Alkaloids from

In the commercial extraction of alkaloids from the drugs in which they exist, the powdered drug, or an alcoholic extract of it, is treated with an alkali such as ammonia or lime to liberate the alkaloid and the alkaloid is then extracted by means of an organic solvent. The crude material thus obtained is purified and finally crystallized either as the base itself or as its water-soluble salts. 

The isolation of alkaloids from plants is reviewed in the August 1991 issue of the Journal of Chemical Education pp 700-703... 

These alkaloids include the substituted pyridone ricinine [524-40-3] (53), CgHgN202, which is easily isolated in high yield as the only alkaloid from the castor bean (Ricinus communis L.). The castor bean is also the source of castor oil (qv), which is obtained by pressing the castor bean and, rich in fatty acids, has served as a gentie cathartic. 

Bisindole Alkaloids from Tryptophan. There are two widely different types of alkaloids derived from two tryptophan (26) units. The first is a rather small group of compounds based simply on the dimers of tryptophan which includes compounds such as calycanthine (113) (Table 10),... 

The validity of this formula for ricinine was established by the same authors synthesis of the alkaloid from 4-chIoroquinoline (I). The... 

Owing to the use of lupin seeds for feeding animals, much attention has been given to the selection of species free from the more toxic alkaloids of the group, particularly sparteine, to methods of removing alkaloids from the seeds, a subjeet on which there is an extensive literature and to methods of estimating alkaloids in lupins on which a critical review has been published by Brahm and Andresen. ... 

Constitution of the Anhalonium Alkaloids. From Heffter s results it was possible to extend the formulas assigned to six of the seven anhalonium alkaloids then known as follows —... 

More interesting, as regards future developments, are the eiforts now being made to dispense with opium as an intermediate in the production of morphine. The early history of experiments in the direct extraction of the alkaloid from poppy capsules and poppy straw has been recounted by Goris and by Wiiest and Frey. ... 

The processes used in the manufacture of morphine are believed to be still based on that described by the Scottish chemist Gregory,in 1833, with improvements devised by Anderson. A description has been published by Schwyzer, who also deals with the manufactme of codeine, narcotine, cotarnine, and the commercially important morphine derivatives, diamorphine (diacetylmorphine), and ethylmorphine (morphine ethyl ether). More recently Barbier has given an account of processes, based on long experience in the preparation of alkaloids from opium. Kanewskaja has described a process for morphine, narcotine, codeine, thebaine and papaverine, and the same bases are dealt with by Chemnitius, with the addition of narceine, by Busse and Busse, and by Dott. It is of interest to note that a number of processes for the extraction and separation of opium alkaloids have been protected by patent in Soviet Russia. ... 

The total crude alkaloid from tlie soluble reineckate fraction had the low curarising potency 25 mgm./kilo frog. It consisted mainly of quaternary alkaloids and nothing crystalline lias so far been obtained from the non-quaternary portion. 

Preparation. The mother liquors from strychnine manufacture are concentrated and the alkaloids precipitated as neutral oxalates. The precipitate is dried and extracted with dry alcohol in which the strychnine salt is the more soluble. The less soluble salt dissolved in water is decolorised with charcoal, the alkaloid regenerated with ammonia and purified by crystallisation as the sulphate. According to Saunders, pure brucine may be obtained by slow crystallisation from a solution of the pure hydrochloride in alcoholic ammonia. A method of separation depending on the greater solubility in water of strychnine hydriodide was employed by Shenstone, whilst others have made use of the sparing solubility of strychnine chromate for the removal of small quantities of this alkaloid from brucine. For a large scale process see Schwyzer. ... 

The extraction of alkaloids from jaborandi has been dealt with by Wurtzen, and the estimation of pilocarpine in the drug and its preparations by Jowett and by Bourcet and more recently by Taran and by Shupe.ii Elvidge has devised a colorimetric method based on Ekkert s test, < and a polarographic study has been made by Kirkpatrick. Tlie two first-pamed authors depend on the isolation of pilocarpine nitrate, which is also the basis of the process of manufacture described by Cheninitius.12... 

