Alkaloids cocaine

The coca bush Erythroxylon coca, native to upland rain forest areas of Colombia, Ecuador, Peru, Bolivia, and western Brazil, is the source of the alkaloid cocaine. 

The answer is b. (Kn.lzu.ng, p 5.38.) Crack is the free-base (nonsalt) form of the alkaloid cocaine. It is called crack because, when heated, it makes a crackling sound. Heating crack enables a person to smoke it the drug is readily absorbed through the lungs and produces an intense euphoric effect in seconds Use has led to seizures and cardiac arrhythmias. Some of cocaine s effects (sympathomimetic) are due to blockade of norepinephrine reuptake into presynaptic terminals it does not block receptors. Flashbacks can occur with use of LSD and mescaline but have not been associated with the use of cocaine. 

The coca leaf is either consumed by the natives of South America or exported to other countries for consumption. Another use of the coca leaf is in the extraction of cocaine either for illegitimate or legitimate use. The majority of the legal and/or clandestine cocaine factories are in South America due to the cost and bulk of transporting the whole leaf. In 1961, Bolivia produced an annual crop of from 12,000 to 18,000 tons of leaves although only half reached the legal market. The alkaloid cocaine is extracted from the coca leaf in basically three different chemical procedures. These procedures are used both in licit and illicit labs in the production of cocaine. 

When we look at another tropane alkaloid, cocaine, we get a different scenario. Cocaine is obtained from the coca plant Erythroxylum coca, and is a powerfnl local anaesthetic, bnt now known primarily as a dmg of abuse. There is no chiral centre in the acid portion, which is benzoic acid, but the optical activity of cocaine comes from the alcohol methylecgonine. Because of the ester function in methylecgonine, the tropane system is no longer symmetrical, and the four chiral centres all contribute towards optical activity. 

This holds true especially for the alkaloid cocaine from Erythroxylon coca. Cocain has various mechanisms of action it is a local anaesthetic and an indirect, central acting sympathomimetic. It increases the effects of released or externally applied catecholamines but reduce the effect of other indirect sympathomimetic drugs. 

The natural alkaloid cocaine was introduced as the first local anesthetic drug in clinical surgery... 

Synaptic dopamine transporters are inhibited by various psychotropic alkaloids including the tropane alkaloid cocaine [189, 190], the indole alkaloid ibogaine [191] and by amphetamine (methylphenethylamine) and related compounds [192, 193]. 

Synaptic serotonin (5-hydroxytryptamine) transporters are inhibited by amphetamines, the tropane alkaloids cocaine and ecgonine [194] and by the indole alkaloid ibogaine (12-methoxyibogamine) and its demethylation product ibogamine [191, 195]. Hyperforin is a major antidepressant constituent of St. John s Wort (Hypericum perforatum) and inhibits serotonin uptake by elevating cytosolic Na+ [196]. The additional... 

Alkaloids Cocaine, morphine Separated on a C-18 high carbon loaded (20%) silica column mobile phase water (buffered with 0.02 M KH2P04, pH 3)—acetonitrile (75 25) detected by UV at 254 nm... 

Toxicants may have three effects on pulse rate bradycardia (decreased rate), tachycardia (increased rate), and arrhythmia (irregular pulse). Alcohols may cause either bradycardia or tachycardia. Amphetamines, belladonna alkaloids, cocaine, and tricyclic antidepressants (see imi-primine hydrochloride in Figure 6.12) may cause either tachycardia or arrhythmia. Toxic doses of digitalis may result in bradycardia or arrhythmia. The pulse rate is decreased by toxic exposure to carbamates, organophosphates, local anesthetics, barbiturates, clonidine, muscaric mushroom toxins, and opiates. In addition to the substances mentioned above, those that cause arrhythmia are arsenic, caffeine, belladonna alkaloids, phenothizine, theophylline, and some kinds of solvents. 

Hunter JG, Loy HC, Markovitz L, Kim US. Spontaneous pneumomediastinum following inhalation of alkaloidal cocaine and emesis case report and review. Mt Sinai J Med 1986 53(6) 491-3. 

