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QUININE

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Originally appearing in Volume V22, Page 758 of the 1911 Encyclopedia Britannica.
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QUININE , the most important See also:

alkaloid contained in See also:cinchona bark (see CINCHONA). In 1810 See also:Gomez of See also:Lisbon obtained a mixture of alkaloids which he named cinchonino, by treating an alcoholic See also:extract of the bark with See also:water and then adding a See also:solution of See also:caustic potash. In 182o Pelletier and Caventou proved that the cinchonino of Gomez contained two alkaloids, which they named quinine and cinchonine. Later quinidine and cinchonidine were discovered, and subsequently several other alkaloids, but in smaller quantity. See also:Chemistry.—The alkaloids exist in the bark chiefly in See also:combination with cinchotannic and quinic acids. The cinchotannic See also:acid apparently becomes altered by atmospheric oxidation into a red-colouring See also:matter, known as cinchono-fulvic or cinchona red, which is very abundant in some See also:species, as in C. succirubra. For this See also:reason those barks which, like C. Calisaya, C. officinalis, and C. Ledgeriana, contain but little colouring matter are preferred, the quinine being more easily extracted from them in a colourless See also:form. The exact mode of extraction adopted by manufacturers is See also:secret. That hitherto adopted by the See also:Indian See also:Government for the preparation of the cinchona febrifuge (see below) is See also:simple, but the whole of the alkaloid See also:present in the bark is not obtained by it. This method is to exhaust the powdered bark with water acidulated with hydrochloric acid and then to precipitate the alkaloids by caustic soda.

Another method consists in mixing the powdered bark with See also:

milk of See also:lime, drying the See also:mass slowly with frequent stirring, exhausting the See also:powder with boiling See also:alcohol, removing the excess of alcohol by See also:distillation, adding sufficient dilute sulphuric acid to dissolve the alkaloid and throw down colouring matter and traces of lime, &c., filtering, and allowing the neutralized liquid to See also:deposit crystals. The sulphates of the alkaloids thus obtained are not equally soluble in water, and the quinine sulphate can be separated by fractional See also:crystallization, being less soluble in water than the other sulphates. Quinine of See also:commerce is the neutral sulphate,C25H24N2O2• H2SO4.8H2O which occurs in commerce in the form of very See also:light slender See also:white acicular crystals. It is soluble in about 780 parts of See also:cold water, but in 30 of boiling water, 6o of rectified spirit (sp. gr. 0.83), and 40 of See also:glycerin. Its solubility in water is lessened by See also:sodium or See also:magnesium sulphate, but is increased by See also:potassium nitrate, ammonium chloride, and most acids. It is not soluble in fixed See also:oils or in See also:ether, although the pure alkaloid is soluble in both. It becomes phosphorescent on trituration. When prescribed it is generally rendered more soluble in water by the addition of dilute sulphuric acid or of citric acid, one drop of the former or 4ths of a See also:grain of the latter being used for each grain of the quinine sulphate. Quinine is precipitated from its solution by alkalis and their See also:carbonates. It is, however, very soluble in excess of See also:ammonia. The acid solution of sulphate of quinine is fluorescent, especially when dilute; and it is laevo-rotatory.

When a solution of See also:

