Methitural
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| 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 |
| Molar mass | 288.429 g/mol |
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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
- ↑ F.. Macdonald (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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