Like far too many aspects of modern life the production of Cocaine has gotten cruder, and more toxic over the years. Legal small-scale high quality Coca Leaf production is the only viable alternative to failed suppression strategies that have resulted in the government-sanctioned poisoning of millions of people. If you ask “who benefits” from the War on Cocaine there is only one answer – the government bureaucracies who have managed to create millions of secure jobs for themselves worldwide. All they have to do is keep managing the media, keep the legislators under control, keep their Cartel partners happy, and they can laugh all the way to their fat, happy pensions. The trail of millions of bloody bodies they leave in their wake doesn’t bother them one bit.
For a detailed look at the crude, toxic methods and materials used by the drug cartels in producing the Cocaine that sells on the streets of the US and Europe, check out http://www.deamuseum.org/ccp/coca/production-distribution.html
Yes that’s a DEA website, with full instructions on how the bad guys make Cocaine. DEA likes to show off and mock the primitive methods used by the cartels. As if they aren’t knuckle-draggers themselves.
Also let’s remember that the cocaine cartels are forced into those crude jungle labs by the DEA drug Nazis, where all they have access to for the most part is primitive equipment and materials. But big joke – that’s all anyone really needs to produce a white (well, off-white really) powder ready for snorting by people who for the most part could care less about purity and quality as long as they get the buzz they’re seeking.
In my opinion poisoned Cocaine is an avoidable tragedy of monstrous proportions created and maintained by world governments that has resulted in the destruction of millions of lives. The enforcers of narcotics laws worldwide are fully complicit in the slaughter, and in spite of their self-righteous bullshit they know it, and the sickest of them get sexually aroused when they think about “enforcing the law”.
But all that is 100% about Cocaine – not Coca leaf.
The world of Mama Coca wasn’t always this way. Although readers of this blog know that I have no particular interest in Cocaine, since its relevance to health and healing is minimal when compared with the pure, natural Coca Leaf from which it is derived, it may be of interest to readers to discover that today’s Cocaine bears only a chemical resemblance to the Cocaine that was being produced in the 1800’s by pharmacy labs and even by doctors themselves for their patients.
Quality and purity were the primary concerns and since there weren’t any drug Nazis busting down doors Cocaine labs could focus on those higher concerns rather than having to huddle in the jungle and drink kerosene for lunch while brewing “who gives a shit” Cocaine.
So here I’m offering a chapter on Cocaine manufacturing from “The History Of Coca” by Dr. William Golden Mortimer (1901) which is available in its entirety my E-Book “The Coca Leaf Papers”.
Fair warning; what follows here is pretty detailed – not a 3-minute quick read.
CHAPTER X: THE PRODUCTS OF THE COCA LEAF
“Nor Coca only useful art at Home,
A famous Merchandize thou art become;
A thousand Paci and Vicugni groan
Yearly beneath thy Loads, and for thy sake alone
The spacious World’s to us by Commerce Known.” –Cowley.
Search For The Secrets Of The Coca Leaf
Of all the problems in the study of Coca the search for the force producing qualities of the leaf is the most profound. Science, ever alert to trace with exactitude the secrets of Nature, has struggled in vain to isolate and explain this hidden source of energy. But so cleverly are the atoms associated which go to build up the molecules of power in this marvelous leaf, that though the chemist through the delicacy of analysis has from time to time placed these atoms in differing groups and thus often given to the world some new combination, the one sought element of pent-up endurance inherent in Coca has remained concealed. It is like the secret of life – though known to be broadly dependent on certain principles which may readily be explained, the knowledge of the one essential element remains as great a secret as before research began.
Though all the accounts of travelers had directed attention to the peculiar qualities of Coca in sustaining strength, at the period when the first knowledge of this leaf reached Europe chemistry was not sufficiently advanced to admit of an exact analysis of plant life. Indeed, science met with little encouragement when the great powers were engrossed in political preferment, and it was not until the latter part of the eighteenth century that an impetus seemed given to research after Lavoisier had laid the foundation for modern chemistry. Though he lost his life on the guillotine through the whirligig of political fate during the French Revolution, just as he was at the height of his labors, a new interest was established and the work of the French chemists became active.
Humboldt was then making his extensive explorations through South America, collecting data which was to serve as a basis of research during many subsequent years. Cuvier, the anatomist, was advancing his theories on the classification of animals; Fraunhofer had established a means for studying the heavenly bodies through the spectrum, while chemical electricity had progressed from the experiments of Volta to the electromagnet of Ampere.
The method for expressing chemical equations, such as are now shown by those symbolic letters and figures which appear to the uninitiated as so many hieroglyphics, was not understood until Dalton, in 1808, had perfected his law of proportions. This was an important advance in chemical knowledge, for from it was built up the sign language which in a chemical formula expresses not only the symbol of each element, but tells the chemist the relative proportion of the combining atoms.
These fundamental facts are of interest as bearing upon the chemical history of the Coca leaf, while the combining nature of atoms has suggested an interesting theory that the physiological action of a chemical medicine is influenced by its molecular weight. This has been a matter of discussion among physiological chemists for years, and was suggested by Blake as long ago as 1841 and since by Rabuteau. Thus an element of a fixed atomic weight may have special reference to the muscular system, while another of different weight may act upon the nervous tissue – qualities which are fulfilled in the action of the several Coca bases.
Early Clues & Misdirections
Boerhaave may be said to have been the father of the present system of organic chemistry in the early part of the eighteenth century. So important were his teachings held that his works were translated into most modern languages. Although his attempts at analysis of living things attracted a wide interest, they could be in no manner exact, because the fundamental elements entering into the composition of all organic structure – carbon, hydrogen, oxygen and nitrogen – had not then been determined. Yet so skilled were his observations, even under limited opportunities, that many of his conclusions have not since been refuted in the light of improved methods. Perhaps the earliest hint upon alkaloids was that made by this scientist when he referred to the bitter principle in the juices from chewing Coca as yielding “vital strength” and a “veritable nutritive.”
It was reserved for Liebig some hundred years later to perfect the science of living structures, and to show there was not that exact separation between the chemistry of the organic and inorganic world that had previously been supposed. Following the teachings of this master mind, many compounds were constructed in the laboratory synthetically, and urea was thus produced in 1828 by Woehler, whose name is associated with the early investigators upon cocaine. Research upon the chemistry of organic bodies was now active. In England the work of Davy upon soils and crops, and the investigations of Darwin, unfolded in his theory of the origin of species, gave a new meaning to the study of organic life.
