Naratriptan hydrochloride

USAN Naratriptan hydrochloride Trade Name Amerge Company. GlaxoSmithKline Launched 1998 M.W 335.47... 

The synthesis of a C-labelled version of naratriptan (3b) is highlighted in Scheme The indole ring of naratriptan hydrochloride (3) was oxidatively cleaved using sodium periodate to give ketoformanilide 45. Cyanation of 45 with potassium [ C]cyanide in aqueous ethanol gave the intermediate amidine 46, which was reduced directly with NaBH4 in acetic acid to afford C-labelled naratriptan (3b), which was isolated as the hydrochloride salt. 

Nammig (Naratriptan hydrochloride). GlaxoSmithKline UK. UK Summary of product characteristics, November 2005. 

Amerge (Naratriptan hydrochloride). G oSmitiiKUne. US Prescribing information, April... 

Triptans have provided a futile ground for indole synthesis employing both the Heck and the intramolecular Heck reaction. In Glaxo s process synthesis of naratriptan, the reaction of 5-bromoindole with A -methyl-4-piperidone gave the A -methyl-tetrahydropyridinyl substituted indole. The Heck reaction between the 5-bromoindole and the A -methylvinylsulfonamide was carried out on 700-g scales. Both double bonds of the resulting diene were hydrogenated to give naratriptan hydrochloride as white crystals in 71% yield after recrystallization from hot water. 

Naratriptan hydrochloride tablets (2.5 mg). Adult dose 1.0-2.5 mg. Maximum of 5 mg within 24 hours. 

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