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Methitural

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
Methitural
Clinical data
ATC code
  • None
Identifiers
  • 5-[2-(methylsulfanyl)ethyl]-5-(2-pentanyl)-2-thioxodihydro-4,6(1H,5H)-pyrimidinedione
CAS Number
PubChemCID
ChemSpider
UNII
ChEMBL
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC12H20N2O2S2
Molar mass288.42 g·mol−1
3D model (JSmol)
  • O=C1NC(=S)NC(=O)C1(C(C)CCC)CCSC
  • 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

Methitural (INN;Neraval,Thiogenal), ormethitural sodium, also known asmethioturiate, is abarbituratederivative which was marketed in the 1950s inEurope (inGermany andItaly) as an ultra-short-actingintravenousanesthetic.[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 substitutedcyanoacetate (1) with 2-chloroethylmethyl sulfide (2). Condensation of the resulting cyanoester (3) withthiourea followed by hydrolysis of the resulting imine affords methitural.

See also

[edit]

References

[edit]
  1. ^Macdonald F (1997).Dictionary of Pharmacological Agents. CRC Press. p. 1300.ISBN 978-0-412-46630-4. Retrieved19 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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