It was but a natural outcome of this spirit for research that turned the attention of explorers to South America, which had remained practically a new world since its discovery. Here were to be found innumerable strange plants indigenous to a country where everything was marvelous when viewed with the comparative light of the older world. In the height of this interest, the suggestive hints of naturalists and travelers were incentives to further the investigations of the European chemists. The writings of Cieza, Monardes, Acosta, Garcilasso and a host of others upon the wonderful qualities of the Coca leaf, stimulated a desire to solve its tradition of ages and prove its qualities by the test of science.
It is surprising to now look back over three centuries and recall these early authors, to consider under what conditions they wrote, and to read with what enthusiasm and exactness they gave expression to the knowledge they had gained from an observation of the novel customs about them. Thus the Jesuit father, Blas Valera, speaking of the hidden energy of Coca, wrote: “It may be gathered how powerful the Cuca is in its effect on the laborer, from the fact that the Indians who use it become stronger and much more satisfied and work all day without eating.”
It was not until after Coca had been botanically described by Jussieu, and classified by Lamarck, that its chemical investigation approached thoroughness. The researches of Bergmann and Black upon “fixed air” – as carbonic acid was then termed, the discovery of hydrogen by Cavendish, of nitrogen by Rutherford and of oxygen by Priestley, each following upon the other in quick succession in the latter half of the eighteenth century, displayed the great activity of chemistry at that period. Although no result was then arrived at in the investigations upon Coca, the spirit of the time was eminently toward exactitude, and this was displayed in many endeavors to trace to a chemical principle the potency of the Coca leaf.
Attention was very naturally directed to the method in which Coca was used, and the llipta which was employed with the leaves in chewing was looked upon as having some decided influence. Dr. Unanue, who has written much concerning the customs of the Indians, was one of the first to suggest that possibly this alkaline addition to the leaf developed some new property to which the qualities of Coca might be attributed, while Humboldt, as elsewhere referred to, through an error of observation considered this added lime as the supposed property of endurance.
Stevenson, in 1825, described the action of the llipta as altering the insipid taste of the leaves so as to render them sweet, and in 1827 Poeppig expressed the opinion that there was a volatile constituent in the Coca leaf which exposure to the air completely destroys.
Attention had now been directed to the isolation of alkaloids from plants, and during the first quarter of the nineteenth century several active principles were thus obtained and the possibility of tracing the hidden properties of Coca through analysis was suggested. Von Tschudi, when engaged in his extended explorations through Peru, became so impressed with the qualities of Coca that he advised Mr. Pizzi, Director of the Laboratory Botica y Drogueria Boliviana at La Paz, to examine the leaves, which resulted in the discovery of a supposed alkaloid, but when on his return to Germany this body was shown to Woehler, it was found to be merely plaster of paris, the result of some careless manipulation.
Dr. Weddell, in 1850, after a prolonged personal experience in the Andes with the sustaining effects of Coca, pronounced it as yielding a stimulant action differing from that of all other excitants. This influence both he and other observers supposed might be due to the presence of theine, the active principle of tea, which had shortly before been discovered, and was then exciting considerable discussion. With this idea in view, Coca leaves were examined, and, though this substance was not found, there was obtained a peculiar body, soluble in alcohol, insoluble in ether, very bitter, and incapable of crystallization, and a tannin was obtained to which was attributed the virtues of Coca.
About this same period there was found in the leaves a peculiar volatile resinous matter of powerful odor, and two years later, from a distillation of the dry residue of an aqueous extract of Coca, an oily liquor of a smoky odor was separated together with a sublimate of small needle-like crystals, which was named “Erythroxyline,” after the family of which Coca is a species. So each new investigator made a little progress, and in 1857 positive results were very nearly reached through the following process: An extract of Coca was made with acidulated alcohol, the alcohol was expelled, and the solution rendered alkaline by carbonate of soda. Upon extracting this with ether, an oily body of alkaline reaction was obtained without bitter taste, which on application to the tongue produced a slight numbness. The reaction of platinum chloride yielded with the acid solution a yellowish precipitate, soluble in water. From a distillate of the leaves with alkali there was remarked a disagreeable, strongly ammoniacal odor. Subsequently a peculiar bitter principle, extractive and chlorophyl, a substance presumed to be analogous to theine, and a salt of lime was found.
These negative findings led some to assert that Coca was inert and its properties legendary, but more careful observation has shown the true difficulty was an inability to secure appropriately preserved leaves for examination. This was made evident through an essay upon Coca by an eminent Italian neurologist, from experiences while a resident of Peru, when a host of physiological evidence emphasized the powerful nature of Coca, wholly apart from any mere delusions of fancy or superstition. The weight of facts presented proved sufficiently forcible not only to stimulate the waning spirit for scientific inquiry, but to awaken a widespread popular regard in what was now generally accepted as a plant of phenomenal nature.
In the height of this interest Dr. Scherzer, who accompanied the Austrian frigate Novara on the expedition to South America, opportunely brought home specimens of Coca leaves from Peru. These were sent to Professor Woehler of Gottingen for analysis, who entrusted their examination to his assistant, Dr. Albert Niemann, who is regarded as the discoverer of the alkaloid cocaine. Thus this chemist entered upon the investigation of Coca not a mere accidental way, but with an understanding of the seriousness of his research and its probable importance.
The “Aha” Moment That Led To Cocaine
Niemann exhausted coarsely ground Coca leaves with eighty-five per cent, alcohol containing one-fiftieth of sulphuric acid; the percolate was treated with milk of lime and neutralized by sulphuric acid. The alcohol was then recovered by distillation, leaving a syrupy mass, from which resin was separated by water. The liquid then treated by carbonate of soda to precipitate alkaloid emitted an odor reminding of nicotine, and deposited a substance which was extracted by repeatedly shaking with ether, in which it was dissolved, and from which the ether was recovered by distillation. There was found an alkaloid present in proportion of about one-quarter of one percent, which was named “Cocaine” after the parent plant, and the chemical formula C32H20NO8, according to the old notation, was given it. Mechanically mixed with its crystals there was a yellowish-brown matter of disagreeable narcotic odor, which could not be removed with animal charcoal or recrystallization, and was only separated by repeated washings with alcohol.
