Methitural
Chemical compound
- None
- 5-[2-(methylsulfanyl)ethyl]-5-(2-pentanyl)-2-thioxodihydro-4,6(1H,5H)-pyrimidinedione
- 467-43-6
730-68-7 (no salt)
- 3032307
- 2297317
- DZQ457UJ3Y
- ChEMBL2104624
- Interactive image
- 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
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
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
References
- ^ Macdonald F (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1300. ISBN 978-0-412-46630-4. Retrieved 19 May 2012.
- ^ 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.
- ^ 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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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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