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Candicine : ウィキペディア英語版
Candicine

Candicine is a naturally occurring organic compound that is a quaternary ammonium salt with a phenethylamine skeleton. It is the N,N,N-trimethyl derivative of the well-known biogenic amine tyramine, and, being a natural product with a positively charged nitrogen atom in its molecular structure, it is classed as an alkaloid. Although it is found in a variety of plants, including barley, its properties have not been extensively studied with modern techniques. Candicine is toxic after parenteral administration, producing symptoms of neuromuscular blockade; further details are given in the "Pharmacology" section below.
==Occurrence==
Candicine occurs in a variety of plants, notably the cacti.〔T. A. Smith (1977). "Phenethylamines and related compounds in plants." ''Phytochem.'' 16 9-18.〕 This alkaloid was first isolated from the Argentinian cactus ''Trichocereus candicans'' (now reclassified as ''Echinopsis candicans''), from which it derives its name, and from other ''Trichocereus'' species. ''T. candicans'' may contain up to 5% candicine, and is also a rich source of the closely related alkaloid hordenine.〔L. Reti (1953). "β-Phenethylamines". In ''The Alkaloids'', Vol. III, (R. H. F. Manske and H. L. Holmes, Eds.), pp. 313-338, New York: Academic Press.〕
Candicine also occurs in several plants of ''Citrus'' genus.
In the late 1950s, Japanese researchers isolated a toxic compound which they named "maltoxin" from malted barley.〔N. Urakawa et al. (1959). "Some chemical and pharmacological properties of an amine (maltoxin) isolated from malt rootlet." ''Jap. J. Pharmacol.'' 9 41-45.〕 After the publication of some papers on its pharmacology (see "Pharmacology" section), under this name, it was determined that maltoxin was identical to candicine, and the older name has been retained in subsequent articles.〔N. Urukawa, Y. Hirabe and Y. Okubo (1961). "Identification of maltoxin, an active principle from malt rootlet, as candicine." ''Jap. J. Pharmacol.'' 11 4-10.〕
Candicine has also been found in the skin of the frog, ''Leptodactylus pentadactylus pentadactylus'', at a concentration of 45 μg/g skin, but it is of much more limited occurrence amongst amphibians than its positional isomer, leptodactyline.〔V. Erspamer, J. M. Cei and M. Roseghini (1963). "Occurrence of candicine (p-hydroxy phenylethyltrimethylammonium) in extracts of the skin of Leptodactylus pentadactylus pentadactylus." ''Life Sci.'' 3 825-827.〕〔M. Roseghini et al. (1986). "Indole-, imidazole- and phenyl-alkylamines in the skin of one hundred and forty American amphibian species other than Bufonids." ''Comp. Biochem. Physiol. C'' 85 139-147.〕

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