Pure cocaine, as described by this investigator, is in colorless transparent prisms, inodorous, soluble in seven hundred and four parts of water at 120 C. (53.60 F.), more readily soluble in alcohol, and freely so in ether. Its solutions have an alkaline reaction, a bitter taste, promote the flow of saliva and leave a peculiar numbness, followed by a sense of cold when applied to the tongue. At 980 C. (208.40 F.) the crystals fuse and congeal again into a transparent mass, from which crystals gradually form. Heated above the fusing point, the body is discolored and decomposes, running up the sides of the vessel. When fused upon platinum the crystals burn with a bright flame, leaving a charcoal which burns with difficulty. The alkaloid is readily soluble in all dilute acids forming salts of a more bitter taste than the uncombined cocaine. It absorbs hydrochloric acid gas, fuses and congeals to a grayish white transparent mass which crystallizes after some days. The crystals from its solution are long, tender and radiating.
Besides cocaine, there was found in the alcoholic tincture precipitated by milk of lime a snowy white granular mass. This fused at 700 C. (1580 F.), was slowly soluble in hot alcohol, more readily so in ether, and was not acted on by solutions of acids or alkalies. This substance was named Coca wax and given the empirical formula C66H66O4.
Upon distilling one hundred grammes of leaves, a slightly turbid distillate was obtained, which when redistilled with chloride of sodium, yielded white globular masses lighter than water and having the peculiar tea-like odor of Coca.
In the dark red filtrate from which the cocaine had been precipitated by carbonate of soda there was found after suitable treatment a Coca tannic acid to which the formula C14H18O8 has been given. This latter result, it will be remembered, was as far as Wackenroder’s investigations had gone in 1853.
The atomic weight of the amorphous compound determined from the double salt with chloride of gold, was found to equal 283, and when crystallized from hot water 280, or from alcohol 288. On heating this double salt benzoic acid was sublimed from it, which was recorded as the first observation of this nature from any known alkaloid.
Chemists Go Crazy Over The “Magic Bullet”
Following this research, the late Professor John M. Maisch of Philadelphia verified the several results. The small percentage of nitrogen announced in the original formula suggested that possibly cocaine was a decomposition compound, while the nicotine odor was thought to result from a nitrogenous body or another alkaloid. To determine this, the liquor and precipitate which had been obtained by carbonate of soda were distilled over a sand bath. A syrupy liquid was left, from which the alkaloid was separated by ether, while from the distillate was collected a resin-like mass of an acrid taste, having a narcotic odor, soon lost on exposure to a damp atmosphere, while the mass became acid and was now rendered easily soluble in water and alcohol. Whether or not this principle was nitrogenous this investigator left undecided.
Continuing the same line of research as that of Niemann, and following the suggestions of Maisch, William Lossen of Gottingen carried out an extended inquiry as to the nature of cocaine, and established its formula C17H21NO4, in accordance with the new notation. In examining its composition he found by heating it with hydrochloric acid that it was split up into benzoic acid and another body, thereby confirming the observation which had been made concerning this sublimation from the double salt of chloride of gold and cocaine. This new base he named “ecgonine,” from the Greek for son or descendant.
The breaking down of cocaine was subsequently shown due to hydration, by saponifying it with baryta, and also with water alone. The first change being into benzoyl-ecgonine, followed by a sublimation of benzoic acid, while from the syrupy residue the ecgonine may be separated by repeated washings with alcohol and precipitation with ether. The crystals being only dried with great difficulty.
Ecgonine, C9H15NO3, crystallizes over sulphuric acid in sheaves. It has a slight bitter-sweet taste, is readily soluble in water, less so in absolute alcohol, and insoluble in ether. Heated to 1980, it melts, decomposes and becomes brown. It forms salts with the acids, most of which crystallize with difficulty. With alkalies, it forms crystallizable combinations soluble in water and alcohol. In aqueous solutions the hydrochloride yields no precipitate with alkalies. Chloride of platinum in presence of much alcohol gives an orange yellow precipitate, chloride of mercury throwing down a yellow precipitate under the same conditions.
The unstable nature of cocaine in the presence of acids has suggested their avoidance in its preparation, plain water being considered preferable. In this process Coca leaves are digested several times at 1400 to 1760, the infusions united, precipitated by acetate of lead, and filtered. The lead is removed by the addition of sulphate of soda, and the liquor concentrated in a water bath. Carbonate of soda is then added, and the whole shaken with ether to dissolve the alkaloid, when the ether may be recovered by distillation.
In his researches Lossen also described the liquid alkaloid that had been hinted at by Gaedcke in 1855, and subsequently noticed by Niemann and Maisch, which, at the suggestion of Woehler, who was associated in this investigation, was termed ”hygrine”, from vypos – liquid, to which the formula C12H13N was given. This was obtained by saturating the slightly alkaline mother liquor from which cocaine had been extracted with carbonate of soda and repeatedly washing with ether. Evaporation of the ethereal extract left a thick yellow oil of high boiling point with a strong alkaline reaction.
Hygrine thus found is described as very volatile, distilling alone between 140° and 230° F. It is slightly soluble in water, and more readily so in alcohol, chloroform and ether, not in caustic soda, but readily in dilute hydrochloric acid. Its taste is burning and it has a peculiar odor similar to trimethylamine or quinoline. The oxalate and muriate are crystallizable, but very deliquescent.
With chloride of platinum, hygrine gives a flocculent amorphous precipitate which decomposes on heating. Bi-chloride of mercury gives an opalescence, due to the formation of minute oily drops.
Thus far there had been found in Coca leaves a crystallizable compound of unstable composition – cocaine; a second base which was only to be crystallized with difficulty – ecgonine; an intermediate compound – benzoyl-ecgonine; and an oily volatile liquid of peculiar odor – hygrine; together with Coca-tannic acid, and a wax-like body. Meantime, considerable was done in a physiological way in experimenting with the new alkaloids, though little decided progress was made during the following twenty years, until 1884, when the use of cocaine in local anӕsthesia was announced. The importance of this application occasioned an increased activity of investigation regarding the Coca products. This interest tended to make our knowledge of the alkaloids more exact, as well as to enrich our understanding of those inherent sustaining properties of Coca which have for past ages excited wonder.
