Strychnine N-oxide

Tab. 14.3 Chemical shift assignments for strychnine (1), brucine (51), holstiine (52), strychnine N-oxide (54), and brucine N-oxide (55) in deuterochloroform.

Strychnine is rapidly metabolized by the liver microsomal enzyme system requiring NADPH and O2. Five metabolites formed in vitro by rabbit fiver were isolated and identified as 2 -hydroxystrycfinine, 11,12-defiydrostrychnine, strychnine-21, 22-epoxide, 21,22-dihydroxy-22-hydrostrychnine, and strychnine-N-oxide which was the major metabolite and accounted for approximately 15% of the metabolized strychnine. AU other metabolites accounted for less than 1% (Mishimaetfl/., 1985). Similar metabolites were identified in rat urine where the major metabolite was strychnine-21,22-epoxide (Oguri et a/., 1989). The metabolic fate of strychnine in humans is unknown. 

Strychnine-N-oxide, strychnic acid Methylergometrine Dihydroergotamine N-Butylscopolamine bromide... 

Such a path would obviate the necessity of putting a double bond at a bridgehead in the related case of the oxidation of strychnine N-oxide to... 

Strychnine N-oxide Absorbs (strongly) lodoplatinate Dragendorff... 

Strychnine is rapidly metabolized by the liver microsomal enzyme system and requires NADPH and O2. Five metabolites formed in vitro by rabbit liver were isolated and identified as 2-hydroxystrychnine, 11,12-dehydro-strychnine, strychnine-21,22-epoxide, 21,22-dihydroxy-22-hydrostrychnine, and strychnine-N-oxide, which was... 

Using gas chromatography of the N-oxide of the pseudo series of the alkaloids, decomposition of the alkaloids was observed in all cases, giving strychnine as the main peak on the chromatograms. The authors presumed that this decomposition might be due to the use of a... 

Strychnine-Akuammicine-Ellipticine Group.—Very few new extractions have been recorded during the year under review. (- )-Akuammicine occurs in the leaves of Hunteria elliottii and in the aerial parts of V. major. A cytotoxic constituent of the roots of Tabernaemontana holstii K. Schum. proves to be tubotaiwine N-oxide. Olivacine and apparicine have been found in the leaves of Pagiantha cerifera. ... 

Both neostrychnine and N-methyl-5-methoxy-4,5-dihydroneo-strychnine were oxidized by potassium permanganate with insertion of two oxygen atoms. One oxygen was clearly a keto function and the other apparently a carbonyl in a lactam rather than an... 

Mole-nots, see Strychnine Mollan 0, see Bis(2-ethylhexyl) phthalate Mondur TD, see 2,4-Toluene diisocyanate Mondur TD-80, see 2,4-Toluene diisocyanate Mondur TDS, see 2,4-Toluene diisocyanate Monobromobenzene, see Bromobenzene Monobromobenzol, see Bromobenzene Monobromoethane, see Ethyl bromide Monobromomethane, see Methyl bromide Monobromotrifluoromethane, see Bromotrifluoromethane Monobutylamine, see Butylamine Mono-n-butylamine, see Butylamine Monobutyl ethylene glycol ether, see 2-Butoxyethanol Monochlorbenzene, see Chlorobenzene Monochlorethane, see Chloroethane Monochloroacetaldehyde, see Chloroacetaldehyde Monochlorobenzene, see Chlorobenzene Monochlorodibromomethane, see Dibromochloromethane Monochlorodiphenyl oxide, see 4-Chlorophenyl phenyl ether... 

In practically all the instances of its use, attack of a double bond and of C-20 (between Nb and the C-21 to C-22 double bond) occurs. There is no instance of the simple oxidative disruption of a benzene nucleus indeed, the most vigorous conditions, aqueous alkaline permanganate at 50°-70°, lead to the oxidation of strychnine to N-oxalylanthranilic acid in about 8% yield. Brucine likewise gives 4,5-dimethoxy-iV-oxalyl-anthranilic acid, but in much lower yield (0.1 to 0.2%) (18). a-Colubrine (3-methoxystrychnine) gave a 2.7% yield of 4-methoxy- and /J-colubrine (2-methoxystrychnine) a 5.5% yield of 5-methoxy-iV-oxalylanthranilic acid (125). These oxidations fixed the positions of the methoxyl groups in the last three alkaloids. 

Although the correct structural formula had been intuitively proposed earlier, the structure of strychnine was founded on a firm basis only when Woodward 6t al.8 discovered that strychnone obtained from the oxidation of IP-strychnine gave ultra-violet absorption maxima resembling those of N-acylindoles. Strychnine, oh the other hand, gives bands similar to N-acyldihydroindoles. Woodward and McLamore recently established the structure of another alkaloid, semperivinine, on the basis of its ultra-violet absorption spectrum. (For absorption data of alkaloids. see references 94 and 95.)... 

Phillipson, J. D. and Bisset, N. G. (1972) Quatemisation and oxidation of strychnine and brucine during plant extraction. Phytochemistry 11,2547—2553. 

N. A. Freobrashenski (69). On resolution through the strychnine salt, the d- and i-forms were obtained, the former being identical with d-iso-pilopic acid obtained by the oxidation of isopilocarpine and purified through the strychnine salt. The solid ester (XXXIII) similarly gave dZ-pilopic acid, which is readily isomerized to dZ-isopilopic acid when heated (61). It was resolved through the brucine and cinchonine salts (62). 

H30N2O9S, Strychnine sulphonic acid tetrahydrate, 39B, 423 H31CIN2O5, 2-Phenylsparteine N(16)-oxide monoperchlorate, 43B,... 

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