alkaloid

alkaloid, any of a class of naturally occurring organic nitrogen-containing bases. Alkaloids have diverse and important physiological effects on humans and other animals. Well-known alkaloids include morphine, strychnine, quinine, ephedrine, and nicotine.

Alkaloids are found primarily in plants and are especially common in certain families of flowering plants. In fact, as many as one-quarter of higher plants are estimated to contain alkaloids, of which several thousand different types have been identified. In general, a given species contains only a few kinds of alkaloids, though both the opium poppy (Papaver somniferum) and the ergot fungus (Claviceps) each contain about 30 different types. Certain plant families are particularly rich in alkaloids; all plants of the poppy family (Papaveraceae) are thought to contain them, for example. The Ranunculaceae (buttercups), Solanaceae (nightshades), and Amaryllidaceae (amaryllis) are other prominent alkaloid-containing families. A few alkaloids have been found in animal species, such as the New World beaver (Castor canadensis) and poison-dart frogs (Phyllobates). Ergot and a few other fungi also produce them.

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opium: Opium alkaloids

The function of alkaloids in plants is not yet understood. It has been suggested that they are simply waste products of plants’ metabolic processes, but evidence suggests that they may serve specific biological functions. In some plants, the concentration of alkaloids increases just prior to seed formation and then drops off when the seed is ripe, suggesting that alkaloids may play a role in this process. Alkaloids may also protect some plants from destruction by certain insect species.

The chemical structures of alkaloids are extremely variable. Generally, an alkaloid contains at least one nitrogen atom in an amine-type structure—i.e., one derived from ammonia by replacing hydrogen atoms with hydrogen-carbon groups called hydrocarbons. This or another nitrogen atom can be active as a base in acid-base reactions. The name alkaloid (“alkali-like”) was originally applied to the substances because, like the inorganic alkalis, they react with acids to form salts. Most alkaloids have one or more of their nitrogen atoms as part of a ring of atoms, frequently called a cyclic system. Alkaloid names generally end in the suffix -ine, a reference to their chemical classification as amines. In their pure form most alkaloids are colourless, nonvolatile, crystalline solids. They also tend to have a bitter taste.

Interest in the alkaloids stems from the wide variety of physiological effects (both wanted and unwanted) they produce in humans and other animals. Their use dates back to ancient civilizations, but scientific study of the chemicals had to await the growth of organic chemistry, for not until simple organic bases were understood could the intricate structure of the alkaloids be unraveled. The first alkaloid to be isolated and crystallized was the potent active constituent of the opium poppy, morphine, in about 1804.

Alkaloids are often classified on the basis of their chemical structure. For example, those alkaloids that contain a ring system called indole are known as indole alkaloids. On this basis, the principal classes of alkaloids are the pyrrolidines, pyridines, tropanes, pyrrolizidines, isoquinolines, indoles, quinolines, and the terpenoids and steroids. Alternatively, alkaloids can be classified according to the biological system in which they occur. For example, the opium alkaloids occur in the opium poppy (Papaver somniferum). This dual classification system actually produces little confusion because there is a rough correlation between the chemical types of alkaloids and their biological distribution.

The medicinal properties of alkaloids are quite diverse. Morphine is a powerful narcotic used for the relief of pain, though its addictive properties limit its usefulness. Codeine, the methyl ether derivative of morphine found in the opium poppy, is an excellent analgesic that is relatively nonaddictive. Certain alkaloids act as cardiac or respiratory stimulants. Quinidine, which is obtained from plants of the genus Cinchona, is used to treat arrhythmias, or irregular rhythms of the heartbeat. Many alkaloids affect respiration, but in a complicated manner such that severe respiratory depression may follow stimulation. The drug lobeline (from Lobelia inflata) is safer in this respect and is therefore clinically useful. Ergonovine (from the fungus Claviceps purpurea) and ephedrine (from Ephedra species) act as blood-vessel constrictors. Ergonovine is used to reduce uterine hemorrhage after childbirth, and ephedrine is used to relieve the discomfort of common colds, sinusitis, hay fever, and bronchial asthma.

Many alkaloids possess local anesthetic properties, though clinically they are seldom used for this purpose. Cocaine (from Erythroxylum coca) is a very potent local anesthetic. Quinine (from Cinchona species) is a powerful antimalarial agent that was formerly the drug of choice for treating that disease, though it has been largely replaced by less toxic and more effective synthetic drugs. The alkaloid tubocurarine is the active ingredient in the South American arrow poison, curare (obtained from Chondrodendron tomentosum), and is used as a muscle relaxant in surgery. Two alkaloids, vincristine and vinblastine (from Catharanthus roseus, formerly Vinca rosea), are widely used as chemotherapeutic agents in the treatment of many types of cancer.

Nicotine obtained from the tobacco plant (Nicotiana tabacum) is the principal alkaloid and chief addictive ingredient of the tobacco smoked in cigarettes, cigars, and pipes. Some alkaloids are illicit drugs and poisons. These include the hallucinogenic drugs mescaline (from Lophophora species) and psilocybin (from Psilocybe mexicana). Synthetic derivatives of the alkaloids morphine and lysergic acid (from Claviceps purpurea) produce heroin and LSD, respectively. The alkaloid coniine is the active component of the poison hemlock (Conium maculatum). Strychnine (from Strychnos species) is another powerful poison.

Special methods have been developed for isolating commercially useful alkaloids. In most cases, plant tissue is processed to obtain aqueous solutions of the alkaloids. The alkaloids are then recovered from the solution by a process called extraction, which involves dissolving some components of the mixture with reagents. Different alkaloids must then be separated and purified from the mixture. High-performance thin-layer chromatography (HPTLC) and related techniques may be used for the efficient quantitative analysis of alkaloids. Alkaloids in crystalline form may be obtained using certain solvents.