Methitural

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]

Methitural
Clinical data
ATC code
  • None
Identifiers
IUPAC name
  • 5-[2-(methylsulfanyl)ethyl]-5-(2-pentanyl)-2-thioxodihydro-4,6(1H,5H)-pyrimidinedione
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC12H20N2O2S2
Molar mass288.42 g·mol−1
3D model (JSmol)
SMILES
  • O=C1NC(=S)NC(=O)C1(C(C)CCC)CCSC
InChI
  • InChI=1S/C12H20N2O2S2/c1-4-5-8(2)12(6-7-18-3)9(15)13-11(17)14-10(12)16/h8H,4-7H2,1-3H3,(H2,13,14,15,16,17)
  • Key:KEMCRVSPPRNENL-UHFFFAOYSA-N

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. Macdonald F (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.
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