Emylcamate

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.

Emylcamate

Clinical data
ATC code	N05BC03 (WHO)
Legal status
Legal status	BR: Class C1 (Other controlled substances)[1]
Identifiers
IUPAC name 3-methyl-3-pentanol carbamate
CAS Number	78-28-4 Y
PubChem CID	6526
DrugBank	DB13572 Y
ChemSpider	6278 Y
UNII	KCJ747D3R4
KEGG	D07317 Y
ChEBI	CHEBI:134769
ChEMBL	ChEMBL2104208 Y
CompTox Dashboard (EPA)	DTXSID40228645
ECHA InfoCard	100.001.002
Chemical and physical data
Formula	C7H15NO2
Molar mass	145.202 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(OC(C)(CC)CC)N
InChI InChI=1S/C7H15NO2/c1-4-7(3,5-2)10-6(8)9/h4-5H2,1-3H3,(H2,8,9) Y Key:SLWGJZPKHAXZQL-UHFFFAOYSA-N Y

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

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

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

• Shorter E (August 2004). "Olhando para trás: um novo caminho possível para a descoberta de drogas em psicofarmacologia" [Looking back: a new possible path for drug discovery in psychopharmacology.]. Revista de Psiquiatria do Rio Grande do Sul (in Portuguese). 26 (2): 196–203. doi:10.1590/S0101-81082004000200009.

External links

• "Emylcamate". The Comparative Toxicogenomics Database.
• "Emylcamate". BIAM (in French). Archived from the original on 2022-09-26. Retrieved 2005-12-22.