Methitural

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Methitural
Methitural.svg
Systematic (IUPAC) name
5-[2-(methylsulfanyl)ethyl]-5-(2-pentanyl)-2-thioxodihydro-4,6(1H,5H)-pyrimidinedione
Identifiers
CAS Number 467-43-6
730-68-7 (no salt)
ATC code None
PubChem CID 3032307
ChemSpider 2297317
ChEMBL CHEMBL2104624
Chemical data
Formula C12H20N2O2S2
Molar mass 288.429 g/mol

Methitural (INN; Neraval, Thiogenal), or methitural sodium, also known as methioturiate, is a barbiturate derivative which was marketed in the 1950s in Europe (in Germany and Italy) as an ultra-short-acting intravenous anesthetic.[1][2][3]

Synthesis[edit]

Methitural synthesis: Zima, Von Werder, U.S. Patent 2,802,827 (1957 to E. Merck).

A somewhat more complex side chain is incorporated by alkylation of the carbanion of the substituted cyanoacetate (1) with 2-chloroethylmethyl sulfide (2). Condensation of the resulting cyanoester (3) with thiourea followed by hydrolysis of the resulting imine affords methitural.

See also[edit]

References[edit]

  1. ^ F.. Macdonald (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1300. ISBN 978-0-412-46630-4. Retrieved 19 May 2012. 
  2. ^ HOUDE J, HUDON F, JACQUES A (January 1957). "Neraval (methitural sodium) (sch. 3132)". Canadian Anaesthetists' Society Journal. 4 (1): 43–6. doi:10.1007/bf03009193. PMID 13396640. 
  3. ^ IRWIN S, STAGG RD, DUNBAR E, GOVIER WM (March 1956). "Methitural, a new intravenous anesthetic: comparison with thiopental in the cat, dog and monkey". The Journal of Pharmacology and Experimental Therapeutics. 116 (3): 317–25. PMID 13307393.