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
Molecular mass 288.429 g/mol
  • 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), 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

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