Scopolamine butyl bromid

Frascht M, Schneider S, Schuman M, Wennig R (2007) Formation of scopolamine from /V-butyl-scopolamine bromide in cigarettes. J Anal Toxicol 31 220-223... 

Butylscopolamine bromide Scopolamine butyl bromide Hyoscin butyl bromide)... 

Common Name Butylscopolamin(e) bromide Butylscopolamini bromidum Butylscopolammonium bromide Hyoscine butyl bromide Scopolamine butyl bromide Scopolaminium butylbromatum... 

Synonyms. Butylscopolamonii Bromidum Hyoscine-A-Butyl Bromide Scopolamine Butylbromide. 

Hyoscine-N-butyl bromide is a quaternary ammonium variant of hyoscine (scopolamine) formed by adding a butyl group to the tertiary amine group. It is mainly used to relieve temporal spasms of the intestine or menstrual cramps. It produces very moderate side effects, especially in the CNS. The long-term use of hyoscine-N-butyl bromide for the treatment of irritable bowel syndrome (IBS) has been reported as well (three daily doses of 10 mg). The dmg is available in oral dosage forms with doses of 10-35 mg. 

Over the past few decades, the biosyntheses of tropane alkaloids such as (—)-hyoscyamine, (—)-scopolamine, and (—)-cocaine have been studied extensively [18]. The skeletons of all these alkaloids feature the tropinone moiety, produced by oxidation and subsequent cyclization of (-b)-hygrine (17) [19]. It was envisioned that RCM could be invoked in order to develop an enantioselective synthesis of 17 [20]. As depicted in Scheme 2.5, a phase-transfer catalytic allylation reaction with methaUyl bromide converted t-butyl ester 13 into product 14 with 97% ee. Metathesis precursor 15 was then prepared in six more steps, including transformation of the t-butyl ester of 14 into a terminal olefin. Dihydropyrrole 17 was formed in quantitative yield by RCM employing [Ru]-II (8 mol%). Subsequent hydrogenation and deprotection of 16 led to (-l-)-hygrine 17 with overall yield of 29% and an ee of 97%. 

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