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	467-43-6 730-68-7 (no salt)
PubChem CID	3032307
ChemSpider	2297317
UNII	DZQ457UJ3Y
ChEMBL	ChEMBL2104624
CompTox Dashboard (EPA)	DTXSID10861962
Chemical and physical data
Formula	C12H20N2O2S2
Molar mass	288.42 g·mol−1
3D model (JSmol)	Interactive image
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

• Barbiturate