Alkaloids brucine

A solution of the alkaloid brucine in concentrated sulfuric acid was reported [4, 38, 50] to give orange-red colors with nitrate esters and nitramines, probably by oxidation ofbmcine. 

Strychnos nux-vomica L. Fan Mu Pen (Strychnine) (seed) Strychnine, monomeric tertiary indole alkaloids, brucine.50 144-504 This herb is highly toxic. Treat neurasthenia, aphrodisiac, vasomotor stimulation, regulate blood pressure, treat nerve diseases. 

One of the more salient points concerning an unBymmetrically substituted oxaoirane ring is that it has an asymmetric carbon atom and should be capable of resolution into optically active form. TV oxazirane (XIX) has in fact been partially resolved (o -S.d4 ) by treating it with the alkaloid brucine under the correct conditions i... 

Distinction should be made at this time between diastereoisomers and enantiomers. The former are characterized by the presence of at least two closely associated asymmetric centers in the molecular structure, either of which can epimerize. Altogether then there are two pairs of enantiomers for a total of four stereochemically unique individuals. Diastereoisomers have different physical properties and as a result discriminations, and even separations, can be done relatively easily. Enantiomers on the other hand differ in only one physical property, i.e. the direction of rotation of polarized light. Reaction of an enantiomeric racemic mixture with a third chiral species will produce a mixture of diastereomers therefore facilitating their identification or their separation. Early examples of this were the separations done by fractional crystallization of salts produced by a derivatization reaction with, for example, the alkaloid (-)-brucine. Fractional crystallization would never seem to be an effective analytical method yet it was used with some success in a forensic sciences context to confirm the presence of (L)-cocaine by a carefully contrived microcrystalline test. The physical properties... 

S,Cinchona alkaloids,brucine,strychnine, emetine.reser-pine. yohimbine, caffeine Detection with conductance detector Silica gel 10 pm CHC13-MeOH-hexane(7 3 10) 36... 

Acids and lactones Alkaloids (brucine, strychnine, quinidine, quinine, chinchonine, chinchonidine, dehydroabietylamine, quinotoxine, cinchotoxine), terpene derivatives (endo-bomylamine, 1 R-3-endo-aminobomeol, pinelylamines, (+)-3-aminomethylpinane) ephedrine and ephedrine analogs, synthetic amines (d-methyl-benzylamine and its derivatives, d-l-naphthylethyl-amine, 2-amino-l,2-diphenylethanol), amino acids and bases derived thereof [15-19] [20-23] [24,25-27] [28-31]... 

Toda has used alkaloids [brucine (22), sparteine (25)] to enantioselectively enclathrate chiral propargylic alcohols (Fig. 10). Hydrogen bonding is an essential part of the lattice build-up. In view of the large pool of natural alkaloids, the potential of the method is obvious. 

Synonyms Brucine alkaloid Brucine, solid 2,3-Dimethoxystrychnidin-10-one Dimethoxystrychnine 2,3-Dimethoxystrychnine... 

Brucine alkaloid Brucine, solid. See Brucine Brucine sulfate heptahydrate CAS 5787-00-8 EINECS/ELINCS 225-432-9 UN 1544 UN 1570 UN 2811 Synonyms Brucine sulfate (2 1) heptahydrate 10,11-Dimethoxystrychnine sulfate, heptahydrate Empirical C46H68N4O19S Formula (C23H26N204)2 H2SO4 6H2O Properties Off-wh. cryst. powd. m.w. 1013.13 m.p. 180 C (dec.)... 

Classification Specially denatured alcohol Definition Ethyl alcohol (100 gal) denatured with t-butyl alcohol (1/8 gal) and 1.5 oz of either brucine alkaloid, brucine sulfate NF, quassin, or combination thereof... 

However, the distribution of the individual compounds is restricted. This was first pointed out by Sachs (1882) and Pfeffer (1897), who demonstrated the lack of phylogenetic continuity of secondary substances such as oxalate, resins, and essential oils in the plant kingdom. Usually the more chemical reactions necessary for the synthesis of a given secondary product, the more restricted is its distribution. The alkaloid, nicotine, which is formed by a relatively simple biosynthetic pathway (D 16.2) occurs in many different plant species, whereas the much more complicated alkaloid brucine (D 21.3), is synthesized by only one genus of the Loganiaceae. In other words, the probabiUty that a given metabolic pathway... 

Humans are very sensitive to some types of secondary products. The bitter taste of the alkaloid brucine (D 21.3), may be recognized in concentrations of 10 %, the odor of cucumber in a concentration of 10 %. The threshold concentrations are different in different persons and depend on the physiological state even in one and the same person. 

Although the related alkaloid brucine (and possibly also vomicine [867, 868]) would appear to exhibit activity which is qualitatively identical [869] but quantitatively less potent [870], strychnine (LIII, Fig. 4) [871] can be regarded as a structurally specific drug on account of its specific action on the post-synaptic inhibitory mechanisms in the spinal cord [754, 872-881]. Indeed, so specific is this activity that the recent demonstrations [882-885] that strychnine appears to block only some of the post-synaptic inhibitory mechanisms in the cerebral cortex are open to the interpretation [882, 886-890] that the mechanisms unaffected by the drug in this location utilise a different transmitter from the transmitter involved in the spinal cord. 

Note that the resolving agent is recovered unchanged after this procedure and can be reused repeatedly. Because of the need to obtain crystalline adducts which are readily broken down to their components again, the ionic salts formed between amines and acids, either carboxylic or sulphonic, are ideal for resolution. Thus even in the last century very many amines were resolved by formation of salts with, for example, tartaric acid (16) or camphorsulphonic acid (29), while organic acids were resolved with bases such as quinine, cinchonine and the highly toxic alkaloids brucine (36) and strychnine (37). Although reliable resolution methods have now been worked out for... 

A conceptually straightforward approach to the preparation of pure enantiomers of amino acids would be resolution of their diaslereomeric salts. Typically, the amine group is first protected as an amide and the resulting prodnct is then treated with an optically active amine, such as the inexpensive alkaloid brucine (Section 25-8 and margin). The two diastereomers formed can be separated by fractional crystallization. Unfortunately, in practice, this method can be tedious and can suffer from poor yields. 

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