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Alkaloid

This article is about the class of chemical compounds. For the pharmaceutical company, see Alkaloid (company).

The first individual alkaloid, morphine, was isolated in 1804 from the opium poppy (Papaver somniferum).[1]

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[2] and even weakly acidic properties.[3] Some synthetic compounds of similar structure may also be termed alkaloids.[4] In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen or sulfur. Rarer still, they may contain elements such as phosphorus, chlorine, and bromine.[5]

Alkaloids are produced by a large variety of organisms including bacteria, fungi, plants, and animals.[6] They can be purified from crude extracts of these organisms by acid-base extraction, or solvent extractions followed by silica-gel column chromatography.[7] Alkaloids have a wide range of pharmacological activities including antimalarial (e.g. quinine), antiasthma (e.g. ephedrine), anticancer (e.g. homoharringtonine),[8] cholinomimetic (e.g. galantamine),[9] vasodilatory (e.g. vincamine), antiarrhythmic (e.g. quinidine), analgesic (e.g. morphine),[10] antibacterial (e.g. chelerythrine),[11] and antihyperglycemic activities (e.g. berberine).[12][13] Many have found use in traditional or modern medicine, or as starting points for drug discovery. Other alkaloids possess psychotropic (e.g. psilocin) and stimulant activities (e.g. cocaine, caffeine, nicotine, theobromine),[14] and have been used in entheogenic rituals or as recreational drugs. Alkaloids can be toxic too (e.g. atropine, tubocurarine).[15] Although alkaloids act on a diversity of metabolic systems in humans and other animals, they almost uniformly evoke a bitter taste.[16]

The boundary between alkaloids and other nitrogen-containing natural compounds is not clear-cut.[17] Compounds like amino acid peptides, proteins, nucleotides, nucleic acid, amines, and antibiotics are usually not called alkaloids.[2] Natural compounds containing nitrogen in the exocyclic position (mescaline, serotonin, dopamine, etc.) are usually classified as amines rather than as alkaloids.[18] Some authors, however, consider alkaloids a special case of amines.[19][20][21]

