Alkaloid salts, liquid

In spite of the difficulty in definitely characterizing alkaloids by definition, they do have a surprising number of physical and chemical properties in common. For the most part, the alkaloids are insoluble or sparingly so in water but form salts (by metathesis or addition) that are usually freely soluble. The free alkaloids are usually soluble in ether or chloroform, or other immiscible solvents, in which, however, the alkaloidal salts are insoluble. This permits the isolation and purification of the alkaloids as well as their quantitative estimation. Most of the alkaloids are crystalline solids, although a few are either amorphous (coniine, nicotine, sparteine) or liquid. It is interesting to note that the liquid alkaloids have no oxygen in their molecules. Alkaloidal salts are invariably crystalline, and their crystal form and habit are often useful in their rapid microscopical identification (Sollmann, 1944). 

Colorless and odorless, clear liquid. It may mold. Incom-pat, Alkaloidal salts, hypophosphites and sulfites in acid soln salts of Fe and of most other heavy metals tannic acid. 

Alkaloids are usually basic and combine with acids to form alkaloid salts, a property often exploited to extract them from their source. Other alkaloids occur naturally as salts of organic acids. Common salts include hydrochlorides, salicylates, sulphates, nitrates, acetates, and tartrates such as morphine acetate, cocaine hydrochloride, and strychnine nitrate. Water, alcohol, and ether solutions of alkaloids and their salts are often used to administer or carry the alkaloid, particularly for medicinal purposes. Nicotine preparations can include a variety of liquid and solid mixtures of nicotine (soluble in alcohol, chloroform, ether, and water), nicotine salts, and many other nicotine compounds (e.g., nicotine sulphate and nicotine tartrate). 

Strychnicine. This alkaloid, isolated from nux-vomica leaves grown in. lava, forms needles, m.p. 240° dec.), and is characterised by the following colour reaction. When sodium hydroxide solution is added drop by drop to a solution of a salt of the alkaloid in water, the precipitate formed dissolves on addition of more alkali, forming an orange-coloured liquid which develops a violet colour on addition of hydrochloric acid. Strychnicine is scarcely poisonous, but is said to produce tetanus in frogs. 

Sempervirine, C19H1JN2. H2O. From the alkaline liquid, after removal of gelsemine by ether, Moore observed that amyl alcohol extracted two amorphous alkaloids, of which the more basie was probably Thompson s gelseminine. From this material erystalline sempervirine was obtained by Stevenson and Sayre, and later by Chou, but a formula was first assigned to it by Hasenfratz. It forms yellow needles, m.p. 228°, from ehloroform, or orange-yellow to brown-red crystals, m.p. 258-260°, from alcohol, [a]D 0°, pK value 10-6. The salts crystallise well B. HCl. 2H2O, yellow prisms, m.p. > 300° B. HBr. 2H2O, m.p. 325°... 

Contains Nitrogen.—First test the original solid ni liquid by heating in a hard-glass tube with soda-lime (p. 2), and notice if the smell is that of ammonia (ammonia salt, amide or cyanide), an amine (amine or amino-acid) or a pyridine base (alkaloid). 

True alkaloids derive from amino acid and they share a heterocyclic ring with nitrogen. These alkaloids are highly reactive substances with biological activity even in low doses. All true alkaloids have a bitter taste and appear as a white solid, with the exception of nicotine which has a brown liquid. True alkaloids form water-soluble salts. Moreover, most of them are well-defined crystalline substances which unite with acids to form salts. True alkaloids may occur in plants (1) in the free state, (2) as salts and (3) as N-oxides. These alkaloids occur in a limited number of species and families, and are those compounds in which decarboxylated amino acids are condensed with a non-nitrogenous structural moiety. The primary precursors of true alkaloids are such amino acids as L-ornithine, L-lysine, L-phenylalanine/L-tyrosine, L-tryptophan and L-histidine . Examples of true alkaloids include such biologically active alkaloids as cocaine, quinine, dopamine, morphine and usambarensine (Figure 4). A fuller list of examples appears in Table 1. 

Liquid oral antidiarrhoeals or any other dosage form for paediatric use containing diphenoxylate or atropine or belladonna including their salts and esters or metabolites, hyoscyamine or their extracts or their alkaloids. 

Corey employed a cinchona alkaloid-derived ammonium salt 5 for the solid-liquid phase transfer catalyst, and attained 99% ee in the addition of a glycine-derived imine to 2-cyclohexenone (Scheme 6) [13,14]. 

Ephedrine occurs in white, rosette, or needle crystals, or as an unctuous mass. It is soluble in water, alcohol, chloroform, ether, and in liquid petrolatum, the latter solution being turbid if the ephedrine is not dry. Ephedrine melts between 34 and 40°C, depending upon the amount of water it contains it contains not more than 0.1% of ash its solutions are alkaline to litmus it readily forms salts with acids and it responds to the usual tests for alkaloids. Ephedrine excites the sympathetic nervous system, depressing smooth and cardiac muscle action, and produces effects similar to those of epinephrine. It produces a rather long-lasting rise of blood pressure and mydriasis and diminishes hyperemia. The alkaloid may be used in 0.5 to 2% oil spray. 

