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Emylcamate

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Emylcamate
Clinical data
ATC code
Legal status
Legal status
Identifiers
  • 3-methyl-3-pentanol carbamate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.001.002 Edit this at Wikidata
Chemical and physical data
FormulaC7H15NO2
Molar mass145.202 g·mol−1
3D model (JSmol)
  • O=C(OC(C)(CC)CC)N
  • InChI=1S/C7H15NO2/c1-4-7(3,5-2)10-6(8)9/h4-5H2,1-3H3,(H2,8,9) checkY
  • Key:SLWGJZPKHAXZQL-UHFFFAOYSA-N checkY

Emylcamate (marketed as Striatran by Merck) is an anxiolytic and muscle relaxant. It was patented in the US in 1961 (US Patent 2,972,564) and advertised for the treatment of anxiety and tension. It was claimed to be superior to meprobamate, which would eventually replace emylcamate.

A study of the drug's effects in mice was done in 1959. It concluded that at 50 mg/kg emylcamate gave a 63% decrease in motor activity compared with meprobamate's 32% decrease, a doubling in effective potency. The therapeutic index in mice was also established:

Meprobamate Emylcamate Effect
175 123 ED50 (mg/kg)
600 550 LD50 (mg/kg)
3.4 4.4 Therapeutic index

Emylcamate also has a faster intra-parenteral onset than meprobamate, 3 minutes compared with 35.[2]

Synthesis

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Emylcamate is the carbamate of the tertiary alcohol 3-methyl-3-pentanol. The first patented synthesis involved treating that alcohol with potassium cyanate and trichloroacetic acid.[3] In 1963, an improved synthesis was reported using sodium cyanate and trifluoroacetic acid.[4]

References

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  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ Melander B (1959). "Emylcamate, A Potent Tranquillizing Relaxant". Journal of Medicinal and Pharmaceutical Chemistry. 1 (5): 443–457. doi:10.1021/jm50006a003.
  3. ^ US patent 2972564, Melander BO, Hanshoff G, "3-Methyl-3-pentanol carbamate compositions having muscle relaxing and tranquilizing action", issued 1961-02-21, assigned to Phadia AB 
  4. ^ Loev B, Kormendy MF (1963). "An Improved Synthesis of Carbamates". The Journal of Organic Chemistry. 28 (12): 3421–3426. doi:10.1021/jo01047a033.

Further reading

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