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Names | |||
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IUPAC name
(3R,4R,5S)-3-Amino-6-(hydroxymethyl)oxane-2,4,5-triol
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Other names
2-Amino-2-deoxy-glucose
Chitosamine |
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Identifiers | |||
3416-24-8 | |||
3D model (Jmol) | Interactive image | ||
1723616 | |||
ChEBI | CHEBI:5417 | ||
ChEMBL | ChEMBL181132 | ||
ChemSpider | 388352 | ||
DrugBank | DB01296 | ||
ECHA InfoCard | 100.020.284 | ||
EC Number | 222-311-2 | ||
720725 | |||
KEGG | D04334 | ||
MeSH | Glucosamine | ||
PubChem | 439213 | ||
UNII | N08U5BOQ1K | ||
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Properties | |||
C6H13NO5 | |||
Molar mass | 179.17 g·mol−1 | ||
Density | 1.563 g/mL | ||
Melting point | 150 °C (302 °F; 423 K) | ||
log P | -2.175 | ||
Acidity (pKa) | 12.273 | ||
Basicity (pKb) | 1.724 | ||
Pharmacology | |||
M01AX05 (WHO) | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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what is ?) | (|||
Infobox references | |||
Glucosamine (C6H13NO5) is an amino sugar and a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids. Glucosamine is part of the structure of the polysaccharides chitosan and chitin, which compose the exoskeletons of crustaceans and other arthropods, as well as the cell walls of fungi and many higher organisms. Glucosamine is one of the most abundant monosaccharides. It is produced commercially by the hydrolysis of crustacean exoskeletons or, less commonly, by fermentation of a grain such as corn or wheat.
The effectiveness of glucosamine has not been scientifically established for any condition, and the supplement has been shown to cause harm in high doses. Despite this, in the US it is one of the most common non-vitamin, non-mineral, dietary supplements used by adults.
Oral glucosamine is a dietary supplement and is not a pharmaceutical drug. It is illegal in the US to market any dietary supplement as a treatment for any disease or condition. Glucosamine is marketed to support the structure and function of joints, and the marketing is targeted to people suffering from osteoarthritis. Commonly sold forms of glucosamine are glucosamine sulfate, glucosamine hydrochloride, and N-acetylglucosamine. Of the three commonly available forms of glucosamine, only glucosamine sulfate is given a "likely effective" rating for treating osteoarthritis. Glucosamine is often sold in combination with other supplements such as chondroitin sulfate and methylsulfonylmethane.