Glucosamine

Glucosamine
Stereo structural formula of glucosamine ((2S,6R)-6-meth,-2-ol)
Stereo structural formula of glucosamine ((2S,6R)-6-meth,-2-ol)
Ball and stick model of glucosamine ((2R,6R)-6-meth,-2-ol)
Ball and stick model of glucosamine ((2R,6R)-6-meth,-2-ol)
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 InfoCard 100.020.284 Edit this at Wikidata
EC Number
  • 222-311-2
720725
KEGG
MeSH Glucosamine
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 ☒N
    Key: MSWZFWKMSRAUBD-SPZCMYQFSA-N ☒N
  • N[C@H]1C(O)OC(CO)[C@@H](O)[C@@H]1O
Properties
C6H13NO5
Molar mass 179.172 g·mol−1
Density 1.563 g/mL
Melting point 150 °C (302 °F; 423 K)
log P -2.175
Acidity (pKa) 7.5
Basicity (pKb) 4.5
Pharmacology
M01AX05 (WHO)
Legal status
  • EU: Authorized[1]
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.[2] Produced commercially by the hydrolysis of shellfish exoskeletons or, less commonly, by fermentation of a grain such as corn or wheat, glucosamine has many names depending on country.[3]

Although a common dietary supplement, there is little evidence that it is effective for relief of arthritis or pain, and is not an approved prescription drug in the United States.[4][5][6]

  1. ^ "List of nationally authorised medicinal products" (PDF). European Medicines Agency. 1 December 2022.
  2. ^ Cite error: The named reference carb was invoked but never defined (see the help page).
  3. ^ "Glucosamine". Drugs.com. 31 July 2019. Retrieved 14 September 2019.
  4. ^ "Glucosamine sulfate". MedlinePlus, US National Library of Medicine. 17 June 2019. Retrieved 14 September 2019.
  5. ^ "Glucosamine Hydrochloride". MedlinePlus. 8 January 2020. Archived from the original on 28 January 2020. Retrieved 27 January 2020.
  6. ^ Robert H. Shmerling (17 October 2016). "The latest on glucosamine/chondroitin supplements". Harvard Health Publishing, Harvard University Medical School. Retrieved 14 September 2019.