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MedKoo Cat#: 540180 | Name: Glucosamine HCl
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Glucosamine 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.

Chemical Structure

Glucosamine HCl
Glucosamine HCl
CAS#66-84-2 (HCl)

Theoretical Analysis

MedKoo Cat#: 540180

Name: Glucosamine HCl

CAS#: 66-84-2 (HCl)

Chemical Formula: C6H14ClNO5

Exact Mass: 0.0000

Molecular Weight: 215.63

Elemental Analysis: C, 33.42; H, 6.54; Cl, 16.44; N, 6.50; O, 37.10

Price and Availability

Size Price Availability Quantity
5g USD 90.00 Ready to ship
10g USD 150.00 Ready to ship
25g USD 250.00 2 Weeks
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Related CAS #
29031-19-4 (sulfate) 3416-24-8 (free base) 66-84-2 (HCl)
Synonym
Glucosamine HCl; Chitosamine HCl; NSC 234443; NSC234443; NSC-234443; NSC 758; NSC758; NSC-758
IUPAC/Chemical Name
(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)tetrahydro-2H-pyran-2,4,5-triol hydrochloride
InChi Key
QKPLRMLTKYXDST-NSEZLWDYSA-N
InChi Code
InChI=1S/C6H13NO5.ClH/c7-3-5(10)4(9)2(1-8)12-6(3)11;/h2-6,8-11H,1,7H2;1H/t2-,3-,4-,5-,6?;/m1./s1
SMILES Code
O[C@H]1[C@H](O)[C@@H](N)C(O)O[C@@H]1CO.[H]Cl
Appearance
White to off-white solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
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. Glucosamine, along with commonly used chondroitin, is not routinely prescribed to treat people who have symptomatic osteoarthritis of the knee, as there is insufficient evidence that this treatment is helpful. As is common with heavily promoted dietary supplements, the claimed benefits of glucosamine are based principally on clinical and laboratory studies. Clinical studies are divided, with some reporting relief from arthritic pain and stiffness, while higher quality studies report no benefit above placebo. There is no evidence to date that consumption of glucosamine by sport participants will prevent or limit joint damage after injury. In a randomized placebo-controlled trial, glucosamine supplementation had no additional effect on any rehabilitation outcome when given to athletes after anterior cruciate ligament (ACL) reconstruction.
Biological target:
Glucosamine hydrochloride (D-Glucosamine hydrochloride) is a prominent precursor in the biochemical synthesis of glycosylated proteins and lipids.
In vitro activity:
To fully confirm the role of glucosamine in lung tissues after radiation, this study utilized immunofluorescence staining to check the changes of epithelial marker (E-cadherin) and interstitial markers (α-SMA and Vimentin) in lung tissues at 1 week and 8 week after radiation. Figure 1C-H,J-L showed that glucosamine could significantly inhibit the overexpression of interstitial markers α-SMA and Vimentin, and inhibit the down-regulation of interstitial markers E-cadherin caused by radiation. The effect of WR2721 was weaker than glucosamine treatment. The content of related markers in lung tissues was also tested at 1 week and 8 weeks after radiation (Figure 2A-D), which showed the consistent results with immunofluorescence staining. Reference: J Cell Mol Med. 2020 Sep; 24(18): 11018–11023. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7521322/
