Pyridoxamine dihydrochloride
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MedKoo CAT#: 326918

CAS#: 524-36-7 (HCl)

Description: Pyridoxamine, also known as K-163, is a form of vitamin B6.


Chemical Structure

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Pyridoxamine dihydrochloride
CAS# 524-36-7 (HCl)

Theoretical Analysis

MedKoo Cat#: 326918
Name: Pyridoxamine dihydrochloride
CAS#: 524-36-7 (HCl)
Chemical Formula: C8H14Cl2N2O2
Exact Mass: 0.00
Molecular Weight: 241.110
Elemental Analysis: C, 39.85; H, 5.85; Cl, 29.41; N, 11.62; O, 13.27

Price and Availability

Size Price Availability Quantity
1g USD 200 2 Weeks
5g USD 450
25g USD 950 2 Weeks
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Synonym: K-163; K 163; K163; Pyridoxamine; Pyridoxamine HCl; Pyridoxamine dihydrochloride

IUPAC/Chemical Name: 4-(aminomethyl)-5-(hydroxymethyl)-2-methylpyridin-3-ol dihydrochloride

InChi Key: HNWCOANXZNKMLR-UHFFFAOYSA-N

InChi Code: InChI=1S/C8H12N2O2.2ClH/c1-5-8(12)7(2-9)6(4-11)3-10-5;;/h3,11-12H,2,4,9H2,1H3;2*1H

SMILES Code: OC1=C(CN)C(CO)=CN=C1C.[H]Cl.[H]Cl

Appearance: 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 DMSO

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: Related CAS# 85-87-0 (Pyridoxamine) 524-36-7 (Pyridoxamine Dihydrochloride) Pyridoxamine was marketed as a dietary supplement, often as the hydrochloride salt, pyridoxamine dihydrochloride. However, in the United States, the FDA ruled in January 2009 that pyridoxamine must be regulated as a pharmaceutical drug because it is the active ingredient in Pyridorin, a drug designed by Biostratum, Inc., to prevent the progression of diabetic nephropathy.

Product Data:
Biological target: Pyridoxylamine dihydrochloride is an advanced glycation end production (AGEs) and lipoxidation end products (ALEs) inhibitor, to protect against diabetes-induced retinal vascular lesions.
In vitro activity: Pyridoxamine prevents insulin resistance caused by lipid hydroperoxide-derived aldehyde, specifically 4-oxo-2(E)-nonenal (ONE), which is known to induce insulin resistance by modifying proteins involved in insulin signaling. L6 skeletal muscle cells were treated with ONE, resulting in a decreased glucose uptake. Pyridoxamine treatment restored glucose uptake in these cells and prevented insulin resistance. Reference: Toxicol Res. 2022 Nov 29;39(1):147-156. https://pubmed.ncbi.nlm.nih.gov/36726824/
In vivo activity: In this study, normoglycemic mice were injected with MGO over 10 weeks to mimic hyperglycemia-related MGO surges seen in diabetic cardiovascular disease. Pyridoxamine, administered with MGO, prevented atherosclerosis in the aortic arch, reduced circulating immune cells, and lowered inflammatory gene expression, indicating its potential to mitigate vascular damage and reduce cardiovascular risk in diabetes. Reference: Biomed Pharmacother. 2023 Feb;158:114211. https://pubmed.ncbi.nlm.nih.gov/36916437/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 120.0 497.70
Water 120.0 497.70

