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synephrine : ウィキペディア英語版
synephrine

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''This article will focus, insofar as possible, on synephrine itself, rather than on the drug mixtures containing it.''
Synephrine, or, more specifically, ''p''-synephrine, is an alkaloid, occurring naturally in some plants and animals, and also in approved drugs products as its ''m''-substituted analog known as neo-synephrine. ''p''-synephrine (or formerly Sympatol and oxedrine (HREF="http://www.kotoba.ne.jp/word/11/British Approved Name" TITLE="British Approved Name">BAN )) and ''m''-synephrine are known for their longer acting adrenergic effects compared to norepinephrine. This substance is present at very low concentrations in common foodstuffs such as orange juice and other orange (''Citrus'' species) products, both of the "sweet" and "bitter" variety. The preparations used in Traditional Chinese Medicine (TCM), also known as Zhi Shi, are the immature and dried whole oranges from ''Citrus aurantium'' (Fructus Aurantii Immaturus). Extracts of the same material or purified synephrine are also marketed in the US, sometimes in combination with caffeine, as a weight-loss-promoting dietary supplement for oral consumption. While the traditional preparations have been in use for millennia as a component of TCM-formulas, synephrine itself is not an approved OTC drug. As a pharmaceutical, ''m''-synephrine is still used as a sympathomimetic (i.e. for its hypertensive and vasoconstrictor properties), mostly by injection for the treatment of emergencies such as shock, and rarely orally for the treatment of bronchial problems associated with asthma and hay-fever.
It is important to distinguish between studies concerning synephrine as a single chemical entity (and even here it should be borne in mind that synephrine can exist in the form of either of two stereoisomers, d- and l-synephrine, which are chemically and pharmacologically distinct), and synephrine which is mixed with other drugs and/or botanical extracts in a "Supplement", as well as synephrine which is present as only one chemical component in a naturally-occurring mixture of phytochemicals such as the rind or fruit of a bitter orange. Mixtures containing synephrine as only one of their chemical components (regardless of whether these are of synthetic or natural origin) should not be assumed to produce exactly the same biological effects as synephrine alone.〔H. Wagner and G. Ulrich-Merzenich (2009). "Synergy research: approaching a new generation of phytopharmaceuticals." ''Phytomed.'' 16 97-110.〕
In physical appearance, synephrine is a colorless, crystalline solid and is water-soluble. Its molecular structure is based on a phenethylamine skeleton, and is related to those of many other drugs, and to the major neurotransmitters epinephrine and norepinephrine.
== Natural occurrences ==
Synephrine, although already known as a synthetic organic compound, was first isolated as a natural product from the leaves of various ''Citrus'' trees, and its presence noted in different ''Citrus'' juices, by Stewart and co-workers in the early 1960s.〔I. Stewart, W. F. Newhall, and G. J. Edwards (1964). "The isolation and identification of synephrine in the leaves and fruit of Citrus." ''J. Biol. Chem.'' 239 930-932.〕〔()〕 A survey of the distribution of synephrine amongst the higher plants was published in 1970 by Wheaton and Stewart.〔T. A. Wheaton and I. Stewart (1970). "The distribution of tyramine, N-methyltyramine, hordenine, octopamine and synephrine in higher plants. ''Lloydia'' 33 244-254.〕 It has subsequently been detected in ''Evodia''〔H. C. Ko, K. T. Chen, C. F. Chen, J. P. Su, C. M. Chen, and G. J. Wang (2006). "Chemical and biological comparisons on ''Evodia'' with two related species of different locations and conditions." ''J. Ethnopharmacol.'' 108 257-263.〕 and ''Zanthoxylum'' species,〔J. A. Swinehart, and F. R. Stermitz (1980). "Bishordeninyl terpene alkaloids and other constituents of ''Zanthoxylum culantrillo'' and ''Z. coriaceum''. ''Phytochem.'' 19 1219-1223.〕 all plants of the family Rutaceae.
Trace levels (0.003%) of synephrine have also been detected in the dried leaves of ''Pogostemon cablin'' (patchouli, Lamiaceae).〔S. P. Kim, E. Moon, S. H. Nam, and M. Friedman (2012). "Composition of Herba Pogostemonis water extract and protection of infected mice against ''Salmonella typhimurium''-induced liver damage and mortality by stimulation of innate immune cells." ''J. Agric. Food Chem.'' 60 12122–12130.〕 It is also found in certain cactus species of the genera ''Coryphantha'' and ''Dolichothele''.
However, this compound is found predominantly in a number of ''Citrus'' species, including "bitter" and "sweet" orange varieties.

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