Entrepreneurs Capitalize On The Discovery
In the early days of the cocaine industry some manufacturers asserted that the several associate substances found in Coca leaves were decomposition products, developed by changes taking place in deteriorating leaves or arising during the process of obtaining the one alkaloid. The great demand for cocaine and the high price it commanded generated an apparent unwillingness on the part of manufacturers to admit the possible presence in Coca of any other principle than cocaine. Processes innumerable were devised to force the greatest yield of alkaloid from the leaves, and some of the earlier specimens of the salt placed upon the market were more or less an uncertain mixture, dirty white in color and having a nicotine-like odor. This was defended as a peculiarity of the substance, the therapeutic action of which was asserted to be identical with cocaine, even though the appearance was not so elegant as the purer crystals. An endeavor to purify the salt by studying its sources of decomposition resulted in the separation of several important alkaloids.
The intermediate base benzoyl-ecgonine C16H19N04, was described as a by-product of the manufacture of cocaine, and it has been shown may be also obtained by the evaporation of cocaine solutions. It has been prepared by heating cocaine with from ten to twenty parts of water in a sealed tube at 90° to 95° C, with occasional shaking until a clear solution is obtained. This is extracted with ether to remove all traces of undecomposed cocaine, and then concentrated on a water bath and crystallized over sulphuric acid. The crystals form as opaque prisms or needles, sparingly soluble in cold water, more readily so in hot water, acids, alkalies and alcohol, while insoluble in ether. It melts at 90° to 92° C, then solidifies, and again melts at about 192° C. The taste is bitter, its solutions are slightly acid, becoming neutral after recrystallization. The hydrochloride, at first of a syrupy consistency, forms tabular crystals which are freely soluble in absolute alcohol. Mayer’s reagent produces a white, curdy precipitate; iodine in potassium iodide, a kermes brown precipitate; chloride of gold, a bright yellow precipitate, soluble in warm water and alcohol.
It will be recalled that Maclagan, Niemann and Maisch had each alluded to an uncrystallizable residue in their processes of extraction, and an effort was made to definitely determine its true quality. But just as cocaine was at first regarded as the only alkaloid, so this amorphous substance was studied as a whole instead of being regarded as a mixture of bases. Coca leaves, it was asserted, contained a crystallizable cocaine and an uncrystallizable cocaine. The latter product has been named cocaicine, cocainoidine and cocaminey and is still the subject of investigation.
The relative amount of this non-crystallizable body left in the mother liquor after the precipitation of cocaine varies greatly and is wholly dependent upon the kind of leaves used, or the processes to which they are subjected. The color of various specimens varies from dark yellow to dark brown, while the consistence is from that of a syrupy liquid to a sticky, tenacious solid, which, after spontaneous evaporation, may form short, fine crystals. The odor, while recalling nicotine, is more aromatic and less pungent; the taste bitter and aromatic. This body is of alkaline reaction, soluble in alcohol, ether, benzole, chloroform, petroleum ether, acetic acid, etc., and of varying solubility in water, according to its consistence. On gently heating it becomes quite fluid. It is very soluble in dilute acids, with which it forms non-crystalline salts, all of which dissolve readily in water. Dissolved in rectified spirit and treated with animal charcoal or acetate of lead, to precipitate the coloring matter, a pale yellow, sticky, non-crystalline body is obtained, which will not form crystals, even after standing for months. Solutions of the substance in alcohol, repeatedly precipitated by ammonia, yield a nearly white non-crystalline flocculent body, which is very hygroscopic, the original odor and taste remaining, no matter how often the purifying process is repeated. Evaporated at gentle heat, the solutions darken, and if evaporated to dryness the substance becomes insoluble in water. The precipitation with permanganate of potash is brownish, which, on heating, yields an odor of bitter almonds; 5 c.c. of a solution 1-1000 reduces 20 to 40 drops of a permanganate solution of the same strength.
Professor Stockman, of Edinburgh, made an interesting study of these mixed bases, which he originally supposed to be a solution of ordinary crystalline cocaine in hygrine, basing his conclusions on the physiological action and chemical relations. As he stated, cocaine is extremely soluble in hygrine, and once solution has occurred it is practically impossible to separate the two bodies, as they are both soluble in the same menstrua and are both precipitated by the same reagents.
This is also the case with the salts of these bodies, though not to the same extent, the presence of hygrine rendering any such samples of the salt hygroscopic, as well as imparting the peculiar nicotine-like odor of hygrine. Subsequent investigation, however, has convinced this physiologist that the substance he experimented with was cocamine dissolved in hygrine, together with some benzoyl-ecgonine.
Thus it will be seen that the earlier conclusions regarding the Coca products were erroneous from imperfect knowledge. With the increasing usefulness of cocaine this confusion is a serious matter, because these mis-statements of the chemists and physiologists are often still quoted as authoritative. So positive were some of these earlier opinions that even after physiological proof showed the unmistakable presence of associate alkaloids with cocaine they were asserted, from interested motives, to be poisonous contaminations. In the face of this the result of physiological experimentation with the various Coca bases indicate that they are all more mild than cocaine, from which they differ markedly in physiological action. Dr. Bignon, Professor of Chemistry at the University of Lima, Peru, who from position and opportunities may be regarded as a competent authority upon Coca, long since asserted, when grouping the alkaloids of Coca in two classes, that the crystalline body is inodorous, while the non-crystalline has a peculiar odor and is weaker in action and less poisonous than the crystallizable cocaine.
Where Most “Magic Bullet” Hunters Went Astray
The wholly different action of cocaine therapeutically from the Coca leaves of the Andean, or the more exact scientific preservations of Coca such as exhibited in the preparations of M. Mariani – which fully represents the action of recent Peruvian Coca, clearly indicates the presence of certain important principles in Coca, the properties of which are sufficiently distinct to markedly effect physiological action in a manner different from any one of its alkaloids. Happily we are now learning more definitely through research and experimentation, and these earlier errors are being corrected.
The diametrically opposite findings of investigators of known repute indicate that these inharmonious conclusions were not wholly the result of carelessness nor prejudice. Just as Coca experimented with by one observer repeated the traditional influence, or in some other instance proved inert, so the chemists found the result of their labors at variance. Much of this confusion was cleared away when the botanists explained that there are several varieties of Coca. Those qualities which had formerly been attributed to superstitious belief, or which when reluctantly accepted as possibly present in an extremely fugitive form which was lost through volatility, were shown to be dependent upon the variety as much as upon the quality of the Coca leaf employed in the process of manufacture.
Cocamine, C19H23N04, was originally studied in the alkaloids obtained from the small leaf variety of Coca by Hesse. It was regarded by Liebermann as identical with a base which he described as y-isatropyl-cocaine and afterward termed a truxilline, because supposedly found only in the Truxillo variety of Coca.
