A degradation product of methylene blue

Arkivoc

Volumn 2003, Issue 1, 2003, Pages 37-42

  Plater, M John ^a  

^a UNIVERSITY OF ABERDEEN   (United Kingdom)

Author keywords

Metabolite; Methylene blue

Indexed keywords

ALKALI; BROMINE; DRUG METABOLITE; METHYLENE BLUE; METHYLENE VIOLET; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; DRUG DEGRADATION; STRUCTURE ANALYSIS;

EID: 17144429265     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (25)

1. DiSanto, A. R.; Wagner, J. G., J. Pharm. Sci., 1972, 61, 598.
2. DiSanto, A. R.; Wagner, J. G., J. Pharm. Sci., 1972, 61, 1086.
3. DiSanto, A. R.; Wagner, J. G., J. Pharm. Sci., 1972, 61, 1090.
4. Gurr, E., 'Staining-Practical and Theoretical' 2nd Edition, Williams and Watkins, Baltimore, Md., 1962, pp 303.
5. Wischik, C. M., WO 96/30766 Filing date 25.03.96.
6. Dreser, H., Z. Biol., 1885, 21, 41.
7. Muller, F., Deut. Arch. Klin. Med., 1899, 53, 130.
8. Elsner, K., Deut. Arch. Klin. Med., 1901, 59, 47.
9. Herter, P., Am. J. Physiol., 1904, 12, 128.
10. Underbill, F.; Closson, O., Am. J. Physiol., 1905, 13, 358.
11. Griffiths, R., Prog. in Neurobiol., 1990, 35, 313.
12. Methylene blue is an antidote to both cyanide and nitrate poisoning, The Merck Index, 11th edition, pp 5979. It presumably acts by anion binding followed by excretion.
13. Breslow, R., Chem. Ind. (London), 1956, R28.
14. The central nitrogen of methylene blue can be acetylated by treatment with zinc dust then acetic anhydride. Obata, H., B. Chem. Soc. Jap., 1961, 34, 1057; Cohn, G., Ber., 1900, 33, 1567.
15. The central nitrogen of methylene blue can be acetylated by treatment with zinc dust then acetic anhydride. Obata, H., B. Chem. Soc. Jap., 1961, 34, 1057; Cohn, G., Ber., 1900, 33, 1567.
16. The author has observed by TLC the formation of methylene violet as the major degradation product of MB with alkali (see ref. 16)
17. For some early studies on the oxidation and hydrolysis of methylene blue see Bernthsen, A., Ber., 1906, 1804; Bernthsen, A., Annalen, 1885, 230, 169 and 211; Conn's, H. J., Biological Stains, ed. Lillie, R. D., Pub. Williams and Wilkins, Baltimore, 9th edition, 1977, pp 493-502.
18. For some early studies on the oxidation and hydrolysis of methylene blue see Bernthsen, A., Ber., 1906, 1804; Bernthsen, A., Annalen, 1885, 230, 169 and 211; Conn's, H. J., Biological Stains, ed. Lillie, R. D., Pub. Williams and Wilkins, Baltimore, 9th edition, 1977, pp 493-502.
19. For some early studies on the oxidation and hydrolysis of methylene blue see Bernthsen, A., Ber., 1906, 1804; Bernthsen, A., Annalen, 1885, 230, 169 and 211; Conn's, H. J., Biological Stains, ed. Lillie, R. D., Pub. Williams and Wilkins, Baltimore, 9th edition, 1977, pp 493-502.
20. 1H NMR spectrum was apparent.
21. 3, Merck Index, 11th edition, pp 1358.
22. Rzepa, H., personal communication.
23. Hosoya, S., Acta Cryst. 1963, 16, 310.
24. Treatment of MB with bleach (12% w/v chlorine) then alkali gives a slightly more polar but weaker red spot by TLC analysis characteristic of the chlorine analogue of 4. Treatment of MB with I-Cl then alkali gave no red product.
25. Olszowy, H. A., J. Anal. Tox., 1998, 22, 225.