Tybamate: Difference between revisions

{{Short description|Chemical compound}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

| IUPAC_name = [2-(Carbamoyloxymethyl)-2-methylpentyl] ''N''-butylcarbamate

| image = Tybamate.svg

|width=201

| CAS_number_Ref = {{cascite|correct|CAS}}

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 19092

| smiles = CCCCNC(=O)OCC(C)(CCC)COC(=O)N

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C13H26N2O4/c1-4-6-8-15-12(17)19-10-13(3,7-5-2)9-18-11(14)16/h4-10H2,1-3H3,(H2,14,16)(H,15,17)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = PRBORDFJHHAISJ-UHFFFAOYSA-N

'''Tybamate''' ([[International Nonproprietary Name|INN]]; '''Solacen''', '''Tybatran''', '''Effisax''') is an [[anxiolytic]] of the [[carbamate]] family.<ref name="TaylorFrancis2000">{{cite book | title = Index Nominum 2000: International Drug Directory | url = https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA634 | date = January 2000 | publisher = Taylor & Francis | isbn = 978-3-88763-075-1 | page = 1077}}</ref> It is a [[prodrug]] for [[meprobamate]] in the same way as the better known drug [[carisoprodol]]. It has liver enzyme inducing effects similar to those of [[phenobarbital]] but much weaker.<ref name="pmid4023427">{{cite journal | vauthors = Segelman FH, Kelton E, Terzi RM, Kucharczyk N, Sofia RD | title = The comparative potency of phenobarbital and five 1,3-propanediol dicarbamates for hepatic cytochrome P450 induction in rats | journal = Research Communications in Chemical Pathology and Pharmacology | volume = 48 | issue = 3 | pages = 467–70 | date = June 1985 | pmid = 4023427 }}</ref>

As the trade name Tybatran ([[Wyeth|Robins]]), it was formerly available in capsules of 125, 250, and 350 mg, taken 3 or 4 times a day for a total daily dosage of 750 mg to 2 g. The plasma half-life of the drug is three hours. At high doses in combination with [[phenothiazine]]s, it could produce convulsions.<ref>{{cite book |page=406 |title=AMA Drug Evaluations |edition=3rd |date=1977 |publisher=Pub. Sciences Group |location=Littleton, Mass. |author=American Medical Association Dept of Drugs |isbn=978-0-88416-175-2 |oclc=1024170745}}</ref>

==Synthesis==

:[[File:Tybamate synthesis.svg|upright=2]]

[[Catalytic hydrogenation]] of 2-methyl-2-pentenal (1) gives the [[aldehyde]] 2-methylpentanal (2). Treatment with [[formaldehyde]] gives a [[crossed Cannizzaro reaction]] yielding [[2-Methyl-2-propyl-1,3-propanediol|2,2-''bis''(hydroxymethyl)pentane]] (3). [[Cyclisation]] of this [[diol]] with [[diethyl carbonate]] gives (4), which reacts with ammonia to provide the [[carbamate]] (5). Lastly, treatment with butyl isocyanate (6) produces tybamate.<ref>{{cite journal |doi=10.1021/ja01156a086 |title=Some Anticonvulsant Agents Derived from 1,3-Propanediols |date=1951 | vauthors = Ludwig BJ, Piech EC |journal=Journal of the American Chemical Society |volume=73 |issue=12 |pages=5779–5781 }}</ref><ref>{{cite book |doi=10.1016/S0099-5428(08)60025-8 |title=Tybamate |series=Analytical Profiles of Drug Substances |date=1975 | vauthors = Reisberg P, Kress J, Bodin JI |volume=4 |pages=494–515 |isbn=978-0-12-260804-9 }}</ref><ref>{{cite web |url=

https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-20-0207 |title=Tybamate | work = Pharmaceutical Substances |publisher=Thieme |access-date=2024-07-08}}</ref>

==References==

{{Reflist}}

{{GABAAR PAMs}}

[[Category:Anxiolytics]]

[[Category:GABAA receptor positive allosteric modulators]]

{{Anxiolytic-stub}}