 617A, (ir)
  • • Wohl, A. et al., Ber., 1889, 22, 1353, (synth)
  • • Jones, R.G. et al., J.A.C.S., 1949, 71, 4000, (synth)
  • • Bowie, J.H. et al., Aust. J. Chem., 1967, 20, 1613, (ms)
  • • Langer, P., Endocrinology (Baltimore), 1968, 83, 1268, (pharmacol)
  • • Faure, R. et al., Org. Magn. Reson., 1977, 9, 688, (cmr)
  • • Mille, G. et al., C. R. Hebd. Seances Acad. Sci. Ser. C, 1978, 286, 477, (ir)
  • • Aboul-Enein, H.Y. et al., Anal. Profiles Drug Subst., 1979, 8, 351, (rev)
  • • Kister, J. et al., Can. J. Chem., 1979, 57, 813, (derivs, synth)
  • • Bouin-Roubaud, D. et al., Can. J. Chem., 1981, 59, 2883, (uv)
  • • Skellern, G.G. et al., Xenobiotica, 1981, 11, 627, (metab)
  • • Raper, E.S. et al., Acta Cryst. B, 1983, 39, 355, (cryst struct)
  • • Anjaneyulu, B. et al., J. Labelled Compd. Radiopharm., 1983, 20, 951, (synth)
  • • Merck Index, 10th edn., 1983, No. 5844
  • • Cooper, D.S. et al., Endocrinology (Baltimore), 1984, 114, 786, (pharmacol)
  • • Stefaniak, L. et al., Magn. Reson. Chem., 1986, 23, 166, (tautom)
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 180, (synonyms)
  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 534
  • • Guziec, L.J. et al., J.O.C., 1994, 59, 4691, (synth, cmr)
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, MCO500
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PATENTS

PATENTS

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