Thalistyline, a monoquaternary salt from the quaternary fraction of the chloroform-soluble alkaloids of Thalictrum longistylum and T. podocarpum, has strong hypotensive action at 1.0 mg kg-1 in normotensive dogs and rabbits. It has the structure (46), and both the related bis-tertiary base and bis-quaternary salt have been isolated in small quantities from the same plants.61 The structure of (46) was determined by its fission with sodium in liquid ammonia to form the bases (47) and (48), and by its oxidation to the isoquinolone (49) and the acid (50) when it reacted with potassium permanganate.61... 

To examine the sequence II — III, two groups of whole plants of M. cordata were used, namely, ones grown under hydroponic culture in the presence of c -[V-C H3]tetrahydroberberinium salt and reference plants grown under hydroponic culture but without the radioactive compound. Every few days after administration, the liquid in alkaloid cells of the root was removed by a micro-aspiratoscope and subjected to mass fragmentography (MF). Four peaks, namely, at m/z 369 (M+ for allocryptopine), 370 ([M -I- 1]+ for allocryptopine), 372 (M+ for [V-C Hj]allocryptopine), and 373 ([M -t- 1]+ for [V-C HjJallocrypto-... 

Fig. 4. Mass fragmentograms of the liquid from alkaloid cells in Macleaya cordata root after administration of cis-lAZ-C Hiltetrahydroberberinium salt to whole plants, (a) Feeding for 21 days, (b) Reference. Conditions 3% SE-52 column (250°C constant), 5 mm x 50 cm. He 30 ml/min. Selected ions m/z 369, M + of allocryptopine m/z 370 [M + I ] + of allocryptopine mU 372, M + of (At-C2H3]allocryptopine m/z 373, [M + I) + of [Af-C Hjlallocryptopine. In this experiment ( )-cis-lN-C H,] tetrahydroberberinium salt was used.

Isotope Enrichment of Allocryptopine in the Liquid of Alkaloid Cells of Macleaya cordata Root after Administration" of cis-[A -C2H3]Tetrahydroberberinium Salt to Whole Plants... 

Codeine Sulfate, USP. Ctxleine sulfate is prepared by neutralizing an aqueous suspension of codeine with diluted sulfuric acid and then effecting crystallization. It cK Curs us white cry.stals. usually needle-like, or as a white cry.stalline powder. The salt is efflorescent and light sensitive. It is. soluble in water (1 30. 1 6.S at 80°). much less soluble in alcohol (1 1.280). and insoluble in ether or chloroform. This salt of codeine is prescribed frequently but is not as suitable os the pho.sphate for liquid preparations. Solutions of the sulfate and the phosphate are incompatible with alkaloidal reagents and alkaline sub.stances. 

Application of bis-(2-ethylhexyl) orthophosphate as a liquid ion exchanger in the complete or selective extraction of alkaloids from a buffered aqueous phase has been described. The behaviour of the salts of various alkaloids upon titration with base has been compared.Correlations have been made between the Rf of a number of alkaloids and the pH of an aqueous buffer solution which extracts half of the alkaloid from an aqueous solution. The stabilization of alkaloid solutions has been discussed. " Chromatographic separations of alkaloids by ion-exchange, adsorption, thin-layer, paper, and liquid chromatography have been reviewed. Reference lists have been compiled for methods and applications published in 1970—73 of chromatography and of electrophoresis of alkaloids on paper and thin layers. The optimum composition of Dragendorff s reagent for efficient alkaloid precipitation has been examined. ... 

Since both UC and DT proliferated well and contained a considerable amount of sanguinarine when grown in WP liquid medium at 22 °C, the effect of WP macro salts concentration on the growth and alkaloid production was studied by using either UC or DT as an inoculum (Table 23). 

When the UC was inoculated and cultured in the liquid medium, only UC was formed and no DT formation was observed. The UC growth in full, double and three-times strength macro salts WP (WP, 2WP and 3 WP) media was better than that in a quarter and a half strength macro salts WP (1/4 WP and 1/2 WP) media, but alkaloids were negligible in all the UC cultures (data not shown). Both UC and DT proliferated in the liquid medium when the DT was used as inocula (Table 23). The UC to DT ratio increased with the increasing WP macro salts concentration. 

The object of chemical extraction is to separate the psychoactive alkaloids from the plant material. This is done by first simmering the crushed plant in an acidified water bath, which converts the alkaloids into their salt form. After filtration, the plant pulp may be discarded. To extract the alkaloids from the water, the remaining liquid is made basic and an organic solvent is added. The alkaloids will migrate into this solvent, which can then be drawn off and poured into a shallow dish.The solvent will quickly evaporate, leaving behind the alkaloids in pure crystalline form (you should be so lucky ), or more commonly, as a relatively impure gummy compound. 

The acid reacts with the alkaloids in the plant material and converts them into a salt. A good way to facilitate this reaction is to simmer the acidified soup in a slow cooker overnight leave the lid on, as we don t want any liquid to evaporate. It may take two or three such operations to get all of the alkaloids into solution. Next, we strain the plant matter first through cheesecloth, then through a paper coffee filter. The bulk roughage may now be discarded because the alkaloids we seek have migrated into the aqueous solution. 

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