The research leading to these conclusions provoked bitter controversy between these two investigators. It has since been determined that cocamine is of the same empirical composition as cocaine, though weaker in anaesthetic action. It is a natural product of several varieties of Coca, particularly of that grown in Java. From hydrolysis by mineral acids cocamine yields cocaic, iso-cocaic and homo-iso-cocaic acids, while from its isomeride there is formed in a similar way alpha-isotropic or beta-truxillic acid. Both cocaic and iso-cocaic acids yield cinnamic acid and other products on distillation. Subsequently a similar body was prepared synthetically from ecgonine and cinnamic anhydride, and named cinnamyl-cocaine. It forms large colorless crystals, melts at 1200, is almost insoluble in water, and readily soluble in alcohol and ether. This body has been proved to occur naturally in Coca leaves from various sources, being present in some specimens as high as 0.5 per cent.
Thus it will be seen there has been much discussion and uncertainty upon the Coca products, particularly so as to those of an oily nature, originally designated as hygrine and the amorphous substances previously described under various titles.
It is the opinion of Hesse that hygrine is a product of decomposition of one of the Coca bases, and does not occur in fresh Coca leaves; in support of which he asserted that while dilute acid solutions of hygrine have a strongly marked blue florescence which is characteristic, this reaction is not shown when fresh leaves are first operated upon. But as this reaction develops gradually, he inferred that hygrine was formed by the decomposition of amorphous cocaine, from the solution of which it could be separated by ammonia and caustic soda as a colorless oil having the odor of quinoline. In fact, he considered the oil thus obtained a homologue of quinoline, possibly a tri-methyl-quinoline.
Another observer, while experimenting with the alkaloids of Coca by means of their platinum salts, obtained an oily base, exceedingly bitter and differing in odor and solubility from that which had been described by Lessen, but which was presumably identical with the amorphous products, cocaicine and cocainiodine, and Hesse concluded there might really be two oily bases in amorphous cocaine, one found in the benzoyl compounds of the broad leaf variety and one in the cinnamyl compounds of the Novo Granatense variety, in both cases associated with cocamine and another base, which he named cocrylamine. Liebermann, on the other hand, considers hygrine a combination of two liquid oxygenated bases which may be separated by fractional distillation. One – C8H15NO, an isomeride of tropine, with a boiling point 1930 to 195°, the other, C14H24N20, not distilling under ordinary pressure without decomposition, while still other experimenters from distilling barium ecgonate obtained a volatile oily liquid which strongly resembles hygrine. Merck has shown this body yields, on decomposition, methylamine, from which it has been inferred that it is identical with tropine, and hence closely allied to atropine. With this fact in view it was presumed the dilating property of cocaine upon the pupil was due to hygrine, but this has been proved not to be the case.
The assertion that hygrine is never present in Coca leaves, but is merely a decomposition product in the manufacture of cocaine, lends an added interest to the research of Dr. Kusby upon fresh Coca leaves made while he was at Bolivia. From repeated examinations he found a certain yield of alkaloids, while specimens of the same leaves sent to the United States yielded from treatment by the same process less than half the percentage of alkaloid that he had obtained. This prompted him to search for the possible source of error, and it was found that after all the cocaine was eliminated there was still a decided alkaloidal precipitate. From this it was concluded that: “native Coca leaves contain a body intimately associated with the cocaine and reacting to the same test, which almost wholly disappears from them in transit.”
This result indicates the presence in Coca leaves of some extremely volatile principle to which decided physiological properties are attached, which may also be obtained from suitably preserved leaves. When a preparation made from recent leaves in Bolivia was submitted to Professor Remsen, of Johns Hopkins University, his assistant reported that he found a bitter principle, and an oil, which presumably differed in no way from that found at the time of the examinations made in Bolivia. This is comparable with similar findings of those who have experimented with Coca, whether the leaves were recent and examined on the spot, or the examination had been made thousands of miles distant upon well preserved leaves. In each instance similar volatile alkaloids have been obtained, which have commonly been pronounced “decomposition products,” yet, as these are always found by careful observers, it indicates they are the natural associate bases of Coca.
The conclusions are that crude cocaine is not merely a single alkaloid. As the yield of crystallizable cocaine from the crude alkaloid varies from fifty to seventy-five percent, the associate alkaloids, together with the impurities and contaminations of manufacture, must constitute the remaining twenty-five or fifty percent, of the substance. Though our knowledge of these alkaloids is not yet exact, each of them has been found to possess certain chemical characteristics and sufficient physiological influence to prove a factor in the action of Coca. While these several Coca bases have been experimented with physiologically to a limited extent, they have never been individually applied to therapeutic uses. They have been regarded by the manufacturers of cocaine as simply so much waste from their yield of cocaine, and the attention of chemists has been directed to converting them by some synthetic process to what has been regarded as the pure alkaloid.
In the chemical constitution of cocaine there is a methyl, CH3, and a benzoyl, C6H5CO2, radical, either of which can be replaced by other acid radicals and so give rise to various homologues – or compounds of similar proportions. The methyl radical has been shown to be essential to the anӕsthetic action, and its presence or absence in the chemical group constitutes a poisonous or non-poisonous Coca product. By heating the Coca bases with alkyl iodides the corresponding esters are obtained. Thus methyl-benzoyl-ecgonine (cocaine); ethyl-benzoyl-ecgonine (homococaine); methyl-cinnamyl-ecgonine (cinnamyl-cocaine), etc., are formed. Acting upon this data, Merck, by heating benzoyl-ecgonine with a slight excess of methyl-iodide and a small quantity of methylic alcohol to 100° C, evaporating the excess of methyl-iodide and methylic alcohol, obtained a syrupy liquid containing cocaine hydriodate, from which an artificial cocaine was produced. In a similar way Skraup, by heating benzoyl-ecgonine, sodium-methylate and methyl-iodide in a sealed tube, made a synthetic cocaine, although the yield was only about four percent, while that of Merck was nearly eighty percent of the theoretical quantity.
In following this process, but using ethyl iodide, Merck obtained a new base, or homologue, cocethyline, or homococaine, with the formula C18H23NO4, which crystallizes from ether in colorless, radiating prisms, and from alcohol in glossy prisms, which melt at 1080 – 1090 C. The alkaloid is sparingly soluble in alkalies; chloride of gold gives a voluminous yellow precipitate, and chloride of mercury a white, pulverulent one, soluble in hot water. Falck has ascertained that cocethyline has an anӕsthetic action similar to cocaine, though weaker.