  1. ^ Luch, Andreas (2009). Molecular, Clinical and Environmental Toxicology, Volume 1: Molecular Toxicology. Vol. 1. Springer. p. 20. ISBN 9783764383367. OCLC 1056390214.
  2. ^ a b IUPAC, Compendium of Chemical Terminology, 2nd ed. (the "Gold Book") (1997). Online corrected version: (2006–) "alkaloids". doi:10.1351/goldbook.A00220
  3. ^ Manske, R. H. F. (12 May 2014). The Alkaloids: Chemistry and Physiology, Volume 8. Vol. 8. Saint Louis: Elsevier. pp. 683–695. ISBN 9781483222004. OCLC 1090491824.
  4. ^ Lewis, Robert Alan (23 March 1998). Lewis' Dictionary of Toxicology. CRC Press. p. 51. ISBN 9781566702232. OCLC 1026521889.
  5. ^ "АЛКАЛОИДЫ - Химическая энциклопедия" [Alkaloids - Chemical Encyclopedia]. www.xumuk.ru (in Russian). Retrieved 18 May 2023.
  6. ^ Roberts, M. F. (Margaret F.); Wink, Michael (1998). Alkaloids: Biochemistry, Ecology, and Medicinal Applications. Boston: Springer US. ISBN 9781475729054. OCLC 851770197.
  7. ^ Gonçalves Paterson Fox, Eduardo; Russ Solis, Daniel; Delazari dos Santos, Lucilene; Aparecido dos Santos Pinto, Jose Roberto; Ribeiro da Silva Menegasso, Anally; Cardoso Maciel Costa Silva, Rafael; Sergio Palma, Mario; Correa Bueno, Odair; de Alcântara Machado, Ednildo (April 2013). "A simple, rapid method for the extraction of whole fire ant venom (Insecta: Formicidae: Solenopsis)". Toxicon. 65: 5–8. Bibcode:2013Txcn...65....5G. doi:10.1016/j.toxicon.2012.12.009. hdl:11449/74946. PMID 23333648.
  8. ^ Kittakoop P, Mahidol C, Ruchirawat S (2014). "Alkaloids as important scaffolds in therapeutic drugs for the treatments of cancer, tuberculosis, and smoking cessation". Curr Top Med Chem. 14 (2): 239–252. doi:10.2174/1568026613666131216105049. PMID 24359196.
  9. ^ Russo P, Frustaci A, Del Bufalo A, Fini M, Cesario A (2013). "Multitarget drugs of plants origin acting on Alzheimer's disease". Curr Med Chem. 20 (13): 1686–93. doi:10.2174/0929867311320130008. PMID 23410167.
  10. ^ Raymond S. Sinatra; Jonathan S. Jahr; J. Michael Watkins-Pitchford (2010). The Essence of Analgesia and Analgesics. Cambridge University Press. pp. 82–90. ISBN 978-1139491983.
  11. ^ Cushnie TP, Cushnie B, Lamb AJ (2014). "Alkaloids: An overview of their antibacterial, antibiotic-enhancing and antivirulence activities". Int J Antimicrob Agents. 44 (5): 377–386. doi:10.1016/j.ijantimicag.2014.06.001. PMID 25130096. S2CID 205171789.
  12. ^ Singh, Sukhpal; Bansal, Abhishek; Singh, Vikramjeet; Chopra, Tanya; Poddar, Jit (June 2022). "Flavonoids, alkaloids and terpenoids: a new hope for the treatment of diabetes mellitus". Journal of Diabetes & Metabolic Disorders. 21 (1): 941–950. doi:10.1007/s40200-021-00943-8. ISSN 2251-6581. PMC 9167359. PMID 35673446.
  13. ^ Behl, Tapan; Gupta, Amit; Albratty, Mohammed; Najmi, Asim; Meraya, Abdulkarim M.; Alhazmi, Hassan A.; Anwer, Md. Khalid; Bhatia, Saurabh; Bungau, Simona Gabriela (9 September 2022). "Alkaloidal Phytoconstituents for Diabetes Management: Exploring the Unrevealed Potential". Molecules. 27 (18): 5851. doi:10.3390/molecules27185851. ISSN 1420-3049. PMC 9501853. PMID 36144587.
  14. ^ "Alkaloid". 18 December 2007.
  15. ^ Robbers JE, Speedie MK, Tyler VE (1996). "Chapter 9: Alkaloids". Pharmacognosy and Pharmacobiotechnology. Philadelphia: Lippincott, Williams & Wilkins. pp. 143–185. ISBN 978-0683085006.
  16. ^ Rhoades, David F (1979). "Evolution of Plant Chemical Defense against Herbivores". In Rosenthal, Gerald A.; Janzen, Daniel H (eds.). Herbivores: Their Interaction with Secondary Plant Metabolites. New York: Academic Press. p. 41. ISBN 978-0-12-597180-5.
  17. ^ Robert A. Meyers Encyclopedia of Physical Science and Technology – Alkaloids, 3rd edition. ISBN 0-12-227411-3
  18. ^ Cseke, Leland J.; Kirakosyan, Ara; Kaufman, Peter B.; Warber, Sara; Duke, James A.; Brielmann, Harry L. (19 April 2016). Natural Products from Plants. CRC Press. p. 30. ISBN 978-1-4200-0447-2.
  19. ^ Johnson, Alyn William (1999). Invitation to Organic Chemistry. Jones & Bartlett Learning. p. 433. ISBN 978-0-7637-0432-2.
  20. ^ Bansal, Raj K. (2003). A Textbook of Organic Chemistry. New Age International Limited. p. 644. ISBN 978-81-224-1459-2.
  21. ^ Aniszewski, p. 110

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