Methylthiouracil

Chemical properties

white powder

The Uses of Methylthiouracil

antithyroid agent

The Uses of Methylthiouracil

6-?Methyl-?2-?thiouracil is a derivative of methylthiouracil (M330710), a competitive inhibitor of Nitric Oxide Synthase (NOS). Potential anti-inflammatory agent.

Definition

ChEBI: Methylthiouracil is a pyrimidone.

General Description

White crystalline powder with an odor of onions and a bitter taste. A saturated aqueous solution is neutral or slightly acidic.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

Methylthiouracil reacts with strong oxidizing agents. Forms complexes with metals and is oxidized by iodine and other sulfhydryl oxidizing agents .

Fire Hazard

Flash point data for Methylthiouracil are not available. Methylthiouracil is probably combustible.

Safety Profile

Confirmed carcinogen with experimental carcinogenic, neoplastigenic, tumorigenic, and teratogenic data. Poison by intraperitoneal route. Moderately toxic by ingestion. Human teratogenic and reproductive effects by an unspecified route: developmental abnormalities of the endocrine system and effects on newborn including neonatal measures or effects. Experimental reproductive effects. Used to treat hyperthyroidism. When heated to decomposition it emits very toxic fumes of NOx and SOx.

Purification Methods

Crystallise the thiouracil from a large volume of H2O. Purify it further by dissolving in base, adding charcoal, filtering and acidifying with AcOH. Suspend the wet solid (ca 100g) in boiling H2O (1L), stir and add AcOH (20mL), stir and refrigerate. Collect the product, wash it with cold H2O (4 x 200mL), drain it for several hours then place it in an oven at 70o to constant weight. [IR: Short & Thompson J Chem Soc 168 1952, Foster & Snyder Org Synth Coll Vol IV 638 1063, Beilstein 24 III/IV 1289.]