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Chemistry

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Also known as: Direct blue 14, 72-57-1, C.i. direct blue 14, Niagara blue, Visionblue, Benzamine blue
Molecular Formula
C34H24N6Na4O14S4
Molecular Weight
960.8  g/mol
InChI Key
GLNADSQYFUSGOU-UHFFFAOYSA-J
FDA UNII
I2ZWO3LS3M

Trypan Blue
A diazo-naphthalene sulfonate that is widely used as a stain.
1 2D Structure

Trypan Blue

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
tetrasodium;5-amino-3-[[4-[4-[(8-amino-1-hydroxy-3,6-disulfonatonaphthalen-2-yl)diazenyl]-3-methylphenyl]-2-methylphenyl]diazenyl]-4-hydroxynaphthalene-2,7-disulfonate
2.1.2 InChI
InChI=1S/C34H28N6O14S4.4Na/c1-15-7-17(3-5-25(15)37-39-31-27(57(49,50)51)11-19-9-21(55(43,44)45)13-23(35)29(19)33(31)41)18-4-6-26(16(2)8-18)38-40-32-28(58(52,53)54)12-20-10-22(56(46,47)48)14-24(36)30(20)34(32)42;;;;/h3-14,41-42H,35-36H2,1-2H3,(H,43,44,45)(H,46,47,48)(H,49,50,51)(H,52,53,54);;;;/q;4*+1/p-4
2.1.3 InChI Key
GLNADSQYFUSGOU-UHFFFAOYSA-J
2.1.4 Canonical SMILES
CC1=C(C=CC(=C1)C2=CC(=C(C=C2)N=NC3=C(C4=C(C=C(C=C4C=C3S(=O)(=O)[O-])S(=O)(=O)[O-])N)O)C)N=NC5=C(C6=C(C=C(C=C6C=C5S(=O)(=O)[O-])S(=O)(=O)[O-])N)O.[Na+].[Na+].[Na+].[Na+]
2.2 Other Identifiers
2.2.1 UNII
I2ZWO3LS3M
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Blue, Diamine

