Alkaloids are a class of basic, naturally occurring organic compounds that contain at least one nitrogen atom. This group also includes some related compounds with neutral and even weakly acidic properties. Some synthetic compounds of similar structure may also be termed alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen or sulfur. More rarely still, they may contain elements such as phosphorus, chlorine, and bromine.
Cocaine is a tropane alkaloid that acts as a central nervous system (CNS) stimulant. As an extract, it is mainly used recreationally, and often illegally for its euphoric and rewarding effects. It is also used in medicine by Indigenous South Americans for various purposes and rarely, but more formally, as a local anaesthetic or diagnostic tool by medical practitioners in more developed countries. It is primarily obtained from the leaves of two Coca species native to South America: Erythroxylum coca and E. novogranatense. After extraction from the plant, and further processing into cocaine hydrochloride, the drug is administered by being either snorted, applied topically to the mouth, or dissolved and injected into a vein. It can also then be turned into free base form, in which it can be heated until sublimated and then the vapours can be inhaled.
Coca is any of the four cultivated plants in the family Erythroxylaceae, native to western South America. Coca is known worldwide for its psychoactive alkaloid, cocaine.
Methylecgonine cinnamate is a natural tropane alkaloid found within the coca plant. Its more common name, cinnamoylcocaine, reflects its close structural similarity to cocaine. It is pharmacologically inactive, but some studies funded by anti-drug agencies imply that it is active when smoked. Furthermore, the discovery of differing impurity products yielding methylecgonine cinnamate in confiscated cocaine have led enforcing agencies to postulate that illicit manufacturers have changed their oxidation procedures when refining cocaine from a crude form. Methylecgonine cinnamate can dimerize to the truxillic acid derivative truxilline. It is notable that methylecgonine cinnamate is given in patents of active cocaine analogue structures.
Benzoylecgonine is the main metabolite of cocaine, formed by the liver and excreted in the urine. It is the compound tested for in most cocaine urine drug screens and in wastewater screenings for cocaine use.
Phytochemistry is the study of phytochemicals, which are chemicals derived from plants. Phytochemists strive to describe the structures of the large number of secondary metabolites found in plants, the functions of these compounds in human and plant biology, and the biosynthesis of these compounds. Plants synthesize phytochemicals for many reasons, including to protect themselves against insect attacks and plant diseases. The compounds found in plants are of many kinds, but most can be grouped into four major biosynthetic classes: alkaloids, phenylpropanoids, polyketides, and terpenoids.
Tropinone is an alkaloid, famously synthesised in 1917 by Robert Robinson as a synthetic precursor to atropine, a scarce commodity during World War I. Tropinone and the alkaloids cocaine and atropine all share the same tropane core structure. Its corresponding conjugate acid at pH 7.3 major species is known as tropiniumone.
Tropane is a nitrogenous bicyclic organic compound. It is mainly known for the other alkaloids derived from it, which include atropine and cocaine, among others. Tropane alkaloids occur in plants of the families Erythroxylaceae and Solanaceae.
Hygrine is a pyrrolidine alkaloid, found mainly in coca leaves (0.2%). It was first isolated by Carl Liebermann in 1889 as an alkaloid accompanying cocaine in coca. Hygrine is extracted as a thick yellow oil, having a pungent taste and odor.
Ecgonine is a tropane alkaloid found naturally in coca leaves. It has a close structural relation to cocaine: it is both a metabolite and a precursor, and as such, it is a controlled substance in many jurisdictions, as are some substances which can be used as precursors to ecgonine itself.
Coca tea, also called mate de coca, is a herbal tea (infusion) made using the raw or dried leaves of the coca plant, which is native to South America. It is made either by submerging the coca leaf or dipping a tea bag in hot water. The tea is most commonly consumed in the Andes mountain range, particularly Argentina, Bolivia, Colombia, Ecuador and especially in Peru, where it is consumed all around the country. It is greenish yellow in color and has a mild bitter flavor similar to green tea with a more organic sweetness.
Cocaine is a naturally occurring organic compound, an alkaloid, present in the leaves of the coca plant.
Free base is a descriptor for the neutral form of an amine commonly used in reference to illicit drugs. The amine is often an alkaloid, such as nicotine, cocaine, morphine, and ephedrine, or derivatives thereof. Freebasing is a more efficient method of self-administering alkaloids via the smoking route.
Allopumiliotoxins are a structural division in the pumiliotoxin-A class of alkaloids. The compounds of the pumiliotoxin-A class are primarily found in the skins of frogs, toads, and other amphibians and are used as a chemical defense mechanism to ward off predators, microorganisms, and ectoparasites. The compounds were originally discovered in neotropical dendrobatid frogs, but are also found in the mantellid frogs of Madagascar, myobatrachid frogs of Australia, and bufonid toad of South America. Frogs possessing this defense mechanism have aposematic coloring.
Tropane alkaloids are a class of bicyclic [3.2.1] alkaloids and secondary metabolites that contain a tropane ring in their chemical structure. Tropane alkaloids occur naturally in many members of the plant family Solanaceae. Certain tropane alkaloids such as cocaine and scopolamine are notorious for their psychoactive effects, related usage and cultural associations. Particular tropane alkaloids such as these have pharmacological properties and can act as anticholinergics or stimulants.
A loline alkaloid is a member of the 1-aminopyrrolizidines, which are bioactive natural products with several distinct biological and chemical features. The lolines are insecticidal and insect-deterrent compounds that are produced in grasses infected by endophytic fungal symbionts of the genus Epichloë. Lolines increase resistance of endophyte-infected grasses to insect herbivores, and may also protect the infected plants from environmental stresses such as drought and spatial competition. They are alkaloids, organic compounds containing basic nitrogen atoms. The basic chemical structure of the lolines comprises a saturated pyrrolizidine ring, a primary amine at the C-1 carbon, and an internal ether bridge—a hallmark feature of the lolines, which is uncommon in organic compounds—joining two distant ring carbons. Different substituents at the C-1 amine, such as methyl, formyl, and acetyl groups, yield loline species that have variable bioactivity against insects. Besides endophyte–grass symbionts, loline alkaloids have also been identified in some other plant species; namely, Adenocarpus species and Argyreia mollis.
The biosynthesis of cocaine has long attracted the attention of biochemists and organic chemists. This interest is partly motivated by the strong physiological effects of cocaine, but a further incentive was the unusual bicyclic structure of the molecule. The biosynthesis can be viewed as occurring in two phases, one phase leading to the N-methylpyrrolinium ring, which is preserved in the final product. The second phase incorporates a C4 unit with formation of the bicyclic tropane core.
Coca alkaloids are the alkaloids found in the coca plant, Erythroxylum coca. They are predominantly of either the pyrrolidine or the tropane types.
The Kröhnke pyridine synthesis is reaction in organic synthesis between α-pyridinium methyl ketone salts and α, β-unsaturated carbonyl compounds used to generate highly functionalized pyridines. Pyridines occur widely in natural and synthetic products, so there is wide interest in routes for their synthesis. The method is named after Fritz Kröhnke.
Methylecgonine, also known as ecgonine methylester is a prominent tropane alkaloid found in coca leaves. It is metabolite of cocaine, and may be used as a precursor for it. It also occurs as minor alkaloid in roots of many Datura species such as Datura stramonium and Datura innoxia.
