:Methitural
{{short description|Chemical compound}}
{{Drugbox
| IUPAC_name = 5-[2-(methylsulfanyl)ethyl]-5-(2-pentanyl)-2-thioxodihydro-4,6(1H,5H)-pyrimidinedione
| image = Methitural.svg
| CAS_number = 467-43-6
| CAS_supplemental =
730-68-7 (no salt)
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = DZQ457UJ3Y
| ATC_prefix = None
| ATC_suffix =
| PubChem = 3032307
| ChEMBL = 2104624
| ChemSpiderID = 2297317
| C = 12 | H = 20 | N = 2 | O = 2 | S = 2
| smiles = O=C1NC(=S)NC(=O)C1(C(C)CCC)CCSC
| StdInChI = 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)
| StdInChIKey = KEMCRVSPPRNENL-UHFFFAOYSA-N
| bioavailability =
| protein_bound =
| metabolism =
| elimination_half-life =
| excretion =
| pregnancy_category =
| legal_status =
| routes_of_administration =
}}
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.{{cite book | vauthors = Macdonald F | title = Dictionary of Pharmacological Agents | url = https://books.google.com/books?id=A0THacd46ZsC&pg=PA1300 | access-date = 19 May 2012 | year = 1997 | publisher = CRC Press | isbn = 978-0-412-46630-4 | page = 1300}}{{cite journal | vauthors = Houde J, Hudon F, Jacques A | title = Neraval (methitural sodium) (sch. 3132) | journal = Canadian Anaesthetists' Society Journal | volume = 4 | issue = 1 | pages = 43–6 | date = January 1957 | pmid = 13396640 | doi = 10.1007/bf03009193 | doi-access = free }}{{cite journal | vauthors = Irwin S, Stagg RD, Dunbar E, Govier WM | title = Methitural, a new intravenous anesthetic: comparison with thiopental in the cat, dog and monkey | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 116 | issue = 3 | pages = 317–25 | date = March 1956 | pmid = 13307393 | url = http://jpet.aspetjournals.org/cgi/pmidlookup?view=long&pmid=13307393 }}
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
References
{{Reflist}}
{{Anesthetics}}
{{GABAAR PAMs}}
Category:GABAA receptor positive allosteric modulators
{{sedative-stub}}