chlorine is first added and then ammonia an See also:emerald See also:green See also:colour, due to the formation of thalleoquin, is See also:developed. This test answers with a solution containing only 1 See also:part of quinine in 5000, or in a solution containing not more than -4,j-6 part if See also:bromine be used instead of chlorine. The See also:fluorescence is visible in an acid solution containing 1 part in 200,000 of water. By adding an alcoholic solution of See also:iodine to a solution of the sulphate in acetic acid a See also:compound known as herapathite, 4Qu•3H2SO4.2HI•I4.6H2O, is obtained, which possesses See also:optical properties similar to those of See also:tourmaline; it is soluble in moo parts of boiling water; and its sparing solubility in cold alcohol has been utilized for estimating quinine quantitatively. The other alkaloids are distinguished from quinine thus: quinidine resembles quinine, but is dextro-rotatory, and the iodide is very insoluble in water; the solution of cinchonidine, which is laevo-rotatory, does not give the thalleoquin test, nor fluorescence; cinchonine resembles cinchonidine in these respects, but is dextrorotatory. Commercial sulphate of quinine frequently contains from I to 10% of cinchonidine sulphate, owing to the use of barks containing it. The sulphate of cinchonidine is more soluble than that of quinine; and, when i part of quinine sulphate suspected to contain it is nearly dissolved in 24 parts of boiling water, the sulphate of quinine crystallizes out on] cooling, and the cinchonidine is found in the clear See also:mother liquor, from which it can be precipitated by a solution of potassium and sodium tartrate. Samples of quinine in which cinchonidine is present usually contain a smaller percentage of water than the pure sulphate. Traces of quinidine are also some-times, though rarely, found in commercial quinine, but its presence does not detract in a medicinal point of view from the value of the latter. Owing to its voluminous See also:character as much as 18 % of water may remain present in apparently dry samples of sulphate of quinine. If it loses more than 14.6 % of water when dried at See also:loo° C. it contains an excessive amount of moisture. Owing to its variability in this respect, and to its insolubility, certain other salts have largely re-placed the sulphate in See also:modern See also:medicine.

Sulphate of quinine manufactured from cuprea bark (Remijia pedunculata) may contain from •Io to .90% of sulphate of homoquinine, which almost coincides in solubility with sulphate of quinine. Homoquinine is decomposed on treatment with caustic soda into quinine and a new alkaloid, cupreine, in the proportion of 2 to 3. Cupreine is soluble in a solution of caustic soda (differing in this respect from quinine), and therefore it is easy to prepare sulphate of quinine perfectly See also:

free from either homoquinine or cupreine. The medicinal properties of cupreine and homoquinine are of no See also:practical importance. In consequence of the high See also:price of the alkaloid an See also:attempt was made some years ago by the Government of See also:India to manufacture from cinchona bark a cheap febrifuge which should represent the alkaloids contained in the bark and form a substitute for quinine. This mixture is known as cinchona febrifuge, and is prepared chiefly from C. succirubra, which succeeds better in India than the other species in cultivation, and grows at a See also:lower See also:elevation, being consequently procurable in large quantities at a comparatively See also:low price. A mixture of the cinchona alkaloids, consisting principally of cinchonidine sulphate, with smaller quantities of the sulphates of quinine and cinchonine, is sold under the name of " quinetum " at a cheaper See also:rate than quinine. The chemical constitution of quinine and the allied alkaloids is not definitely settled, although certain relationships are well established. Thus quinine is methoxycinchonine or methylcupreine, cupreine being an oxycinchonine. These relations are shown by the formulae:—cinchonine = C19H21N2.OH; cupreine =C19H25N2(OH)2; quinine=C19H25N2(OH)(OCH3). Cinchonine yields on oxidation cinchoninic acid (y - See also:quinoline carboxylic acid). C9H6N•See also:CO2H, whilst quinine gives quininic acid, C91-15(OCH3)(CO2H).

This permits the See also:

writing of cinchonine, for example, as C9H6N•C1oHls(OH)N, the hydroxy See also:group being in the part •C1oH,5(OH)N, about which the constitution is uncertain. The subject has been especially studied by Skraup, Konigs, and von See also:Miller; Konigs and von Miller have proposed formulae consisting of a piperidine See also:ring substituted with a vinyl group; in the former that is a See also:bridge of •See also:CH2•C(OH)• from the See also:nitrogen See also:atom to the y-See also:carbon atom, connexion with the quinoline See also:residue being made at the hydroxvlic carbon atom through a •CH2• group: whilst in the latter the piperidine ring is substituted by a methyl group in addition to the vinyl group and the bridge is simply •C(OH)•, with which connexion is made as before. 37cdicine.—The sulphate is still used in medicine, and the See also:British Pharmacopeia has admitted two others, which are much more valuable—the hydrochloride and the acid hydrochloride—whilst the hydrobromide is also used. The hydrochloride—formerly known as the hydrochlorate—C20H24N202•HCl.2H2O, resembles the sulphate in See also:appearance, the crystals being, however, somewhat larger. It is soluble in less than 4o parts of cold water, and in 3 parts of alcohol (go ° o). The doses are similar to those of the sulphate, but somewhat smaller, owing to its greater solubility. The acid hydrochloride is the most valuable of all salts of quinine. It is soluble in its own See also:weight of water, and is the most rapidly and completely absorbed of all the salts of this alkaloid. It occurs in a colourless crystalline powder, having the See also:formula C2 0H24N202.2HC1.3H2O. The sulphate of quinine used in medicine may contain up to 3% of cinchonidine, but should be free from cinchonine, quinidine and cupreine. There are four pharmacopeial preparations. The See also:ferri et quininae citras, one of the " See also:scale preparations " of See also:iron, is given as a haematinic and tonic in doses of about to grains.

