Difference between revisions of "Alkaloid" - New World Encyclopedia
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[[Image:Ephedrine.png|thumb|Chemical structure of [[ephedrine]], a phenethylamine alkaloid]] | [[Image:Ephedrine.png|thumb|Chemical structure of [[ephedrine]], a phenethylamine alkaloid]] | ||
| − | An '''alkaloid''' is, strictly speaking, a naturally occurring [[amine]] produced by a [[plant]], but amines produced by [[animal]]s and [[fungus|fungi]] are also called alkaloids<ref>{{cite book | last = Carey | first = Francis A. | title = Organic Chemistry | origyear = 1987 | edition = 6th ed. | year = 2006 | publisher = McGraw Hill | location = New York | id = ISBN 0-07-282837-4 | pages = 954 | quote = (Strictly speaking, these compounds are not classified as alkaloids because they are not isolated from plants.)}}</ref>. Many alkaloids have [[pharmacology|pharmacological]] effects on [[human]]s and other | + | An '''alkaloid''' is, strictly speaking, a naturally occurring [[amine]] produced by a [[plant]], but amines produced by [[animal]]s and [[fungus|fungi]] are also called alkaloids<ref>{{cite book | last = Carey | first = Francis A. | title = Organic Chemistry | origyear = 1987 | edition = 6th ed. | year = 2006 | publisher = McGraw Hill | location = New York | id = ISBN 0-07-282837-4 | pages = 954 | quote = (Strictly speaking, these compounds are not classified as alkaloids because they are not isolated from plants.)}}</ref>. Many alkaloids have [[pharmacology|pharmacological]] effects on [[human]]s and other animals. The name derives from the word [[alkaline]]; originally, the term was used to describe any [[nitrogen]]-containing [[base (chemistry)|base]]. Alkaloids are usually derivatives of [[amino acids]], and many have a [[Bitter (taste)#Bitterness|bitter taste]]. They are found as [[secondary metabolite]]s in plants (e.g. [[potato]]es and [[tomato]]es), animals (e.g. [[shellfish]]) and fungi. Many alkaloids can be purified from crude extracts by [[acid-base extraction]]. |
While many alkaloids are [[poison]]ous, some are used medicinally as [[analgesic]]s (pain relievers) or [[anaesthetic]]s, particularly [[morphine]] and [[codeine]], and for other uses. | While many alkaloids are [[poison]]ous, some are used medicinally as [[analgesic]]s (pain relievers) or [[anaesthetic]]s, particularly [[morphine]] and [[codeine]], and for other uses. | ||
== Alkaloid classifications == | == Alkaloid classifications == | ||
| − | Alkaloids are usually classified by their common molecular feat, 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" | + | Alkaloids are usually classified by their common [[molecule|molecular]] feat, 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]], [[arecaidine]], [[guvacine]], [[pilocarpine]], [[cytisine]], [[nicotine]], [[sparteine]], [[pelletierine]]. | * [[Pyridine]] group: [[piperine]], [[coniine]], [[trigonelline]], [[arecaidine]], [[guvacine]], [[pilocarpine]], [[cytisine]], [[nicotine]], [[sparteine]], [[pelletierine]]. | ||
* [[Pyrrolidine]] group: [[hygrine]], [[cuscohygrine]], [[nicotine]] | * [[Pyrrolidine]] group: [[hygrine]], [[cuscohygrine]], [[nicotine]] | ||
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** [[Aconite]] alkaloids: [[aconitine]] | ** [[Aconite]] alkaloids: [[aconitine]] | ||
** [[Steroid]]s: [[solanine]], [[samandari]]s ([[ammonium|quaternary ammonium compound]]s): [[muscarine]], [[choline]], [[neurine]] | ** [[Steroid]]s: [[solanine]], [[samandari]]s ([[ammonium|quaternary ammonium compound]]s): [[muscarine]], [[choline]], [[neurine]] | ||
| − | * Vinca alkaloids: [[vinblastine]], [[vincristine]]. They are antineoplastic and binds free tubulin dimers thereby disrupting balance between | + | * Vinca alkaloids: [[vinblastine]], [[vincristine]]. They are antineoplastic and binds free tubulin dimers thereby disrupting balance between microtubule polymerization and depolymerization resulting in arrest of cells in [[metaphase]]. |
== Physicochemical Properties of Alkaloids == | == Physicochemical Properties of Alkaloids == | ||
* Molecular weight 100-900 | * Molecular weight 100-900 | ||
| − | * Those without oxygen atoms in the structure are usually liquid at ordinary temperature (e.g. nicotine, sparteine, coniine) | + | * Those without [[oxygen]] atoms in the structure are usually liquid at ordinary [[temperature]] (e.g. nicotine, sparteine, coniine) |