In following a similar method, but employing propyl iodide and propyl alcohol, and again by the use of iso-butyl-iodide with its corresponding alcohol, coc-propyline and coc-iso-butyline have been respectively formed, both of which have a strong anaesthetic action, and, though chemically different, exhibit the same reactions as cocaine.
Ecgonine has been converted into a new base by heating it for twenty-four hours with aqueous potash. This differs from ecgonine by being less soluble in absolute alcohol, in having a higher melting point, and in being dextro-rotary, and hence termed dextro-ecgonine. From this there has been prepared synthetically a dextro-cocaine, a colorless oil which solidifies and forms crystals on standing which are readily soluble in ether, alcohol, benzine and petroleum spirit. This body resembles cocaine, but its action is more fugitive.
Patenting The Magic Bullet – And Ignoring The Divine Leaf
From the ready conversion of the various Coca bases experimentally it was but a step to the building up of the associate bases into a synthetic salt of cocaine. This has given rise to a profitable industry, the process for which has been patented in Germany. In this process the mixed bases are converted by hydrolysis to ecgonine, then to a solution of hydrochloride of that salt in methyl alcohol. The hydrochloride of ecgonine methyl-ester is formed, and from this the salt is crystallized and heated over a water bath with benzoyl chloride, the homogenous mass being washed and separated from benzoic acid, and the cocaine precipitated with ammonia and crystallized from alcohol.
(From) American Druggist, January 1889
As is well-known, coca leaves, upon extraction, do not yield at once pure cocaine. The latter is always accompanied by a number of amorphous secondary alkaloids, which have to be separated before pure, crystallized cocaine can be obtained.
The nature of one of those secondary alkaloids has recently been cleared up by one of the authors of the present paper. As a general result of the preliminary studies, it was found that all the amorphous alkaloids, upon being boiled with acid, yield the base ecognine. The latter is very easily obtained by boiling the alkaloids for about one hour with hydrochloric acid, filtering off the separated acids (benzoic, etc) evaporating the acid filtrate to dryness, and boiling the dry residue with alcohol to remove further portions of benzoic or other acids. Pure hydrochlorate of ecognine is left behind.
The base is set free with soda, and purified by recrystallization from alcohol. Ecognine thus obtained was found to be absolutely identical with ecognine derived from crystallized cocaine.
It now became a question whether ecognine could not be converted back into cocaine by some simple, practical process. Between ecognine and cocaine there is an intermediate base, benzoyl-ecognine, which consists of ecognine in combination with the benzoyl nucleus. Heretofore benzoyl-ecognine had only been obtained either as a companion of cocaine or as a [product of the decomposition of the latter, but never as a synthetic product. This synthesis has now been accomplished by the authors and the gap between ecognine and cocaine thereby bridged over.
The problem was how to cause the benzoyl nucleus to combine with the ecognine. This was easily accomplished by means of anhydrous benzoic acid (benzoic anhydride) as well as by benzoyl chloride. The following method is given by the authors from their patent dated August 17th, 1888.
Make a hot saturated solution of ecognine ( one molecule) in about half its weight of water, and digest it at the temperature of the water bath for about one hour with somewhat more than one mol. Of benzoic anhydride added gradually. The n set it aside. It will solidify on cooling or standing, or while being agitated with ether, which is required to remove the excess of the benzoic anhydride added and the benzoic acid formed. The benzoyl-ecognine which has been formed, as well as any unaltered ecognine, are almost insoluble in ether and remain behind. The ethereal solution, upon evaporation, leaves behind all the benzoic acid used in excess. In order to obtain the synthetic benzoyl-ecognine pure, the residue, after treatment with ether is titrated with a very small quantity of water, and the liquid portion separated with a filter pump. Benzoyl-ecognine remains behind, while the much more soluble ecognine is dissolved out. If care is taken, the yield of benzoyl-ecognine amounts to eighty percent of the weight of the original ecognine. From the mother liquids some more benzoyl-ecognine may be obtained by evaporation. And all the unconverted ecognine is recovered and added to the next operation.
Benzoyl-ecognine thus obtained was found to absolutely identical with that previously known as a decomposition product.
The conversion of benzoyl-ecognine into cocaine had already been accomplished or at least pointed out some time ago by Einhorn. In 1885 W. Merck found that by heating benzoyl-ecognine with iodide of methyl and methylic alcohol in sealed tubes the former was partly converted into cocaine. But the yield was only about 4% of the amount of benzoyl-ecognine employed. Einhorn subsequently discovered a much more simple and efficient method for converting benzoyl-ecognine into ethylic or other compound ethers.
Cocaine is chemically benzoyl-ecognine-methylic ester. The method which Einhorn used to produce the ethylic ester was as follows:
Make a solution of benzoyl-ecognine in ethylic alcohol and pass dry hydrochloric acid gas into it, which will cause a considerable rise in temperature for some time. Keep on passing the gas until the liquid has become cold. Then boil it for one hour under an upright condenser and afterwards evaporate it on a water bath. Dissolve the residue in water and precipitate the filtered solution with soda. The precipitate in this case was a base which differed from natural cocaine by containing the ethyl nucleus C2H3 instead of that of Methyl CH3 which exists in true cocaine. In order to obtain the latter it is only necessary ( at least this is implied by the statements of Lieberman an d Giesel) to substitute pure methylic alcohol for the ethylic, to pass dry hydrochloric gas through the solution, and to proceed further as described. By this method an extremely pure cocaine is obtained which forms magnificent crystals. This synthetic cocaine has been tested for its physiological effects by Prof. O. Liebreich and ascertained by him to be identical with that directly obtained from coca.”
The proportion of alkaloids contained in Coca leaves is influenced by the method of the growth of the plant, and the yield is dependent upon the manner of curing the leaves and their preservation. The percentage ranges from a mere trace to about one per cent. Bignon considers that well preserved leaves will yield fully as much as recent leaves, varying from nine to eleven grammes of the mixed alkaloids per kilogram, the latter being more than one per cent. Niemann obtained from his original process 0.25 per cent, of cocaine, while the present yield is more than double that. From a number of assays made during the last few years in the laboratory of an American manufacturer the following percentages of alkaloid were obtained: 0.53, 0.51, 0.63, 0.63, 0.57, 0.60, 0.66, 0.55, 0.70, 0.70, 0.65, 0.67, 0.54, 0.70, 0.32, 0.42, 0.52, 0.85, 0.48, 1.3, 0.78, 0.70, 0.40, 0.63. This will serve as an index of the quantity of total alkaloid commonly found in the average leaf of good quality as it reaches North America.