It is very unpleasant to take. The pharmacopeial pilule quininae contains 5 parts of the sulphate in 6. The syrupus ferri phosphatis cum quinina et strychnina (See also:

Easton's See also:Syrup) contains the of a grain of quinine in each drachm, that is, in each dose. Here the quinine acts as a See also:bitter tonic. The tinctura quininae arnmoniata or " ammoniated quinine " is made by mixing 175 grains of quinine sulphate, 2 fluid oz. of liquor ammoniae (the pharmacopeial solution of ammonia), and 18 fluid oz. of a 6o°o solution of alcohol. The dose of 1 tot drachm contains little more than a grain of quinine, the antipyretic See also:action of which is negligible. Its value in the See also:early stages of a See also:bronchitis or tracheitis is due to the ammonia. The small quantity of quinine it contains is conditioned by the solubility of the alkaloid, which is precipitated when this See also:tincture is diluted with water. No particular value attaches to the pharmacopeial preparations of the hydrochloride. Physiological Action.—Our knowledge of this subject is mainly due to See also:Professor Binz of See also:Bonn. Quinine has considerable See also:powers as an antiseptic, this See also:term defined for some See also:time as indicating the See also:power to kill bacteria. Whilst quinine possesses this power, however, it is far more potently lethal to a particular form of See also:animal organism known as the plasmodium malariae.

Against the bacteria quinine is not at all an exceptionally powerful antiseptic, though more powerful than carbolic acid. Many bacteria are killed by a .2% solution of the alkaloid. Quinine does not affect the unbroken skin, and cannot be absorbed from it, but it is slightly irritant to the See also:

pain-conducting nerves of a raw See also:surface. The first feature of the See also:internal action of quinine is its intensely bitter See also:taste. This induces a reflex secretion from the salivary and gastric glands, which is followed or accompanied by increased vascularity of the gastric mucous membrane, and by some degree of activity on the part of the See also:muscular See also:wall of the See also:stomach. This means that the appetite is strengthened, and digestion rendered more rapid and See also:complete. In this sense alone quinine is a tonic. The hydrochloric acid of the gastric juice is stated to convert any See also:salt of quinine into a chloride, and it seems probable that the absorption of quinine takes See also:place mainly from the stomach, for when the See also:drug reaches the alkaline secretions of the duodenum it is precipitated, and probably none of it is thereafter absorbed. The greater part of a dose of quinine sulphate administered by the mouth may be recovered, as a See also:rule, from the faeces, this being much the most wasteful method of giving quinine. The absorption of the acid hydrochloride is much more complete. Quinine hydro-chloride circulates in the alkaline See also:blood without precipitation, probably owing to the presence of carbonic acid in the blood. The action of quinine on the blood itself—quite apart from its action on malarial blood—is of See also:great complexity and importance.

Whilst it is not a haematinic, in that it does not increase the number of the red blood corpuscles, it very markedly influences the stability of the compounds of the haemoglobin with See also:

oxygen. Like alcohol and prussic acid, quinine interferes with oxidation, so that oxyhaemoglobin is relatively unable to give up its oxygen to the tissues, the See also:metabolism of which is therefore greatly modified. This See also:property is doubtless partly—though not wholly—explanatory of the antipyretic action of quinine. The leucocytes or white blood corpuscles are very markedly affected by quinine, the characteristic " amoeboid " movements of the cells being arrested. Hence quinine stops the See also:process of diapedesis or See also:emigration of the leucocytes from the blood-vessels into the tissues, and if applied to the extravascular spaces it arrests the leucocytic movements there. The explanation that this See also:influence on the leucocytes explained the favourable action of quinine on certain inflammatory processes nolonger holds, since we know that the inflammatory conditions are of microbic origin, and that the movements of the leucocytes are not objectionable, but highly desirable as a means of See also:defence against bacteria and their products. Quinine, therefore, is not beneficial in inflammatory conditions as far as this particular property is concerned. The action of quinine on the circulatory apparatus is not marked. It is only in very large doses that it weakens the intracardiac See also:nervous ganglia, slows and weakens the See also:pulse, and dangerously lowers the blood pressure. Similarly the depressant action on the See also:respiratory centre in the medulla oblongata occurs only after the See also:administration of enormous doses. The action of quinine on the temperature is important, for it is the safest of all known antipyretics. Its action on the normal temperature is nil.

The drug is not an antithermal. But when the temperature is raised, quinine will frequently lower it. The action is not due to any influence on the thermic centres, nor to any See also:

production of diaphoresis, but to the influence of quinine upon the stability of oxyhaemoglobin. Quinine was the first antipyretic used, and after the introduction of such preparations as antipyrin and acetanilide it may still be said to be the safest, though it is much less powerful. The maximum dose of the sulphate is about 40 grains, and of the acid hydrochloride about 25 grains. The temperature usually-begins to fall in about two See also:hours. The influence of quinine upon a malarial temperature is due to an entirely different cause (see below). In some of the lower vertebrates quinine reduces the activity of the See also:spinal See also:cord, but in the human species it appears to stimulate the nervous mechanism of the uterus under certain conditions, and it is therefore included under the class of oxytocic or ecbolic drugs. Quinine is excreted in some degree by nearly all the glands of the See also:body, but mainly by the kidneys. Traces of it may be detected in the urine within an See also:hour of its administration, and most of it is eliminated within eight or ten hours. The study of the urine is highly interesting in correlation with that of the influence of quinine upon the oxidising power of the blood, and upon the movements of the leucocytes. The amount of See also:urea, creatin, creatinin, sulphates and See also:phosphates in the urine is diminished, clearly showing that quinine exerts an inhibitory influence over the metabolic processes of the body.

This conclusion is further confirmed by the observation that the amount of carbonic acid excreted by the lungs is also diminished. The uric acid excreted in the urine (mostly in the form of urates) is markedly diminished. This product is largely derived from the nuclei of the leucocytes, which contain large quantities of the nucleo-proteids, of which uric acid is a decomposition product. It is therefore See also:

plain that the diminution of leucocytic See also:movement is to be regarded as a sign of diminished metabolism within the cells. See also:Therapeutics.—The supreme value of quinine is as a specific antidote to See also:malaria, against which it also possesses a powerful prophylactic action. Ten or fifteen grains of the sulphate are often given three times a See also:day for this latter purpose, and smaller doses of the much more efficacious acid hydrochloride will be found to convey even more certain See also:immunity. In treating malaria (including See also:ague, remittent See also:fever, intermittent fever, and all its other forms) with this drug certain important facts are to be observed. Quinine administered by the mouth or by any other means will soon enter the blood, and will then kill the haematozoon malariae, whether it be free in the blood-plasma, in the leucocytes or in the red blood corpuscles. There is one exception, however. Quinine is apparently powerless to kill the organism when it is in its reproductive phase. This phase corresponds to the pyretic attack. There is therefore no purpose to be served by administering quinine during a malarial See also:paroxysm.

Two successful methods may be adopted. The quinine may be given in a single large dose—3o grains of the sulphate, or 20 of the acid hydrochloride—an hour or two before the attack is due, i.e. just before the See also:

parent organism in the red blood corpuscles is about to See also:discharge the new See also:generation of See also:young parasites into the blood-plasma. An equally effective method, which may be combined with the above, is to give the quinine in to-grain doses of the acid hydrochloride every four hours between the attacks. Whichever method be adopted, the paroxysm that was expected will probably not appear. After a single full dose of quinine no parasites can as a rule be observed in the blood for several days. In beginning treatment, it is well to clear the hepatic and alimentary passages by a preliminary dose of See also:calomel combined with a secretory cholagogue, such as enonymin or iridin. The quinine treatment may be begun with success on the day following an attack. Quinine is much less efficacious in the treatment of See also:post-malarial symptoms, such as See also:neuralgia and haematuria, when no parasites can be detected in the blood. In such cases quinine is often inferior to See also:arsenic. Quinine is largely used as a bitter tonic in doses of about See also:half a grain. The acid hydrochloride is the best salt to employ. Quinine has some analgesic power, and is a safe and often efficient drug in the treatment of neuralgia, even when the patient has not had malaria.