* Those with oxygen atoms are crystalline (e.g. berberine) | * Those with oxygen atoms are crystalline (e.g. berberine) | ||
* Most are optically active, but not those from the purine group | * Most are optically active, but not those from the purine group | ||
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{{IPA|}} | {{IPA|}} | ||
| − | == | + | == Notes == |
{{Commons|Alkaloid}} | {{Commons|Alkaloid}} | ||
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{{alkaloids}} | {{alkaloids}} | ||
| − | [[Category: | + | [[Category:Physical sciences]] |
| − | [[Category: | + | [[Category:Chemistry]] |
| − | + | [[Category:Biochemistry]] | |
{{credits|Alkaloid|159535891}} | {{credits|Alkaloid|159535891}} | ||
Revision as of 13:28, 22 September 2007
An alkaloid is, strictly speaking, a naturally occurring amine produced by a plant, but amines produced by animals and fungi are also called alkaloids[1]. Many alkaloids have pharmacological effects on humans and other animals. The name derives from the word alkaline; originally, the term was used to describe any nitrogen-containing base. Alkaloids are usually derivatives of amino acids, and many have a bitter taste. They are found as secondary metabolites in plants (e.g. potatoes and tomatoes), animals (e.g. shellfish) and fungi. Many alkaloids can be purified from crude extracts by acid-base extraction. While many alkaloids are poisonous, some are used medicinally as analgesics (pain relievers) or anaesthetics, particularly morphine and codeine, and for other uses.
Alkaloid classifications
Alkaloids are usually classified by their common molecular feat, 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, arecaidine, guvacine, pilocarpine, cytisine, nicotine, 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: The opium alkaloids (morphine, codeine, thebaine, Isopapa-dimethoxy-aniline, papaverine, narcotine, sanguinarine, narceine, hydrastine, berberine)
- Phenethylamine group: mescaline, ephedrine, dopamine, amphetamine
- Indole group:
- Tryptamines: DMT, N-methyltryptamine, psilocybin, serotonin
- Ergolines: the ergot alkaloids (ergine, ergotamine, lysergic acid, etc.)
- Beta-carbolines: harmine, harmaline, yohimbine, reserpine, emetine
- Rauwolfia alkaloids: Reserpine
- Purine group:
- Xanthines: caffeine, theobromine, theophylline
- Terpenoid group:
- Vinca alkaloids: vinblastine, vincristine. They are antineoplastic and binds free tubulin dimers thereby disrupting balance between microtubule polymerization and depolymerization resulting in arrest of cells in metaphase.
Physicochemical Properties of Alkaloids
- Molecular weight 100-900
- Those without oxygen atoms in the structure are usually liquid at ordinary temperature (e.g. nicotine, sparteine, coniine)
- Those with oxygen atoms are crystalline (e.g. berberine)
- Most are optically active, but not those from the purine group
- Basicity depends on the availability of lone pairs of electrons on the N atom & the type of heterocycle and substituents.
- Ability to form salts with mineral acids (e.g. with HCl, H2SO4, HNO3) or organic acids (e.g. tartrates, sulfamates, maleates)
Notes
- ↑ Carey, Francis A. [1987] (2006). Organic Chemistry, 6th ed., New York: McGraw Hill, 954. ISBN 0-07-282837-4. “(Strictly speaking, these compounds are not classified as alkaloids because they are not isolated from plants.)”
| Major families of biochemicals | ||
| Peptides | Amino acids | Nucleic acids | Carbohydrates | Nucleotide sugars | Lipids | Terpenes | Carotenoids | Tetrapyrroles | Enzyme cofactors | Steroids | Flavonoids | Alkaloids | Polyketides | Glycosides | ||
| Analogues of nucleic acids: | Types of Alkaloids | Analogues of nucleic acids: |
| General: | ||
|---|---|---|
| Indole group: | 5-MeO-DMT | Dimethyltryptamine | Harmala alkaloids | Psilocin | Psilocybin | Reserpine | Serotonin | Tryptamine | Yohimbine | |
| Phenethylamine group: | Amphetamine | Cathinone | Ephedrine | Mescaline | Methamphetamine | Phenethylamine | Tyramine | |
| Purine group: | Caffeine | Theobromine | Theophylline | |
| Pyridine group: | Coniine | |
| Pyrrolidine group: | Nicotine | |
| Quinoline group: | Quinine | |
| Isoquinoline group: | Codeine | Morphine | |
| Tropane group: | Atropine | Cocaine | Hyoscyamine | Scopolamine | |
| Terpenoid group: | Aconitine | Solanine | |
| Betaines: | Choline | Muscarine | |
| Pyrazole group: | ||
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