2. Blue, Niagara

3. Blue, Trypan

4. Diamine Blue

5. Niagara Blue

6. Visionblue

2.3.2 Depositor-Supplied Synonyms

1. Direct Blue 14

2. 72-57-1

3. C.i. Direct Blue 14

4. Niagara Blue

5. Visionblue

6. Benzamine Blue

7. Dianil Blue

8. Diamine Blue

9. Benzo Blue

10. Congo Blue

11. Naphthylamine Blue

12. Diphenyl Blue

13. C.i. 23850

14. Niagara Blue 3b

15. Trypan-blue

16. Diamineblue

17. Dianilblau

18. Pyrotropblau

19. Parkibleu

20. Parkipan

21. Bleu Diamine

22. Chloramine Blue

23. Trypane Blue

24. Tripan Blue

25. Benzaminblau 3b

26. Chloramiblau 3b

27. Bleu Trypane N

28. Benzanil Blue R

29. Diaminblau 3b

30. Directblau 3b

31. Triazolblau 3bx

32. Benzoblau 3b

33. Congoblau 3b

34. Dianilblau H3g

35. Renolblau 3b

36. Bleu Directe 3b

37. Azidine Blue 3b

38. Diamine Blue 3b

39. Diazine Blue 3b

40. Pyrazol Blue 3b

41. Trypan Blue Bpc

42. Bleue Diretto 3b

43. Bencidal Blue 3b

44. Dianil Blue H3g

45. Diazol Blue 3b

46. Diphenyl Blue 3b

47. Direct Blue 3b

48. Direct Blue 3bx

49. Direct Blue D3b

50. Direct Blue H3g

51. Direct Blue M3b

52. Paramine Blue 3b

53. Azurro Diretto 3b

54. Benzo Blue 3b

55. Benzo Blue 3bs

56. Blue Emb

57. Naphthaminblau 3bx

58. Orion Blue 3b

59. Benzamine Blue 3b

60. Chlorazol Blue 3b

61. Cresotine Blue 3b

62. Amanil Sky Blue R

63. Benzanil Blue 3bn

64. Centraline Blue 3b

65. Chloramine Blue 3b

66. Hispamin Blue 3bx

67. I2zwo3ls3m

68. Diaphtamine Blue Th

69. Bleu Diazole N 3b

70. Blue 3b

71. Pontamine Blue 3bx

72. Brasilamina Blue 3b

73. Brasilazina Blue 3b

74. Directakol Blue 3bl

75. Naphthamine Blue 3bx

76. C.i. Direct Blue 14, Tetrasodium Salt

77. Chrome Leather Blue 3b

78. Trianol Direct Blue 3b

79. Sodium Ditolyl-diazobis-8-amino-1-naphthol-3,6-disulfonate

80. Chebi:78897

81. Trypanblau

82. Nsc-11247

83. Sodium Ditolyldisazobis-8-amino-1-naphthol-3,6-disulfonate

84. Sodium Ditolyldisazobis-8-amino-1-naphthol-3,6-disulphonate

85. Diaminine Blue

86. Vision Blue

87. Azidinblau 3b

88. Directblue14

89. Trypanblau [german]

90. Trypan (congo) Blue

91. Modr Trypanova [czech]

92. Ncgc00167554-01

93. Modr Prima 14 [czech]

94. Rcra Waste No. U236

95. Rcra Waste Number U236

96. Membraneblue

97. Ccris 616

98. Azul Tripano

99. Bleu Trypan

100. Modr Trypanova

101. Trypan Blue (commercial Grade)

102. Hsdb 2945

103. Nci C61289

104. Einecs 200-786-7

105. Modr Prima 14

106. Mfcd00003969

107. Nsc 11247

108. Trypan Blue Solution

109. Ai3-26698

110. 2,7-naphthalenedisulfonic Acid,3,3'-[(3,3'-dimethyl[1,1'-biphenyl]-4,4'-diyl)bis(azo)]bis[5-amino-4-hydroxy-, Tetrasodium Salt

111. Unii-i2zwo3ls3m

112. Dsstox_cid_6268

113. Trypan Blue [mi]

114. Trypan Blue [hsdb]

115. Trypan Blue [iarc]

116. Chembl1640

117. Dsstox_rid_78083

118. Trypan Blue [vandf]

119. Dsstox_gsid_26268

120. Trypan Blue [mart.]

121. Trypan Blue [who-dd]

122. Chembl177987

123. Trypan Blue, Dye Content 60%

124. Dtxsid4026268

125. Trypan Blue [orange Book]

126. Amy22430

127. Tox21_112549

128. Akos015902434

129. Akos030228627

130. Cas-72-57-1

131. 2,7-naphthalenedisulfonic Acid, 3,3'-((3,3'-dimethyl(1,1'-biphenyl)-4,4'-diyl)bis(azo))bis(5-amino-4-hydroxy-, Tetrasodium Salt

132. As-83614

133. Tetrasodium 3,3'-((3,3'-dimethyl(1,1'-biphenyl)-4,4'-diyl)bis(azo))bis(5-amino-4-hydroxynaphthalene-2,7-disulphonate)

134. Ft-0690008

135. T0556

136. C19307

137. Sodium Ditolyl-diazobis-8-amino-1-naphthol-3,6-disulphonate

138. 2,7-naphthalenedisulfonic Acid, 3,3'-((3,3'-dimethyl(1,1'-biphenyl)-4,4'-diyl)bis(2,1-diazenediyl))bis(5-amino-4-hydroxy-, Sodium Salt (1:4)

139. 3,3'-((3,3'-dimethyl(1,1'-biphenyl)-4,4'-diyl)bis(azo))bis-(5-amino-4-hydroxy)-2,7-naphthalenedisulfonic Acid Tetrasodium Salt

140. 3,3'-((3,3'-dimethyl-4,4'-biphenylene)bis(azo))bis(5-amino-4-hydroxy-2,7-naphthalenedisulfonic Acid) Tetrasodium Salt

141. Sodium 3,3'-(1e,1'e)-(3,3'-dimethylbiphenyl-4,4'-diyl)bis(diazene-2,1-diyl)bis(5-amino-4-hydroxynaphthalene-2,7-disulfonate)

142. Tetrasodium 3,3'-((3,3'-dimethyl(1,1'-biphenyl)-4,4'-diyl)bis(azo))bis(5-amino-4-hydroxynaphthalene-2,7-disulphonate

143. Tetrasodium 3,3'-((3,3'-dimethyl-4,4'-biphenylene)bis(azo))bis(5-amino-4-hydroxy-2,7-naphthalenedisulfonate)

144. Tetrasodium 3,3'-((3,3'-dimethyl-4,4'-biphenylene)bis(azo))bis(5-amino-4-hydroxy-2,7-naphthalenedisulphonate)

145. Tetrasodium 3,3'-[(3,3'-dimethylbiphenyl-4,4'-diyl)didiazene-2,1-diyl]bis(5-amino-4-hydroxynaphthalene-2,7-disulfonate)

2.4 Create Date
2005-07-19
3 Chemical and Physical Properties
Molecular Weight 960.8 g/mol
Molecular Formula C34H24N6Na4O14S4
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count20
Rotatable Bond Count5
Exact Mass959.9824113 g/mol
Monoisotopic Mass959.9824113 g/mol
Topological Polar Surface Area404 Ų
Heavy Atom Count62
Formal Charge0
Complexity1790
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count5
4 Drug and Medication Information
4.1 Therapeutic Uses

A diazo-naphthalene sulfonate that is widely used as a stain.

