Methitural

In today's world, Methitural is a relevant topic that impacts people of all ages, genders, and backgrounds. The importance of addressing this issue lies in its influence on different aspects of daily life, from physical and emotional health to social and economic development. Throughout history, Methitural has been the subject of extensive research and debate, giving rise to a wide range of perspectives and approaches on how to approach it. In this article, we will explore different aspects of Methitural, from its origins to its implications today, in order to provide a comprehensive and up-to-date view on this topic.

Methitural
Clinical data
ATC code
  • None
Identifiers
  • 5--5-(2-pentanyl)-2-thioxodihydro-4,6(1H,5H)-pyrimidinedione
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
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), 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.

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

  1. ^ Macdonald F (1997). Dictionary of Pharmacological Agents. CRC Press. p. 1300. ISBN 978-0-412-46630-4. Retrieved 19 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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