Somewhat smaller doses than those given in pyrexia should be employed. Cinchonism is the name applied to the congeries of toxic symptoms which follow the prolonged administration of quinine, but may appear after one small dose in certain persons. The symptoms closely resemble those of salicylism, and also, though in less degree, those of carbolism. The patient is See also:

deaf, but complains of ringing in the ears, which may assume various forms, especially in musical See also:people. There is headache, which, with the continuance of the drug, becomes exceedingly severe, the See also:vision and See also:equilibrium are affected, and there is often some gastro-intestinal irritation. In cases where the drug has been deliberately given for its poisonous action the results are still more severe. There may be bleeding from the See also:nose, cutaneous congestion, deafness, See also:blindness, See also:coma or See also:delirium, and even See also:death from cardiac failure. After death there is found one noteworthy See also:lesion, a commencing acute inflammation of the internal See also:ear. In persons who have a marked See also:idiosyncrasy towards cinchonism, the symptoms may often be successfully averted if small doses of hydrobromic acid—lo minims of the dilute solution —are given with the quinine. A non-See also:official preparation of quinine—Warburg's Tincture—occasionally succeeds where the See also:ordinary preparations fail. The dose is I to 4 drachms. It contains 1 part of quinine in 5o.

Of the thirteen or more other ingredients, there may specially be noticed the salicylic and benzoic acids. The ,other alkaloids of cinchona bark—quinidine, cinchonidine, and cinchonine—also possess similar properties, but all are much less effective than quinine. This is also the See also:

case with the cinchona febrifuge prepared from C. succirubra. The great disadvantage of the official preparations is the bitter taste and insolubility. It is found, however, that all the soluble salts are bitter, whilst the tasteless ones are insoluble. Substitutes may therefore be divided into those administered orally and those administered hypodermically. Of the insoluble salts we may See also:notice the tannate, the propionic acid ester (euquinine) and carbonic acid ester (aristoquin), the salicylic acid ester (saloquinine); and of the soluble substitutes, quinopyrine (a compound of quinine hydrochloride and See also:antipyrine) and quinine hydrochlorocarbamide (a compound of quinine, urea and hydrochloric acid). Until 1867 See also:English manufacturers of quinine were entirely dependent upon See also:South See also:America for their supplies of cinchona bark, which were obtained exclusively from uncultivated trees, growing chiefly in See also:Bolivia, See also:Peru, and See also:Ecuador, the See also:principal species which were used for the purpose being Cinchona Calisaya; C. officinalis; C. macrocalyx, See also:var. See also:Patton; C. Pitayensis, C. micrantha and C. lancifolia. Since the cultivation of cinchona trees was commenced in See also:Java, India, See also:Ceylon and See also:Jamaica, several other species, as well as varieties and hybrids cultivated in those countries, have been used?. Later, C. lancifolia, var.

Calisaya, known as the calisaya of See also:

Santa Fe, was strongly recommended for cultivation, because the shoots of felled trees afford bark containing a considerable amount of quinine; C. Pitayensia has been introduced into the Indian plantations on See also:account of yielding the valuable alkaloid quinidine, as well as quinine. The first importation from India took place in 1867, since which time the cultivated bark has arrived in See also:Europe in constantly in-creasing quantities, See also:London being the See also:chief See also:market for the Indian barks and See also:Amsterdam for those of Java. Cinchona Calisaya has also been cultivated extensively in Bolivia and in Tolima, See also:United States of See also:Columbia. In See also:order to obtain the cultivated bark as economically as possible, experiments were made which resulted in the See also:discovery that, if the bark were removed from the trunks in alternate strips so as not to injure the cambium, or actively growing See also:zone, a new layer of bark was formed in one See also:year which was richer in quinine than the See also:original bark and equal in thickness to that of two or three years' ordinary growth. This is known in commerce as " renewed bark." The process has been found to be most conveniently practised when the trees are eight years old, at which See also:age the bark separates most easily. The yield of quinine has been ascertained to increase annually until the See also:eleventh year, at which it seems to reach its ' In Java, C. Calisaya, vars. anglica, javanica, Hasskarliana and Ledgeriana; C. officinalis, var. angustifolia; C. lancifolia, C. caloptera C. micrantha and C. succirubra. In India, C. succirubra, C. officinalis, vars. angustifolia, crispa, Uritusinga and Bonplandiana, and to a lesser extent C. Calisaya, vars. Boliviana and microcarpa; C. micrantha, C. Peruviana and C. nitida form only a small proportion of the plantations.

Since J. E. See also:

Howard pointed out that C. Pahudiana, and C. Calisaya, vars. javanica, Hasskarliana and anglica, were likely to See also:lead to disappointment as quinine-yielding species, these have been replaced in the plantations as rapidly as possible by the more valuable species, of which C. Ledgeriana, yielding from 5 to to % or even more of quinine, C. officinalis, and a hybrid between C. officinalis and C. succirubra, which has been named C. robusta, are the most important.maximum. The portion of the See also:trunk from which the bark has been removed is sometimes protected by See also:moss, and the new bark which forms is then distinguished by the name of " mossed bark." The species which yield the largest amount of quinine are by no means the easiest to cultivate, and experiments have consequently been made in See also:cross-fertilization and grafting with the view of giving vigour of growth to delicate trees yielding a large amount of alkaloid or of increasing the yield in strong-growing trees affording but little quinine. Grafting, however, has not been found to See also:answer the purpose, since the stock and the See also:graft have been found to retain their respective alkaloids in the natural proportion just as if growing separately. Hybridization also is very uncertain, and is very difficult to carry out effectually; hence the method of propagating the best varieties by cuttings has been adopted, except in the case, of those which do not strike readily, as in C. Ledgeriana, in which the See also:plants are grown from the shoots of felled trees. Some years ago it was discovered that a bark imported from See also:Colombia under the name of cuprea bark, or " hard " bark, and derived from Remijia pedunculata, Triana, and other species, contained quinine to the extent of 2 to 21%, and in 1881 this bark was exported in enormous quantities from See also:Santander, exceeding in amount the united importations of all the other cinchona barks; and by reason of its cheapness this has since that date been largely used for the manufacture of quinine. Cinchona bark as imported is never See also:uniform in quality.

The South See also:

American kinds contain a variable admixture of inferior barks, and the cultivated Indian barks comprise, under the respective names of yellow, See also:pale, and red barks, a number of varieties of unequal value. The alkaloids are contained, according to Howard, chiefly in the cellular See also:tissue next to the See also:liber. No definite knowledge has as yet been attained of the exact steps by which quinine is formed in nature in the tissues of the bark. From analyses of the leaves, bark and See also:root, it appears that quinine is present only in small quantities in the leaves, in larger quantity in the See also:stem bark, and increasing in proportion as it approaches the root, where quinine appears to decrease and cinchonine to increase in amount, although the root bark is generally richer in alkaloids than that of the stem. The See also:altitude at which the trees are grown seems to affect the production of quinine, since it has been proved that the yield of quinine in C. officinalis is less when the trees are grown below 6000 ft. than above that elevation, and that cinchonidine, quinidine, and See also:resin are at the same time increased in amount. It has also been shown by See also:Broughton that C. Peruviana, which yields cinchonine but no quinine at a height of 6000 ft., when grown at 78go ft. gives nearly as much quinine, and almost as readily, as C. officinalis. See also:Karsten also ascertained by experiments made at See also:Bogota on C. lancifolia that the barks of one See also:district were sometimes devoid of quinine, while those of the same species from a neighbouring locality yielded 31 to 4i% of the sulphate; moreover, Dr De Vrij found that the bark of C. officinalis cultivated at Utakamand varied in the yield of quinine from I to 9 %. In these cases the variation may have been due to altitude.

End of Article: QUININE

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