NLM; Medical Subject Headings (2010 MeSH) for trypan blue, RN 72-57-1. Available from, as of June 17, 2010: https://www.nlm.nih.gov/cgi/mesh/2010/MB_cgi?term=72-57-1&rn=1


A therapeutic agent in the treatment of sleeping sickness. /Former use/

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V8 269 (1975)


MembraneBlue 0.15% is indicated for use as an aid in ophthalmic surgery by staining the epiretinal membranes during ophthalmic surgical vitrectomy procedures, facilitating removal of the tissue.

US Natl Inst Health; DailyMed. Current Medication Information for MEMBRANEBLUE (trypan blue) injection, solution (March 2010). Available from, as of June 28, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=15868


/Experimental Therapy/ Trypan blue can be used to stain the superior oblique tendon for easy identification and delineation of it at its insertion, making the current surgical technique less difficult.

PMID:17274335 Saxena R et al; J Pediatr Opthalmol Strabusmus 44 (1): 45-6 (2007)


For more Therapeutic Uses (Complete) data for Trypan blue (6 total), please visit the HSDB record page.


4.2 Drug Warning

Adverse reactions reported following use of VisionBlue include discoloration of high water content hydrogen intraocular lenses (see Contraindications) and inadvertent staining of the posterior lens capsule and vitreous face. Staining of the posterior lens capsule or staining of the vitreous face is generally self limited, lasting up to one week.

US Natl Inst Health; DailyMed. Current Medication Information for VISIONBLUE (trypan blue) injection, solution (March 2006). Available from, as of June 28, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=15897


It is not known whether this drug is excreted in human milk. Because many drugs are excreted in human milk, caution should be exercised when trypan blue is administered to a nursing woman.

US Natl Inst Health; DailyMed. Current Medication Information for VISIONBLUE (trypan blue) injection, solution (March 2006). Available from, as of June 28, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=15897


VisionBlue is contraindicated when a non-hydrated (dry state), hydrophilic acrylic intraocular lens is planned to be inserted into the eye because the dye may be absorbed by the intraocular lens and stain theintraocular lens.

US Natl Inst Health; DailyMed. Current Medication Information for VISIONBLUE (trypan blue) injection, solution (March 2006). Available from, as of June 28, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=15897


It is recommended that after injection all excess VisionBlue be immediately removed from the eye by thorough irrigation of the anterior chamber.

US Natl Inst Health; DailyMed. Current Medication Information for VISIONBLUE (trypan blue) injection, solution (March 2006). Available from, as of June 28, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=15897


FDA Pregnancy Risk Category: C /RISK CANNOT BE RULED OUT. Adequate, well controlled human studies are lacking, and animal studies have shown risk to the fetus or are lacking as well. There is a chance of fetal harm if the drug is given during pregnancy; but the potential benefits may outweigh the potential risk./

US Natl Inst Health; DailyMed. Current Medication Information for VISIONBLUE (trypan blue) injection, solution (March 2006). Available from, as of June 28, 2010: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=15897


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Coloring Agents

Chemicals and substances that impart color including soluble dyes and insoluble pigments. They are used in INKS; PAINTS; and as INDICATORS AND REAGENTS. (See all compounds classified as Coloring Agents.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Dyes [MoA]; Diagnostic Dye [EPC]
5.3 Absorption, Distribution and Excretion

Trypan blue ... was observed in animals to pass from bloodstream through walls of vessels of iris & choroid, but not through walls of retinal vessels.

Grant, W.M. Toxicology of the Eye. 3rd ed. Springfield, IL: Charles C. Thomas Publisher, 1986., p. 959


Following sc or ip injections into mice or rats, trypan blue is rapidly absorbed & widely distributed throughout the body. Max serum concentrations are ... within 2 hr; it appears bound to serum proteins with ... rapid excretion in urine & uptake by the reticulo-endothelial system.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V8 272 (1973)


Trypan blue never reaches the rat embryo, but accumulates in maternal reticuloendothelial system and in the placenta.

