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{{Short description|Chemical compound}}
{{Short description|Chemical compound}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{Drugbox
{{Drugbox
| IUPAC_name = [2-(Carbamoyloxymethyl)-2-methylpentyl] ''N''-butylcarbamate
| IUPAC_name = [2-(Carbamoyloxymethyl)-2-methylpentyl] ''N''-butylcarbamate
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==Synthesis==
==Synthesis==
:[[File:Tybamate synthesis.svg|upright=2]]
:[[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 |last1=Ludwig |first1=B. J. |last2=Piech |first2=E. C. |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 |last1=Reisberg |first1=Philip |last2=Kress |first2=John |last3=Bodin |first3=Jerome I. |volume=4 |pages=494–515 |isbn=978-0-12-260804-9 }}</ref><ref>{{cite web |url=
[[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 |=Ludwig Piech |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 |=Reisberg Kress Bodin |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 |publisher=Thieme |access-date=2024-07-08}}</ref>
https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-20-0207 |title=Tybamate |publisher=Thieme |access-date=2024-07-08}}</ref>


==References==
==References==

Revision as of 08:21, 9 July 2024

Tybamate
Clinical data
ATC code
  • none
Identifiers
  • [2-(Carbamoyloxymethyl)-2-methylpentyl] N-butylcarbamate
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.022.050 Edit this at Wikidata
Chemical and physical data
FormulaC13H26N2O4
Molar mass274.361 g·mol−1
3D model (JSmol)
  • CCCCNC(=O)OCC(C)(CCC)COC(=O)N
  • InChI=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) checkY
  • Key:PRBORDFJHHAISJ-UHFFFAOYSA-N checkY

Tybamate (INN; Solacen, Tybatran, Effisax) is an anxiolytic of the carbamate family.[1] 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.[2]

As the trade name Tybatran (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 phenothiazines, it could produce convulsions.[3]

Synthesis

Catalytic hydrogenation of 2-methyl-2-pentenal (1) gives the aldehyde 2-methylpentanal (2). Treatment with formaldehyde gives a crossed Cannizzaro reaction yielding 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.[4][5][6]

References

  1. ^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. p. 1077. ISBN 978-3-88763-075-1.
  2. ^ Segelman FH, Kelton E, Terzi RM, Kucharczyk N, Sofia RD (June 1985). "The comparative potency of phenobarbital and five 1,3-propanediol dicarbamates for hepatic cytochrome P450 induction in rats". Research Communications in Chemical Pathology and Pharmacology. 48 (3): 467–70. PMID 4023427.
  3. ^ American Medical Association Dept of Drugs (1977). AMA Drug Evaluations (3rd ed.). Littleton, Mass.: Pub. Sciences Group. p. 406. ISBN 978-0-88416-175-2. OCLC 1024170745.
  4. ^ Ludwig BJ, Piech EC (1951). "Some Anticonvulsant Agents Derived from 1,3-Propanediols". Journal of the American Chemical Society. 73 (12): 5779–5781. doi:10.1021/ja01156a086.
  5. ^ Reisberg P, Kress J, Bodin JI (1975). Tybamate. Analytical Profiles of Drug Substances. Vol. 4. pp. 494–515. doi:10.1016/S0099-5428(08)60025-8. ISBN 978-0-12-260804-9.
  6. ^ "Tybamate". Pharmaceutical Substances. Thieme. Retrieved 2024-07-08.



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