Anatoxin-a, the first highly potent cyanotoxin to have its structure and absolute stereochemistry elucidated, was originally isolated from a unialgal clone of Anabaena Jlos-aquae (NRC-44h) [5]. The structure was confirmed by X-ray crystallographic data for the N-acetyl derivative [11] and additional studies have since provided further proof for the structure and stereochemistry (for example, [12]). Anatoxin-a is an unsymmetrical bicyclic secondary amine, and was the first naturally occurring alkaloid discovered to contain a 9-azabicyclo[4,2,l]nonane (homotropane) skeleton. Homotropanes are one-carbon analogs of the tropanes and, as such, are structurally closely related to the well-known alkaloid cocaine. 

The natives of Peril were learning to ease their physical pains by chewing the leaves of coca shrub (Erytbroxylon tmxillence, "Rushy), which contain, among others, the alkaloid cocaine (11), and European citizens were recognizing other poisons such as coniine (12), from die poison hemlock ( Comum maculatum... 

Which of the two is the cis form and which the trans form has not been determined. A third cinnamic acid, viz., iso-cinnamic acid, is also known, but the constitution of it has not been established. Cinnamic acid is found in nature in the resin storax both as the free acid and as the cinnamic alcohol ester, styrin. It is also found in Peru and Tolu balsams as the free acid and as the benzyl alcohol ester, the benzoic acid ester of benzyl alcohol being present also. Thus benzyl alcohol, benzoic acid, cinnamic alcohol and cinnamic acid are all constituents of esters present in these plant resins. Allo-cinnamic acid, the geometric isomer, is obtained from coca leaves from which the alkaloid cocaine is also obtained (p. 896). When cinnamic acid is heated with lime it loses carbon dioxide and yields the unsaturated side-chain hydrocarbon st3rrene, or phenyl ethylene, CeHs—CH = CH2. On reduction it yields first cinnamic aldehyde, found in oil of cinnamon (p. 842) and then cinnamic alcohol. Both cinnamic acid and allo-cinnamic acid yield anhydrides. 

Belonging to the same chemical group as atropine is the important alkaloid cocaine, C17H21O4N. It is obtained from the leaves of the coca plant, Erythroxylon coca, which grows in South America (Bolivia and Peru) and in Java and Ceylon. Distinction should be made between the coca plant and the cacao bean from which cocoa and chocolate are made. 

Putrescine A-methyltransferase (PMT, EC 2.1.1.53) catalyses the first specific step in the biosynthesis of tropane alkaloids, cocaine and nicotine [123]. Putrescine is methylated by PMT via SAM (S-adenosylmethionine) transferring the methyl group from SAM to an amino group of putrescine. Fig. (1). This enzyme has been isolated from roots of both Nicotiana tabacum and D. stramonium [124], and the activity of this enzyme is restricted to the roots of Solanaceous species corroborated by results describing a root pericycle-specific activity in A. belladonna [125]. Nevertheless, more recently, a low mRNA pmt transcript level in leaves of N. tabacum, with a rise in transcript level after mechanical wounding has been detected [126]. 

The alkaloid cocaine was discovered in coca leaves in 1860 (1). It had long been known that the South American Indians were in the habit of chewing these leaves as a stimulant to enable them to stand great exertion without fatigue. The first use of cocaine in this country was for a similar purpose, but its great importance among alkaloids at the present time is due chiefly to Roller s important discovery that cocaine is a powerful and rapid local anesthetic. 

Q,C,opium alkaloids,cocaine, caffeine Separation by means of dynamic coating HPLC Corasil I and II, dynamically coated with Poly G-300 (2%) 1000x1 Heptane-EtOH(lOtl) with different percentage of 1,2 saturation with the stationary phase Poly G-300... 

This tactic was used successfully with the alkaloid cocaine (Fig. 7.21). It was well known that cocaine had local anaesthetic properties and it was hoped to develop a local anaesthetic based on a simplified structure of cocaine which could be easily synthesized in the laboratory. Success resulted with the discovery of procaine (or Novocaine) in 1909. 

The most important ingredient of coca leaves is the alkaloid cocaine, which has local... 

Cocaine and morphine are two very well known alkaloids. Cocaine is a compound extracted from the leaves of the coca plant. Long term usage of cocaine causes addiction and harms the central nervous system. 

Large-scale production of cocaine (both licit and illicit) essentially involves extraction of the total bases, which are then totally hydrolyzed so that all three ester alkaloids, cocaine, cinnamoyl cocaine, and the truxillines, are converted to ecgonine. The ecgonine is then methylated, followed by esterification with benzoic acid to cocaine. All of the ecgonine in the leaves is converted to the desired product in this way, which is a more efficient process than attempting to extract and separate out only the actual cocaine content from the plant. 

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