Doull, J., C.D. Klaassen, and M. D. Amdur (eds.). Casarett and Doull's Toxicology. 2nd ed. New York: Macmillan Publishing Co., 1980., p. 168


Experiments with ring-labelled radioactive trypan blue did not give evidence of any embryonic incorporation of the (14)C. The absence of teratogenic action after the initiation of chorio-allantoic placentation also indicated that yolk sac function was important in pathogenesis. The dye can be visualized in the cells of the visceral yolk sac.

Shepard, T.H. Catalog of Teratogenic Agents. 5th ed. Baltimore, MD: The Johns Hopkins University Press, 1986., p. 584


For more Absorption, Distribution and Excretion (Complete) data for Trypan blue (6 total), please visit the HSDB record page.


5.4 Metabolism/Metabolites

/Trypan blue/ is reduced in vitro by a rat liver enzyme to ortho-tolidine & 2,8-diamino-1-naphthol-3,6-disulfonic acid.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V8 273 (1975)


Six azo dyes, including trypan blue, were reduced, N-acetylated, and N-conjugated. No N,N'-diacetylated metabolites were detected in rat urine.

KENNALLY JC ET AL; CARCINOGENESIS (LONDON) 3 (8): 947 (1982)


Azo dyes based on beta-diketone coupling components exist preferentially as the tautomeric hydrazones. A series of hydrazone dyes based on benzidine and benzidine congeners ... was prepared. The hydrazone dyes were resistant to enzymatic reduction by FMN supplemented hamster liver post-mitochondrial supernatant (S-9); under identical conditions, azo dyes such as trypan blue were rapidly reduced.

PMID:3957165 De France BF et al; Food Chem Toxicol 24 (2): 165-9 (1986)


Metabolism experiments were conducted with rats dosed with 9 azo dyes based on dimethyl-, dimethoxy-, or dichlorobenzidine to determine whether the free amine congeners, their monoacetyl or diacetyl metabolites, or alkaline hydrolyzable conjugates were excreted in the urine. 2-mg doses were administered and urine samples were collected at intervals up to 96 hr. Peak levels of metabolites were excreted either 0-12 or 12-24 hr after administration and, in 7 of 9 instances, no metabolites persisted in the urine after 48 hr. Minimum detectable levels of all metabolites were 12 ppb or less. All 9 dyes were converted to measurable levels of their benzidine-congener-based metabolites in rats.

PMID:6834800 Bowman MC et al; J Anal Toxicol 7 (l): 55-60 (1983)


The ability of rat liver microsomes from phenobarbitone pretreated animals to reduce the azo groups of amaranth, sunset yellow, congo red, trypan blue, chloramine sky blue FF and direct black 38 was measured in vitro. The dyes amaranth and sunset yellow acted as positive controls. Of the dyes derived from (the carcinogen) benzidine or its congeners, only direct black 38 was reduced to an appreciable extent; the rate of reduction was 10% of that for amaranth. The dyes were tested for mutagenicity in the Salmonella/microsome assay, the only active compound being direct black 38. Mutagenicity of this dye may be due in part to the mutagen 1,2,4-triaminobenzene. Mutagenic activity and azo-reduction of direct black 38 was independent of the presence of oxygen. Mammalian liver may play only a minor or negligible role in the azo-reduction of dyes derived from benzidine or its congeners.

Martin CN, Kennelly JC; Carcinogenesis (Lond) 2 (4): 307-12 (1981)


5.5 Mechanism of Action

A dose of 50 mg per kg /of trypan blue/ appears to be the optimum teratogenic dose. A characteristic observation with trypan blue is that with treatment after the 9th day of gestation defects are rare. This fact has supported other evidence that the mechanism of action was dependent on disruption of yolk sac nutrition. ... Studies have produced evidence indicating a possible action of trypan blue on a nutritive function of the visceral yolk sac. The failure of the trypan blue to act directly upon the embryo is generally held ... .

Shepard, T.H. Catalog of Teratogenic Agents. 5th ed. Baltimore, MD: The Johns Hopkins University Press, 1986., p. 584


The absence of teratogenic action after the initiation of chorio-allantoic placentation also indicated that yolk sac function was important in pathogenesis. The dye can be visualized in the cells of the visceral yolk sac. ... . The protein-trypan blue complex is concentrated in lysosomes. Through disruption of the enzymatic digestive process in the yolk sac lysosome, trypan blue may interfere with normal embryonic nutritive processes.

Shepard, T.H. Catalog of Teratogenic Agents. 5th ed. Baltimore, MD: The Johns Hopkins University Press, 1986., p. 584


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26-Feb-2024
26-Feb-2024
KGS
overview
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Average Price (USD/KGS)

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country Total Quantity
(KGS)
Average Price
(USD/KGS)
Number of Transactions

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