Konovalova and Orekhov isolated the following four alkaloids from the roots of A. talassicum, M. Pop. 

D. datum, L. Of the three alkaloids noted by Keller in the seeds of this species, one, unnamed, was crystalline, had the formula 33 -5iOgN and m.p. 218°. According to Goodson, the seeds yield 1-7 per cent, of alkaloids from which three bases were isolated —... 

Commercial veratrine is a mixture of alkaloids prepared from sabadilla seeds and consists largely of cevadine and veratridine with some cevine. Its manufacture has been described by Schwyzer. Crystalline veratrine was first isolated by G. Merck. Wright and Luff introduced the name cevadine to distinguish this alkaloid from the commercial amorphous mixture known as veratrine. ... 

Cevadine, C32H49O9N (crystallised veratrine), was first isolated in a crystalline condition from sabadilla seeds by G. Merek, who called it veratrine, and was subsequently obtained by Schmidt and Koppen,i and by Wright and Luff, whose name cevadine has been generally adopted, though Ahrens suggested that it should be called crystallised veratrine. The yield of total alkaloids from the seeds is said to be from 6 to 7 gm. per kilo, of which 0-8 to 0-9 gm. may be obtained as crystalline cevadine, 0-5 to 0-6 as veratridine and 0-2 to 0-3 as sabadilline. 

Chou has described recently the isolation of four minor alkaloids from F. Roylei they occur in the drug to the extent of 0-001 to 0-002 per cent. 

Addendum. In a recent paper Bertho et al. have described a new process for the isolation of kurchi alkaloids. From the final residue a new base, C23H34N2, m.p. 129 5°, was isolated as the carbonate, m.p. 91° it provides the following salts B, 2HI, 2H2O, dec.) 174° B, 2HCIO4, 2.5H2O, m.p. 283°, and a mono-acetyl derivative, m.p. 254°. In a second paper Bertho, Schonberger and Kaltenbom describe further products obtained in the oxidation of conessine by chromic acid and by potassium permanganate. ... 

The same authors (1948) have isolated nicotine and the two following alkaloids from Lycopodium cernuum L. —... 

A notable change in methods of isolating alkaloids from plant materials has been described by Applezweig, depending on the use of a suitable ion-exchange material and capable of application on a semi-micro scale or for industrial use. It has been applied to the preparation of the total alkaloids of cinchona bark (totaquina) and according to Sussman, Mindler and Wood, is also used industrially for the recovery of hyoscine. 

In future a third new group will be required, according to another preliminary statement published quite recently by a team of Australian chemists, Messrs. Hughes, Lahey, Price and Webb. They have isolated six alkaloids from three rutaceous species of that country, five of which have been definitely shown to be acridine derivatives. This appears to be the fiipst-fruits of a survey of the type referred to above, which is being carried out on the Australian flora under the auspices of the Council for Scientific and Industrial Research and several of the Australian Universities. ... 

The synthesis of alkaloids from dihydronorharmane, condensation of which with o-aminobenzaldehyde gives rutaecarpine (204) 321-323), is of a particular interest. 

Evodiamine, the alkaloid from the Chinese drug plant Evodia rutaecarpa Benth. and Hook., has also been called rhetsine and its oxidation product rhetsinine, which is also found in nature, was shown to be the diamide (53). Recently a hypotensive red alkaloid isolated from the Brazilian plant Hortia arborea Engl, was given the name hortiamine. Degradation and synthetic studies have shown it to possess the structure (55). It was found together with another... 

Alkylpiperidine alkaloids from marine sponges of Haploselerida order 96MI4. 

Carboline and isoquinoline alkaloids from marine organisms 96MI5. 

Chemistry, pharmacology, and clinical efficacy of the Chinese nootropic agent huperzine A, alkaloid from Hupenia sermta with annulated 2-pyridone and l-amino-3-methyl-9-ethylidenebicyclo[3.3.l]nona-2,6-diene fragments 99ACR641. 

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