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Topic summary

Glucosamine

Glucosamine
Names IUPAC name
2-Amino-2-deoxy-glucose
Systematic IUPAC name
(3R,4R,5S)-3-Amino-6-(hydroxymethyl)oxane-2,4,5-triol
Other names
Chitosamine
Identifiers
3D model (JSmol)
1723616 ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard100.020.284EC Number
  • 222-311-2
720725 KEGG
MeSHGlucosamine
UNII
  • InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2?,3-,4-,5-,6?/m1/s1
    Key: MSWZFWKMSRAUBD-SPZCMYQFSA-N
  • N[C@H]1C(O)OC(CO)[C@@H](O)[C@@H]1O
Properties C6H13NO5Molar mass179.172 g·mol Density1.563 g/mL Melting point150 °C (302 °F; 423 K) log P−2.175 Acidity (pKa) 7.5 Basicity (pKb) 4.5 Pharmacology M01AX05 (WHO) Legal status
  • EU: Authorized
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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 two polysaccharides, chitosan and chitin. Glucosamine is one of the most abundant monosaccharides. It is produced commercially by the hydrolysis of shellfishexoskeletons or, less commonly, by fermentation of a grain such as corn or wheat. Glucosamine has various names depending on the country and its intended use.

Although a common dietary supplement, there is little clinical evidence that it is effective for relief of arthritis or pain, and is not an approved prescription drug in most countries, although it is listed as a medicinal product in Europe. Worldwide, there are no clinical organizations that recommend use of glucosamine as a treatment for arthritis.

Wikipedia source