In determining the amount of alkaloids present in a given specimen of Coca, it is essential that the selected leaves be finely powdered, and mixed with a suitable menstruum that will not cause undue annoyance from gummy and resinous matters while setting free the essential constituents. These are washed out of the solution by an appropriate solvent, dried and weighed, or estimated by using some reagent the equivalent values of which have been determined by experiment. Various alkalies, as lime, soda or magnesia, have been suggested for admixture with the leaves for the purpose of liberating the alkaloids, which are transformed to soluble salts by acidulated water and washed out with strong alcohol. The details of the production of the Coca alkaloids commercially are kept as a trade secret, but the broad methods of manufacture are all similar, as several will illustrate.
Dr. Squibb has suggested the following process for the preparation of cocaine on a small scale: One hundred grammes of finely ground leaves are moistened with 100 c.c. of 7 percent solution of sodium carbonate, packed in a percolator, and sufficient kerosene added to make 700 c.c. of percolate. This is transferred to a separator, and 30 c.c. of 2 percent solution of hydrochloric acid added and shaken. After separation the watery solution is drawn off from below into a smaller separator, and this process is repeated three times, the alkaloid being in the smaller separator as an acid hydrochlorate. This is precipitated in ether with sodium carbonate, and evaporated at low heat with constant stirring and the product weighed.
Another process is to digest Coca leaves in a closed vessel at 700 C. for two hours with a very weak solution of caustic soda, and petroleum boiling between 2000 to 250°. The mass is filtered, pressed while tepid, and the filtrate allowed to stand until the petroleum separates from the aqueous liquid. The former is then drawn off and neutralized with weak hydrochloric acid. The bulky precipitate of cocaine hydrochloride being recovered from the aqueous liquid by evaporation.
Gunn made a series of tests to determine what relation the methods of extraction had to the alkaloidal yield, and concluded that the modified method of Lyons obtained the most alkaloids. This is substantially as follows: Shake 10 grammes of finely powdered leaves with 95 c.c. of petroleum benzin and add 5 c.c. of the following mixture: Absolute alcohol, 19 volumes; concentrated solution ammonia, 1 volume. Again shake for a few minutes, and set aside for twenty-four hours with occasional shaking. Decant rapidly 50 C.C. of the clear fluid, or, if it is not clear, filter it, washing the filter with benzin. Transfer to a separator containing 5 C.C. of water, to which has been added 6 to 8 drops of dilute sulphuric acid (1 to 5 by weight). Shake vigorously; when the fluids have separated draw the aqueous portion into a one ounce vial. Wash the contents of the separator with 2 c.c. of acidulated water (1 drop of the dilute acid). Shake, draw off into the vial, and continue this two or three times, until a drop tested on a mirror with Mayer’s reagent shows only faint turbidity. Add to the aqueous fluid 15 c.c. of benzin, shake, and when separation is complete, pour off the benzin. Add to the vial 15 c.c. of stronger ether, U. S. P., with sufficient ammonia to render the mixture decidedly alkaline. Shake, and when separation is complete, decant the ether carefully into a capsule. Wash the residue in the vial with two or three successive portions of fresh ether until the aqueous fluid is free from alkaloid, as shown by the test. Evaporate the ether over a water bath. Dry the alkaloid to constant weight, weigh, multiply the result expressed in decigrammes by two, which will present the percentage of crude cocaine.
Instead of extracting the alkaloid from the acid aqueous solution a simple method adapted to use in the field may be followed, in which the alkaloid is estimated by titration with Mayer’s reagent. An acid solution representing 5 grammes of the leaves should be made up to a volume of 15 c.c, and the reagent added as long as it continues to precipitate in the clear filtrate. In this way, with half strength solution, 3.5 c.c reagent represents 0.2 per cent, of alkaloid.
Mayer’s reagent, or the decinormal mercuric potassium iodide of the U. S. P., is prepared as follows: Mercuric chloride, 13.546 grammes, dissolved in 600 c.c. of water; potassium iodide, 49.8 grammes, dissolved in 190 c.c. of water; mix the two solutions and add sufficient water to make the whole measure, at 590 F., exactly 1000 c.c.
When Mayer’s reagent is added drop by drop to an acid solution containing cocaine (1:200 to 1:600) there is at first produced a heavy white precipitate, which collects at once into curdy masses; a drop of solution should be examined on a mirror, and should not show more than slight turbidity when determining the final traces. Dr. Lyons suggests that after adding a certain quantity of the reagent it will be found that the filtered fluid which still gives a heavy precipitate with Mayer’s reagent produces a precipitate also in a fresh solution of cocaine. It is thus evident that the precipitation is complete only when an excess of reagent is present in the fluid; and it is found advisable to correct the reading from the burette by subtracting for each c.c. of fluid present at the end of the titration 0.085 c.c. (if the half strength reagent is used); the remainder multiplied by ten will give the quantity of alkaloid indicated in milligrammes. The best method of following the process is to throw the fluid on a filter after each addition of reagent. Solutions of the alkaloid 1 :400 appear to yield better results than solutions stronger or weaker than this.
One c.c. of Mayer’s reagent will precipitate about 7.5 milligrammes of the mixed alkaloids from solutions in which alcohol is not present. As a rule the quantity of alkaloidal precipitate by this reagent is greater than the quantity of cocaine that can be extracted by washing out the alkaline solution with ether, so that in exact examinations a recourse to weighing is considered advisable. The dried precipitate weighed and multiplied by 0.406 will give about the amount of alkaloid present. With Mayer’s reagent used in half strength the following values for the equivalent of the reagent are given:
The following table may also be of service:
Results higher or lower than those indicated are beyond the limits of the experiment and would call for repetition.
The principal tests employed to determine the purity of cocaine hydrochloride are the permanganate of potash and Maclagan’s ammonia test. When one drop of a one percent solution of permanganate of potash is added to 5 c.c. of a two percent solution of hydrochloride of cocaine mixed with three drops of dilute sulphuric acid, it occasions a pink tint which should not entirely disappear within half an hour. When added to a stronger solution it occasions a precipitate of rhombic plates, which decompose on heating. If cinnamyl-cocaine be present the odor of bitter almonds is given off with the decomposition.
