Кокаїн

НАТУРАЛЬНІ Й СИНТЕТИЧНІ, ПОПУЛЯРНІ Й НЕЗВИЧНІтропановий алкалоїд · листя коки

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Верхні нотиПіраміда
—Сила
—Стійкість
—Походження
Зразок
Кокаїн як парфумерна сировина
Верхні ноти
Erythroxylum coca
Визначення

Cocaine is a tropane alkaloid and central nervous system stimulant, derived primarily from the leaves of two coca species native to South America. Cocaine hydrochloride is described as odorless, but it hydrolyzes in moist air to give methyl benzoate, which has a pleasant odor.

БЕЗ ЗАПАХУ
Benzoylmethylecgonine, methyl benzoylecgonine, l-cocaine, cocainum, coke
Type
Акорд
Olfactive family
Ароматичні
Source
Leaves of Erythroxylum coca and E. novogranatense
Chemical class
Tropane alkaloid
Інструменти
Піраміда
ВВерхні ноти
СНоти серця
ББазові ноти

Запах

Cocaine hydrochloride is described as odorless. Fresh samples of the dried coca leaves have a strong tea-like aroma. Methyl benzoate, which cocaine hydrochloride yields by hydrolysis in moist air, has a pleasant odor and a fruity aroma.

Докладно

Chemistry

Cocaine is an ester of benzoic acid and a nitrogen-containing base. As a tropane alkaloid, cocaine is a weak base and readily forms salts when combined with acids. The most commonly encountered form is the hydrochloride salt, although other salts such as the sulfate and nitrate are occasionally observed. The freebase is practically insoluble in water, whereas the hydrochloride salt is water-soluble.

Methyl benzoate

Cocaine hydrochloride hydrolyzes in moist air to give methyl benzoate. Methyl benzoate is the methyl ester of benzoic acid. It is a colorless liquid that is poorly soluble in water but miscible with organic solvents. It is formed by the condensation of methanol and benzoic acid. In nature it occurs in ylang-ylang, tuberose and Michelia. It can also be isolated from the freshwater fern Salvinia molesta. It is one of many compounds that attract males of various species of orchid bees.

The coca plant

The coca plant resembles a blackthorn bush and grows to a height of 2 to 3 m. Fresh samples of the dried leaves are deep green on the upper surface and grey-green on the lower surface. Erythroxylum coca is one of the two species of cultivated coca. The cocaine alkaloid content in dry leaves of Erythroxylum coca var. coca ranges from 0.23% to 0.96%. Coca alkaloids are predominantly of either the pyrrolidine or the tropane type. Among the tropane-type coca alkaloids are benzoylecgonine, cocaine, ecgonidine and ecgonine.

Legal status

Cocaine is listed as a Schedule I drug in the United Nations 1961 Single Convention on Narcotic Drugs. The coca leaf is also placed in Schedule I of that Convention, together with cocaine and heroin. Cultivation, sale and possession of unprocessed coca leaf, but not of any processed form of cocaine, is generally legal in countries such as Bolivia, Peru, Chile and the Argentine Northwest, where traditional use is established.

Traditional and historical use

Chewing coca leaves dates back at least 8,000 years in South America, as evidenced by coca leaves and calcite found in house floors in Peru's Nanchoc Valley. The consumption of coca tea is common among all sectors of society in the Andean countries. Coca leaf is sold packaged into teabags in most grocery stores in the region. A cola maker used coca leaf extract in its products from 1885 until about 1903, when it switched to a decocainized leaf extract.

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Отримання й хімія

Спосіб отримання

The leaves are processed into cocaine paste, a crude mixture of coca alkaloids, from which cocaine base is isolated and then converted to cocaine hydrochloride. Extracting cocaine from coca requires several solvents and a chemical process known as an acid-base extraction, which can efficiently isolate the alkaloids from the plant material. Pure cocaine is prepared by neutralizing its compounding salt with an alkaline solution, which precipitates non-polar basic cocaine.

Формула
C₁₇H₂₁NO₄
CAS
50-36-2
Ботанічна назва
Erythroxylum coca
Зовнішній вигляд
Colorless to white crystals or white powder; freebase: colorless, transparent, crystalline substance; crack: off-white, jagged-edged rocks
Синоніми
Benzoylmethylecgonine, methyl benzoylecgonine, l-cocaine, cocainum, coke
Статус IFRA
Див. примітку

No IFRA Standard for the material itself (51st Amendment)

Фізичні властивості
Температура кипіння
187 °C at 0.1 mm Hg
Температура плавлення
98 °C; hydrochloride about 195 °C, or about 197 °C with decomposition

У парфумерії

Methyl benzoate, which forms when cocaine hydrochloride hydrolyzes in moist air, has perfumery among its uses. Coca is used industrially in the cosmetics and food industries. A decocainized extract of coca leaf is one of the flavoring ingredients in a cola drink.

Роль у формулі
01немає (без запаху)
Форми випуску
гідрохлорид вільна основа крек паста коки

Див. також

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