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16-September-2008 16:15:18 - Alkaloid This article is about the chemical compounds alkaloids. For the pharmaceutical company in the Republic of Macedonia see Alkaloid company. Chemical structure of ephedrine, a phenethylamine alkaloid Chemical structure of ephedrine, a phenethylamine alkaloid Alkaloids are naturally occurring chemical compounds containing basic nitrogen atoms. The name derives from the word alkaline and was used to describe any nitrogen-containing base. Alkaloids are produced by a large variety of organisms, including bacteria, fungi, plants, and animals and are part of the group of natural products also called secondary metabolites. Many alkaloids can be purified from crude extracts by acid-base extraction. Many alkaloids are toxic to other organisms. They often have pharmacological effects and are used as medications and recreational drugs. Examples are the local anesthetic and stimulant cocaine, the stimulant caffeine, nicotine, the analgesic morphine, or the antimalarial drug quinine. Some alkaloids have a bitter taste. Caffeine Caffeine Contents 1 Alkaloid classifications 2 Physicochemical properties 3 See also 4 References Alkaloid classifications Alkaloids are usually classified by their common molecular precursors, based on the metabolic pathway used to construct the molecule. When not much was known about the biosynthesis of alkaloids, they were grouped under the names of known compounds, even some non-nitrogenous ones since those molecules' structures appear in the finished product; the opium alkaloids are sometimes called phenanthrenes, for example, or by the plants or animals they were isolated from. When more is learned about a certain alkaloid, the grouping is changed to reflect the new knowledge, usually taking the name of a biologically-important amine that stands out in the synthesis process. Pyridine group: piperine, coniine, trigonelline, arecoline, arecaidine, guvacine, cytisine, lobeline, nicotine, anabasine, sparteine, pelletierine. Pyrrolidine group: hygrine, cuscohygrine, nicotine Tropane group: atropine, cocaine, ecgonine, scopolamine, catuabine Quinoline group: quinine, quinidine, dihydroquinine, dihydroquinidine, strychnine, brucine, veratrine, cevadine Isoquinoline group: opium alkaloids papaverine, narcotine, narceine, sanguinarine, hydrastine, berberine, emetine, berbamine, oxyacanthine Phenanthrene alkaloids: The opium alkaloids morphine, codeine, thebaine Phenethylamine group: mescaline, ephedrine, dopamine, amphetamine Indole group: Tryptamines: serotonin, DMT, 5-MeO-DMT, bufotenine, psilocybin Ergolines the ergot alkaloids: ergine, ergotamine, lysergic acid, LSD Beta-carbolines: harmine, harmaline, tetrahydroharmine Yohimbans: reserpine, yohimbine Vinca alkaloids: vinblastine, vincristine Mitragyna speciosa alkaloids: mitragynine, 7-hydroxymitragynine Tabernanthe iboga alkaloids: ibogaine, voacangine, coronaridine, 18-methoxycoronaridine Strychnos nux-vomica alkaloids: strychnine, brucine Purine group: Xanthines: caffeine, theobromine, theophylline Terpenoid group: Aconite alkaloids: aconitine Steroid alkaloids containing a steroid skeleton in a nitrogen containing structure: solanum e.g. potato and tomato alkaloids solanidine, solanine, chaconine veratrum alkaloids veratramine, cyclopamine, cycloposine, jervine, muldamine1 newt alkaloids samandarin others conessine Quaternary ammonium compounds: muscarine, choline, neurine Miscellaneous: capsaicin, cynarin, phytolaccine, phytolaccotoxin Physicochemical properties Low-molecular weight alkaloids without hydrogen bond donors such as hydroxy groups are often liquid at room temperature, examples are nicotine, sparteine, coniine, and phenethylamine. The basicity of alkaloids depends on the lone pairs of electrons on their nitrogen atoms. As organic bases, alkaloids form salts with mineral acids such as hydrochloric acid and sulfuric acid and organic acids such as tartaric acid or maleic acid. These salts are usually more water-soluble than their free base form. See also Amine Base chemistry Natural products Secondary metabolite References Wikimedia Commons has media related to: Alkaloid ^ http://www.ansci.cornell.edu/plants/toxicagents/steroid.html, v d e Alkaloid groups Indole: 5-MeO-DMT | Dimethyltryptamine | Harmala alkaloids | Psilocin | Psilocybin | Reserpine | Serotonin | Tryptamine | Yohimbine Phenethylamine: Amphetamine | Cathinone | Ephedrine | Mescaline | Methamphetamine | Phenethylamine | Tyramine Purine: Caffeine | Theobromine | Theophylline Pyridine: Coniine Pyrrolidine: Nicotine Quinoline: Quinine Isoquinoline: Codeine | Morphine Tropane: Atropine | Cocaine | Hyoscyamine | Scopolamine Terpenoid: Aconitine | Solanine Betaines: Choline | Muscarine Major families of biochemicals Saccharides | Carbohydrates | Glycosides | | Amino acids | Peptides | Proteins | Glycoproteins | | Lipids | Terpenes | Steroids | Carotenoids Alkaloids | Nucleobases | Nucleic acids | | Enzyme cofactors | Flavonoids | Polyketides | Tetrapyrroles Retrieved from http://en..org/wiki/Alkaloid Categories: Metabolism | Natural products | Alkaloids Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages العربية БългарÑ?ки Català Česky Dansk Deutsch Eesti Español Esperanto Ù?ارسی Français Galego Hrvatski Italiano עברית LatvieÅ¡u Lietuvių Magyar Nederlands ‪Norsk bokmÃ¥l‬ ‪Norsk nynorsk‬ Polski Português Română РуÑ?Ñ?кий Shqip SlovenÄ?ina SlovenÅ¡Ä?ina СрпÑ?ки / Srpski Srpskohrvatski / СрпÑ?кохрватÑ?ки Suomi Svenska Tiếng Việt Türkçe УкраїнÑ?ька 䏿–‡ This page was last modified on 9 August 2008, at 06:34
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