The Maclagan test is based upon the supposition that the amorphous alkaloids of Coca when set free by ammonia are separated as oily drops and so form a milky solution. It is employed by adding one or two drops of ammonia to a solution of cocaine, which is then vigorously stirred with a glass rod. If the salt is pure a formation of crystals will be deposited upon the rod and upon the side of the vessel within five minutes, while the solution will remain clear. If isatropyl-cocaine be present crystallization will not take place and the solution will become milky.
Considerable stress has been laid upon the value of this test for determining the purity of cocaine salts. Dr. Guenther asserts that a perfectly pure cocaine will not show the Maclagan reaction, while if a small quantity of a new base which he described as cocathylin, with a melting point of 1100 C, be present, the test will be pronounced. In endeavoring to show that this was an error, one of the largest manufacturers of cocaine in Germany worked up four thousand kilos of Coca leaves, and though they failed to find the new base which had been mentioned, they also proved that a pure cocaine will respond positively to the Maclagan test. In support of this Paul and Cowley have expressed the opinion that any cocaine which does not satisfy this test should not be regarded as sufficiently pure for pharmaceutical purposes, views which are also maintained by E. Merck.
Of the various reagents that have been found delicate in testing for cocaine Mayer’s reagent will detect one part in one hundred thousand, while a solution of iodine in iodide of potash will determine one part in four hundred thousand, with a very faint yellow precipitate.
It has been shown by Gerrard that mydriatic alkaloids have a peculiar action with mercuric chloride, from the aqueous solution of which they precipitate mercuric oxide, the other natural alkaloids giving no precipitate at all, or at least not separating mercuric oxide. The late Professor Flückiger, verifying this action on cocaine, found the test recorded a very abundant purely white precipitate, which very speedily turned red, as in the case of the other mydriatic alkaloids.
It has been found, on treating cocaine or one of its salts in the solid state with fuming nitric acid, sp. gr. 1.4, evaporating to dryness and treating with one or two drops of strong alcoholic solution of potash, there is given off on stirring this with a glass rod a distinct odor suggestive of peppermint. This odor test has been pronounced very delicate and is distinctive for cocaine, no other alkaloid having been found to yield a similar reaction.
There are several cocaine manufacturers in Peru. A few years ago there were five in Huanuco, one in the District of Mozon, one in Pozuso, two at Lima, one at Callao, at least two of which are run on an extensive scale. In 1894 the amount of the crude product manufactured in Peru and sent abroad for purification was four thousand seven hundred and sixteen kilos. A personal communication from Peru, dated January 15, 1900, states that the local manufacturers of cocaine are increasing their facilities and claim that they work with a better method than is followed elsewhere.
In 1890 Dr. Squibb called attention to the fact that crude cocaine was made so efficiently in Peru that it seemed highly probable that the importation of Coca leaves to this market was nearly at an end. This crude cocaine has a characteristic nicotine odor; it comes in a granular powder or in fragments of press cake, generally of a dull creamy white color, but rarely quite uniform throughout, the color ranging from dirty brownish white to very nearly white. Some of the fragments are horny, compact and hard, while others are softer and more porous. The following process has been given for determining the amount of cocaine present in the crude product:
A small quantity being taken from a large number of lumps in the parcels, selected on account of their difference in appearance, the determination of moisture in the samples so selected is found by fusion at 910 C. The solubility of the samples in ether at a specific gravity .725 at 15.60 C, is then tested. The insoluble residue is thoroughly washed with ether, dried and weighed. The alkaloid dissolved by the ether is converted into oxalate, and the oxalate shaken out by water. The residue which is soluble in ether is then determined by evaporation of the ethereal solution. The aqueous solution of cocaine oxalate is rendered faintly alkaline by soda; the freed alkaloid shaken out with ether, and after spontaneous evaporation of the ether and complete drying of the crystals produced, the pure alkaloid is estimated. The usual yield of pure crystallizable alkaloid from this crude product varies from fifty to seventy-five percent.
Crude cocaine when united with acids assumes an intense green color, due to the presence of benzoyl-ecgonine, while its characteristic chemical reaction is its property of splitting into benzoic acid and methyl alcohol. Cocaine combines readily with acids to form salts, which are readily soluble in water and alcohol, though insoluble in ether. These salts, owing to their more ready solubility, have a more marked anӕsthetic action on mucous surfaces than the pure alkaloid. There has been prepared benzoate, borate, citrate, hydrobromate, hydrochlorate, nitrate, oleate, oxalate, salicylate, sulphate, tartrate, etc.
According to the U. S. Pharmacopaia the following are the characteristics of cocaine hydrochlorate, the salt commonly employed: “Colorless, transparent crystals, or a white crystalline powder, without odor, of a saline, slightly bitter taste, and producing upon the tongue a tingling sensation, followed by numbness of some minutes’ duration. Permanent in the air. Soluble at W C. (59o F.) in 0.48 part of water and in 3.5 parts of alcohol; very soluble in boiling water and in boiling alcohol; also soluble in 2,800 parts of ether or in 17 parts of chloroform. On heating a small quantity of the powdered salt for twenty minutes at a temperature of 100° C. (212° F.), it should not suffer any material loss (absence of water of crystallization). The prolonged application of heat to the salt or to its solution induces decomposition. At 193° C. (379.4° F.) the salt melts with partial sublimation, forming a light brownish yellow liquid. When ignited it is consumed without leaving a residue. The salt is neutral to litmus paper.
In reviewing the research of many workers it may be seen how each has closely approached, often with a mere hint or suggestion, results which later have been verified and described more in detail. Through this repetition many new facts have been made positive to us. Assertions have been strengthened or have been cast aside, and while the result has been to render a cocaine of purer quality, it has at the same time emphasized the immensity of our ignorance concerning the subtleties of alkaloidal formation. More than all, these researches must impress the fact that similar changes to those which are possible in the laboratory of the chemist are also at work in Nature’s laboratory, and that the therapeutic influence and efficiency of Coca, as of any remedy taken into the body, must be markedly affected by the transmutations of the organism.” (End of Chapter)
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“Erythroxylon Coca: A Treatise On Brain Exhaustion”, Dr. William Tibbles, 1877
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“Coca – Its Therapeutic Applications”, Angelo Mariani, 1890
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