Chemistry:Methitural

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Short description: Chemical compound
Methitural
Clinical data
ATC code
  • None
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC12H20N2O2S2
Molar mass288.42 g·mol−1
3D model (JSmol)

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

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

References

  1. ↑ Dictionary of Pharmacological Agents. CRC Press. 1997. p. 1300. ISBN 978-0-412-46630-4. https://books.google.com/books?id=A0THacd46ZsC&pg=PA1300. Retrieved 19 May 2012. 
  2. ↑ "Neraval (methitural sodium) (sch. 3132)". Canadian Anaesthetists' Society Journal 4 (1): 43–6. January 1957. doi:10.1007/bf03009193. PMID 13396640. 
  3. ↑ "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. March 1956. PMID 13307393. http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=13307393.