WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 326918
CAS#: 524-36-7 (HCl)
Description: Pyridoxamine, also known as K-163, is one form of vitamin B6. Chemically it is based on a pyridine ring structure, with hydroxyl, methyl, aminomethyl, and hydroxymethyl substituents. It differs from pyridoxine by the substituent at the 4-position. The phenol at position 3 and aminomethyl group at position 4 of its ring endow pyridoxamine with a variety of chemical properties, including the scavenging of free radical species and carbonyl species formed in sugar and lipid degradation and chelation of metal ions that catalyze Amadori reactions.
MedKoo Cat#: 326918
Name: Pyridoxamine 2HCl
CAS#: 524-36-7 (HCl)
Chemical Formula: C8H14Cl2N2O2
Exact Mass:
Molecular Weight: 241.112
Elemental Analysis: C, 39.85; H, 5.85; Cl, 29.41; N, 11.62; O, 13.27
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
The following data is based on the product molecular weight 241.112 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.
| 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 |
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.
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.