Preparing Stock Solutions

The following data is based on the product molecular weight 241.11 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. Lee SH, Tsutsui M, Matsunaga A, Oe T. Lipid hydroperoxide-derived insulin resistance and its inhibition by pyridoxamine in skeletal muscle cells. Toxicol Res. 2022 Nov 29;39(1):147-156. doi: 10.1007/s43188-022-00155-z. PMID: 36726824; PMCID: PMC9839902. 2. Aghamohammadi M, Sirouspour M, Goncalves AS, França TCC, LaPlante SR, Shahdousti P. Modeling studies on the role of vitamins B1 (thiamin), B3 (nicotinamide), B6 (pyridoxamine), and caffeine as potential leads for the drug design against COVID-19. J Mol Model. 2022 Nov 7;28(12):380. doi: 10.1007/s00894-022-05356-9. PMID: 36342543; PMCID: PMC9640828. 3. Hanssen NMJ, Tikellis C, Pickering RJ, Dragoljevic D, Lee MKS, Block T, Scheijen JL, Wouters K, Miyata T, Cooper ME, Murphy AJ, Thomas MC, Schalkwijk CG. Pyridoxamine prevents increased atherosclerosis by intermittent methylglyoxal spikes in the aortic arches of ApoE-/- mice. Biomed Pharmacother. 2023 Feb;158:114211. doi: 10.1016/j.biopha.2022.114211. Epub 2023 Jan 3. PMID: 36916437. 4. Reeve EH, Kronquist EK, Wolf JR, Lee B, Khurana A, Pham H, Cullen AE, Peterson JA, Meza A, Colton Bramwell R, Villasana L, Machin DR, Henson GD, Walker AE. Pyridoxamine treatment ameliorates large artery stiffening and cerebral artery endothelial dysfunction in old mice. J Cereb Blood Flow Metab. 2023 Feb;43(2):281-295. doi: 10.1177/0271678X221130124. Epub 2022 Oct 2. PMID: 36189840; PMCID: PMC9903220.
In vitro protocol: 1. Lee SH, Tsutsui M, Matsunaga A, Oe T. Lipid hydroperoxide-derived insulin resistance and its inhibition by pyridoxamine in skeletal muscle cells. Toxicol Res. 2022 Nov 29;39(1):147-156. doi: 10.1007/s43188-022-00155-z. PMID: 36726824; PMCID: PMC9839902. 2. Aghamohammadi M, Sirouspour M, Goncalves AS, França TCC, LaPlante SR, Shahdousti P. Modeling studies on the role of vitamins B1 (thiamin), B3 (nicotinamide), B6 (pyridoxamine), and caffeine as potential leads for the drug design against COVID-19. J Mol Model. 2022 Nov 7;28(12):380. doi: 10.1007/s00894-022-05356-9. PMID: 36342543; PMCID: PMC9640828.
In vivo protocol: 1. Hanssen NMJ, Tikellis C, Pickering RJ, Dragoljevic D, Lee MKS, Block T, Scheijen JL, Wouters K, Miyata T, Cooper ME, Murphy AJ, Thomas MC, Schalkwijk CG. Pyridoxamine prevents increased atherosclerosis by intermittent methylglyoxal spikes in the aortic arches of ApoE-/- mice. Biomed Pharmacother. 2023 Feb;158:114211. doi: 10.1016/j.biopha.2022.114211. Epub 2023 Jan 3. PMID: 36916437. 2. Reeve EH, Kronquist EK, Wolf JR, Lee B, Khurana A, Pham H, Cullen AE, Peterson JA, Meza A, Colton Bramwell R, Villasana L, Machin DR, Henson GD, Walker AE. Pyridoxamine treatment ameliorates large artery stiffening and cerebral artery endothelial dysfunction in old mice. J Cereb Blood Flow Metab. 2023 Feb;43(2):281-295. doi: 10.1177/0271678X221130124. Epub 2022 Oct 2. PMID: 36189840; PMCID: PMC9903220.

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1: Mori Y, Kakuta T, Miyakogawa T, Takekoshi S, Yuzawa H, Kobayashi H, Kawakami A, Miyata T, Fukagawa M. Effect of Scavenging Circulating Reactive Carbonyls by Oral Pyridoxamine in Uremic Rats on Peritoneal Dialysis. Ther Apher Dial. 2016 Sep 13. doi: 10.1111/1744-9987.12446. [Epub ahead of print] PubMed PMID: 27620210.

2: Pereira-Simon S, Rubio GA, Xia X, Cai W, Choi R, Striker GE, Elliot SJ. Inhibition of Advanced Glycation End Products (AGEs) Accumulation by Pyridoxamine Modulates Glomerular and Mesangial Cell Estrogen Receptor α Expression in Aged Female Mice. PLoS One. 2016 Jul 18;11(7):e0159666. doi: 10.1371/journal.pone.0159666. eCollection 2016. PubMed PMID: 27428057; PubMed Central PMCID: PMC4948910.