In vivo activity:
The GLN treatment (10 and 30 mg/mouse) was able to increase the CREB5 mRNA concentration, but decreased PDE4B mRNA levels in the hippocampus (Figure 3A). The cAMP concentration in the hippocampal tissue elevated after GLN treatment (Figure 3B). Meanwhile, the corresponding downstream signal activation of the cAMP/PKA in terms of CREB phosphorylation in the hippocampus seemed to be promoted by GLN (Figure 3C). In addition, this study examined the GLN effect on regulation of the BDNF, CREB5 and PDE4B genes in HT22 cells. The GLN treatment (10 mM) increased the mRNA levels of BDNF, CREB5 and PDE4B (Figure 3D), while both BDNF and CREB5 protein levels were increased by GLN (1 and 10 mM), but the PDE4B protein expression remained unaffected by GLN (Figure 3E,F). Reference: Molecules. 2020 Aug; 25(16): 3667. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7465318/
Solvent mg/mL mM
Solubility
DMSO 52.0 241.15
PBS (pH 7.2) 10.0 46.38
Water 46.5 215.65
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 215.63 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Lei X, Ma N, Liang Y, Liu J, Zhang P, Han Y, Chen W, Du L, Qu B. Glucosamine protects against radiation-induced lung injury via inhibition of epithelial-mesenchymal transition. J Cell Mol Med. 2020 Sep;24(18):11018-11023. doi: 10.1111/jcmm.15662. Epub 2020 Jul 22. PMID: 32700471; PMCID: PMC7521322. 2. Chen CL, Chen YH, Liang CM, Tai MC, Lu DW, Chen JT. Glucosamine-Induced Autophagy through AMPK⁻mTOR Pathway Attenuates Lipofuscin-Like Autofluorescence in Human Retinal Pigment Epithelial Cells In Vitro. Int J Mol Sci. 2018 May 9;19(5):1416. doi: 10.3390/ijms19051416. PMID: 29747425; PMCID: PMC5983587. 3. Chou LY, Chao YM, Peng YC, Lin HC, Wu YL. Glucosamine Enhancement of BDNF Expression and Animal Cognitive Function. Molecules. 2020 Aug 12;25(16):3667. doi: 10.3390/molecules25163667. PMID: 32806562; PMCID: PMC7465318. 4. Lin Y, Wu C, Wang X, Liu S, Zhao K, Kemper T, Yu H, Li M, Zhang J, Chen M, Zhu Y, Chen X, Lu M. Glucosamine promotes hepatitis B virus replication through its dual effects in suppressing autophagic degradation and inhibiting MTORC1 signaling. Autophagy. 2020 Mar;16(3):548-561. doi: 10.1080/15548627.2019.1632104. Epub 2019 Jun 23. PMID: 31204557; PMCID: PMC6999643.
In vitro protocol:
1. Lei X, Ma N, Liang Y, Liu J, Zhang P, Han Y, Chen W, Du L, Qu B. Glucosamine protects against radiation-induced lung injury via inhibition of epithelial-mesenchymal transition. J Cell Mol Med. 2020 Sep;24(18):11018-11023. doi: 10.1111/jcmm.15662. Epub 2020 Jul 22. PMID: 32700471; PMCID: PMC7521322. 2. Chen CL, Chen YH, Liang CM, Tai MC, Lu DW, Chen JT. Glucosamine-Induced Autophagy through AMPK⁻mTOR Pathway Attenuates Lipofuscin-Like Autofluorescence in Human Retinal Pigment Epithelial Cells In Vitro. Int J Mol Sci. 2018 May 9;19(5):1416. doi: 10.3390/ijms19051416. PMID: 29747425; PMCID: PMC5983587.
In vivo protocol:
1. Chou LY, Chao YM, Peng YC, Lin HC, Wu YL. Glucosamine Enhancement of BDNF Expression and Animal Cognitive Function. Molecules. 2020 Aug 12;25(16):3667. doi: 10.3390/molecules25163667. PMID: 32806562; PMCID: PMC7465318. 2. Lin Y, Wu C, Wang X, Liu S, Zhao K, Kemper T, Yu H, Li M, Zhang J, Chen M, Zhu Y, Chen X, Lu M. Glucosamine promotes hepatitis B virus replication through its dual effects in suppressing autophagic degradation and inhibiting MTORC1 signaling. Autophagy. 2020 Mar;16(3):548-561. doi: 10.1080/15548627.2019.1632104. Epub 2019 Jun 23. PMID: 31204557; PMCID: PMC6999643.
1: Al-Hamidi H, Edwards AA, Douroumis D, Asare-Addo K, Nayebi AM, Reyhani-Rad S, Mahmoudi J, Nokhodchi A. Effect of glucosamine HCl on dissolution and solid state behaviours of piroxicam upon milling. Colloids Surf B Biointerfaces. 2013 Mar 1;103:189-99. doi: 10.1016/j.colsurfb.2012.10.023. Epub 2012 Nov 5. PubMed PMID: 23201737. 2: Al-Hamidi H, Asare-Addo K, Desai S, Kitson M, Nokhodchi A. The dissolution and solid-state behaviours of coground ibuprofen-glucosamine HCl. Drug Dev Ind Pharm. 2015;41(10):1682-92. doi: 10.3109/03639045.2014.991401. Epub 2014 Dec 11. PubMed PMID: 25496174. 3: Jo JR, Park YK, Jang BC. Short-term treatment with glucosamine hydrochloride specifically downregulates hypoxia-inducible factor-1α at the protein level in YD-8 human tongue cancer cells. Int J Oncol. 2014 May;44(5):1699-706. doi: 10.3892/ijo.2014.2336. Epub 2014 Mar 11. PubMed PMID: 24626348. 4: Henry N, Favetta P, Delépée R, Seigneuret JM, Agrofoglio LA. Synthesis of a molecularly imprinted polymer to isolate glucosamine from plant extracts by an ionic-non-covalent dual approach. Int J Cosmet Sci. 2015 Apr;37(2):196-206. doi: 10.1111/ics.12182. Epub 2015 Jan 20. PubMed PMID: 25400098. 5: Ohmi Y, Nishimura S, Ebitani K. Synthesis of α-amino acids from glucosamine-HCl and its derivatives by aerobic oxidation in water catalyzed by Au nanoparticles on basic supports. ChemSusChem. 2013 Dec;6(12):2259-62. doi: 10.1002/cssc.201300303. Epub 2013 Aug 12. PubMed PMID: 23940001. 6: Kulkarni C, Leena A, Lohit K, Mishra D, Saji MJ. A randomized comparative study of safety and efficacy of immediate release glucosamine HCL and glucosamine HCL sustained release formulation in the treatment of knee osteoarthritis: A proof of concept study. J Pharmacol Pharmacother. 2012 Jan;3(1):48-54. doi: 10.4103/0976-500X.92515. PubMed PMID: 22368417; PubMed Central PMCID: PMC3284037. 7: Damlar I, Esen E, Tatli U. Effects of glucosamine-chondroitin combination on synovial fluid IL-1β, IL-6, TNF-α and PGE2 levels in internal derangements of temporomandibular joint. Med Oral Patol Oral Cir Bucal. 2015 May 1;20(3):e278-83. PubMed PMID: 25662545; PubMed Central PMCID: PMC4464914. 8: Park J, Lee SY, Ooshima A, Yang KM, Kang JM, Kim YW, Kim SJ. Glucosamine hydrochloride exerts a protective effect against unilateral ureteral obstruction-induced renal fibrosis by attenuating TGF-β signaling. J Mol Med (Berl). 2013 Nov;91(11):1273-84. doi: 10.1007/s00109-013-1086-1. Epub 2013 Sep 27. PubMed PMID: 24072041; PubMed Central PMCID: PMC3825548. 9: Al-Kurdi ZI, Chowdhry BZ, Leharne SA, Qinna NA, Al Omari MM, Badwan AA. Influence of glucosamine on the bioactivity of insulin delivered subcutaneously and in an oral nanodelivery system. Drug Des Devel Ther. 2015 Nov 19;9:6167-76. doi: 10.2147/DDDT.S91974. eCollection 2015. PubMed PMID: 26640369; PubMed Central PMCID: PMC4657806. 