1-methyl-2,3-dihydro-1H-imidazole-2-thione

• ChemBase ID: 643
• Molecular Formular: C4H6N2S
• Molecular Mass: 114.16884
• Monoisotopic Mass: 114.0251692
• 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 60-56-0
• EC Number: 200-482-4
• MDL Number: MFCD00179321
• Beilstein Number: 108646
• PubChem SID: 24870159; 24858194; 24882870; 46506536; 160964106; 24897266
• 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

JChem

• Acid pKa: 10.411967
• H Acceptors: 0
• H Donor: 1
• LogD (pH = 5.5): 0.74566555
• LogD (pH = 7.4): 0.74527997
• Log P: 0.7456705
• Molar Refractivity: 33.2322 cm^3
• Polarizability: 12.8416 Å^3
• Polar Surface Area: 15.27 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.38
• LOG S: -1.0
• Solubility (Water): 1.13e+01 g/l

PROPERTIES

Physical Property

• Solubility: 2.75 mg/mL (20°C); 275 g/L
• Melting Point: 143-145 °C; 144-147 °C(lit.); 144-147°C; 146°C (294.8°F); 146-148
• Boiling Point: 280(dec.)°C
• Flash Point: >100°C
• Hydrophobicity(logP): -0.2

Safety Information

• Storage Condition: -20°C; Room Temperature (15-30°C)
• Storage Warning: Harmful/Irritant/Teratogenic/Stench/Store under Argon
• RTECS: NI8615000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 63-43-62; R:22
• Safety Statements: 26-27-36-45; S:36/37/39
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H317-H361
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves; 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

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: 93%
• Excretion: Renal
• Half Life: 5-6 hours
• Metabolism: Hepatic
• Protein Bound: None
• Legal Status: Rx-only (US)
• Pregnancy Category: D (US)
• Gene Information: human ... CYP1A2(1544)
• Mechanism of Action: Thyroid hormone synthesis inhibitor

Product Information

• Purity: ≥97.0% (S); ≥99%; 95+%; 98%
• Grade: analytical standard; purum; VETRANAL™, analytical standard
• Salt Data: Free Base
• Application(s): Antithyroid; Used in treatment of hyperthyroidism
• Empirical Formula (Hill Notation): C4H6N2S

DETAILS

MP Biomedicals - 02155390

(2-Mercapto-1-methylimidazole; 1-Methylimidazole-2-thiol) Purity: 98% Crystalline

DrugBank - DB00763

• 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

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

Packaging
5, 25 g in glass bottle

Sigma Aldrich - 46429

Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC

Sigma Aldrich - M8506

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

• 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