3: Assimos DG. Re: Pyridoxamine and Pyridoxal are More Effective than Pyridoxine in Rescuing Folding-Defective Variants of Human Alanine:Glyoxylate Aminotransferase Causing Primary Hyperoxaluria Type I. J Urol. 2016 Apr;195(4P1):1170-1. doi: 10.1016/j.juro.2016.01.066. Epub 2016 Jan 22. PubMed PMID: 27302825.

4: Chen J, Cai D, Zhang Y. Rapid determination of lipid peroxidation using a novel pyridoxamine-participating ferrous oxidation-sulfosalicylic acid spectrophotometric method. Food Chem. 2016 Nov 15;211:637-44. doi: 10.1016/j.foodchem.2016.05.106. Epub 2016 May 17. PubMed PMID: 27283678.

5: Skrypnyk NI, Voziyan P, Yang H, de Caestecker CR, Theberge MC, Drouin M, Hudson B, Harris RC, de Caestecker MP. Pyridoxamine reduces postinjury fibrosis and improves functional recovery after acute kidney injury. Am J Physiol Renal Physiol. 2016 Aug 1;311(2):F268-77. doi: 10.1152/ajprenal.00056.2016. Epub 2016 May 18. PubMed PMID: 27194713; PubMed Central PMCID: PMC5008672.

6: Ren X, Sun H, Zhang C, Li C, Wang J, Shen J, Yu D, Kong L. Protective function of pyridoxamine on retinal photoreceptor cells via activation of the p Erk1/2/Nrf2/Trx/ASK1 signalling pathway in diabetic mice. Mol Med Rep. 2016 Jul;14(1):420-4. doi: 10.3892/mmr.2016.5270. Epub 2016 May 13. PubMed PMID: 27177199.

7: Colzani M, De Maddis D, Casali G, Carini M, Vistoli G, Aldini G. Reactivity, Selectivity, and Reaction Mechanisms of Aminoguanidine, Hydralazine, Pyridoxamine, and Carnosine as Sequestering Agents of Reactive Carbonyl Species: A Comparative Study. ChemMedChem. 2016 Aug 19;11(16):1778-89. doi: 10.1002/cmdc.201500552. Epub 2016 Feb 17. PubMed PMID: 26891408.

8: Ankisettypalli K, Cheng JJ, Baker EN, Bashiri G. PdxH proteins of mycobacteria are typical members of the classical pyridoxine/pyridoxamine 5'-phosphate oxidase family. FEBS Lett. 2016 Feb;590(4):453-60. doi: 10.1002/1873-3468.12080. Epub 2016 Feb 15. PubMed PMID: 26823273.

9: Maessen DE, Brouwers O, Gaens KH, Wouters K, Cleutjens JP, Janssen BJ, Miyata T, Stehouwer CD, Schalkwijk CG. Delayed Intervention With Pyridoxamine Improves Metabolic Function and Prevents Adipose Tissue Inflammation and Insulin Resistance in High-Fat Diet-Induced Obese Mice. Diabetes. 2016 Apr;65(4):956-66. doi: 10.2337/db15-1390. Epub 2015 Dec 30. PubMed PMID: 26718500.

10: Wong D, Hu X, Tao N, Wang X, Wang M. Effect and mechanism of pyridoxamine on the lipid peroxidation and stability of polyunsaturated fatty acids in beef patties. J Sci Food Agric. 2016 Aug;96(10):3418-23. doi: 10.1002/jsfa.7522. Epub 2015 Dec 16. PubMed PMID: 26538517.

11: Domitrovic T, Raymundo DP, da Silva TF, Palhano FL. Experimental Evidence for a Revision in the Annotation of Putative Pyridoxamine 5'-Phosphate Oxidases P(N/M)P from Fungi. PLoS One. 2015 Sep 1;10(9):e0136761. doi: 10.1371/journal.pone.0136761. eCollection 2015. PubMed PMID: 26327315; PubMed Central PMCID: PMC4556617.