10: Wu B, Bai Z, Meng X, He B. Efficient production of D-glucosaminic acid from D-glucosamine by Pseudomonas putida GNA5. Biotechnol Prog. 2011 Jan-Feb;27(1):32-7. doi: 10.1002/btpr.529. Epub 2010 Dec 23. PubMed PMID: 21312352. 11: Park SH, Hong H, Han YM, Kangwan N, Kim SJ, Kim EH, Hahm KB. Nonsteroidal anti-inflammatory drugs (NSAID) sparing effects of glucosamine hydrochloride through N-glycosylation inhibition; strategy to rescue stomach from NSAID damage. J Physiol Pharmacol. 2013 Apr;64(2):157-65. PubMed PMID: 23756390. 12: Jung CW, Jo JR, Lee SH, Park YK, Jung NK, Song DK, Bae J, Nam KY, Ha JS, Park IS, Park GY, Jang BC, Park JW. Anti-cancer properties of glucosamine-hydrochloride in YD-8 human oral cancer cells: Induction of the caspase-dependent apoptosis and down-regulation of HIF-1α. Toxicol In Vitro. 2012 Feb;26(1):42-50. doi: 10.1016/j.tiv.2011.10.005. Epub 2011 Oct 13. PubMed PMID: 22020377. 13: Ebube NK, Mark W, Hahm H. Preformulation studies and characterization of proposed chondroprotective agents: glucosamine HCl and chondroitin sulfate. Pharm Dev Technol. 2002 Nov;7(4):457-69. PubMed PMID: 12503527. 14: Al-Hamidi H, Edwards AA, Mohammad MA, Nokhodchi A. Glucosamine HCl as a new carrier for improved dissolution behaviour: effect of grinding. Colloids Surf B Biointerfaces. 2010 Nov 1;81(1):96-109. doi: 10.1016/j.colsurfb.2010.06.028. Epub 2010 Jul 6. PubMed PMID: 20674291. 15: Al-Hamidi H, Obeidat WM, Nokhodchi A. The dissolution enhancement of piroxicam in its physical mixtures and solid dispersion formulations using gluconolactone and glucosamine hydrochloride as potential carriers. Pharm Dev Technol. 2015 Jan;20(1):74-83. doi: 10.3109/10837450.2013.871029. Epub 2014 Jan 6. PubMed PMID: 24392858. 16: Terencio MC, Ferrándiz ML, Carceller MC, Ruhí R, Dalmau P, Vergés J, Montell E, Torrent A, Alcaraz MJ. Chondroprotective effects of the combination chondroitin sulfate-glucosamine in a model of osteoarthritis induced by anterior cruciate ligament transection in ovariectomised rats. Biomed Pharmacother. 2016 Apr;79:120-8. doi: 10.1016/j.biopha.2016.02.005. Epub 2016 Feb 18. PubMed PMID: 27044820. 17: Leatherwood JL, Gehl KL, Coverdale JA, Arnold CE, Dabareiner RA, Walter KN, Lamprecht ED. Influence of oral glucosamine supplementation in young horses challenged with intra-articular lipopolysaccharide. J Anim Sci. 2016 Aug;94(8):3294-3302. PubMed PMID: 27695773. 18: Aghazadeh-Habashi A, Jamali F. The glucosamine controversy; a pharmacokinetic issue. J Pharm Pharm Sci. 2011;14(2):264-73. Review. PubMed PMID: 21733414. 19: Walsh AJ, O'neill CW, Lotz JC. Glucosamine HCl alters production of inflammatory mediators by rat intervertebral disc cells in vitro. Spine J. 2007 Sep-Oct;7(5):601-8. Epub 2007 Jan 2. PubMed PMID: 17905323. 20: Sanches-Silva A, Ribeiro T, Albuquerque TG, Paseiro P, Sendón R, de Quirós AB, López-Cervantes J, Sánchez-Machado DI, Valdez HS, Angulo I, Aurrekoetxea GP, Costa HS. Ultra-high pressure LC determination of glucosamine in shrimp by-products and migration tests of chitosan films. J Sep Sci. 2012 Mar;35(5-6):633-40. doi: 10.1002/jssc.201100855. PubMed PMID: 22517638.