12: Oppici E, Fargue S, Reid ES, Mills PB, Clayton PT, Danpure CJ, Cellini B. Pyridoxamine and pyridoxal are more effective than pyridoxine in rescuing folding-defective variants of human alanine:glyoxylate aminotransferase causing primary hyperoxaluria type I. Hum Mol Genet. 2015 Oct 1;24(19):5500-11. doi: 10.1093/hmg/ddv276. Epub 2015 Jul 21. PubMed PMID: 26199318.

13: Madu H, Avance J, Chetyrkin S, Darris C, Rose KL, Sanchez OA, Hudson B, Voziyan P. Pyridoxamine protects proteins from damage by hypohalous acids in vitro and in vivo. Free Radic Biol Med. 2015 Dec;89:83-90. doi: 10.1016/j.freeradbiomed.2015.07.001. Epub 2015 Jul 6. PubMed PMID: 26159508; PubMed Central PMCID: PMC4684779.

14: Amarnath V, Amarnath K, Avance J, Stec DF, Voziyan P. 5'-O-Alkylpyridoxamines: Lipophilic Analogues of Pyridoxamine Are Potent Scavengers of 1,2-Dicarbonyls. Chem Res Toxicol. 2015 Jul 20;28(7):1469-75. doi: 10.1021/acs.chemrestox.5b00148. Epub 2015 Jun 17. PubMed PMID: 26046387; PubMed Central PMCID: PMC4996123.

15: Wang SC, Ji HX, Hsiao CL, Wang TC, Syu YR, Miao CE, Hou LL, Lin SS, Chang WS, Tsai CW. Protective Effects of Pyridoxamine Against UVC-induced Programmed Cell Death in HaCaT Cells. In Vivo. 2015 May-Jun;29(3):379-83. PubMed PMID: 25977384.

16: Wang T, de Jesus AJ, Shi Y, Yin H. Pyridoxamine is a substrate of the energy-coupling factor transporter HmpT. Cell Discov. 2015 Jul 14;1:15014. doi: 10.1038/celldisc.2015.14. eCollection 2015. PubMed PMID: 27462413; PubMed Central PMCID: PMC4860826.

17: Dwyer JP, Greco BA, Umanath K, Packham D, Fox JW, Peterson R, Broome BR, Greene LE, Sika M, Lewis JB. Pyridoxamine dihydrochloride in diabetic nephropathy (PIONEER-CSG-17): lessons learned from a pilot study. Nephron. 2015;129(1):22-8. doi: 10.1159/000369310. Epub 2014 Dec 16. PubMed PMID: 25532068.

18: Florentinus-Mefailoski A, Marshall JG. Pyridoxamine-5-phosphate enzyme-linked immune mass spectrometric assay substrate for linear absolute quantification of alkaline phosphatase to the yoctomole range applied to prostate specific antigen. Anal Chem. 2014 Nov 4;86(21):10684-91. doi: 10.1021/ac502572a. Epub 2014 Oct 13. PubMed PMID: 25259405.

19: Sudarsanam A, Singh H, Wilcken B, Stormon M, Arbuckle S, Schmitt B, Clayton P, Earl J, Webster R. Cirrhosis associated with pyridoxal 5'-phosphate treatment of pyridoxamine 5'-phosphate oxidase deficiency. JIMD Rep. 2014;17:67-70. doi: 10.1007/8904_2014_338. Epub 2014 Sep 26. PubMed PMID: 25256445; PubMed Central PMCID: PMC4241198.

20: Wang CH, Wu ET, Wu MS, Tsai MS, Ko YH, Chang RW, Chang CY, Chang KC. Pyridoxamine protects against mechanical defects in cardiac ageing in rats: studies on load dependence of myocardial relaxation. Exp Physiol. 2014 Nov;99(11):1488-98. doi: 10.1113/expphysiol.2014.082008. Epub 2014 Sep 18. PubMed PMID: 25239923; PubMed Central PMCID: PMC4240468.