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Chemistry

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Also known as: 1,3,5-triazine-2,4,6-triamine, 108-78-1, Cyanuramide, Cyanurotriamide, Cyanurotriamine, Isomelamine
Molecular Formula
C3H6N6
Molecular Weight
126.12  g/mol
InChI Key
JDSHMPZPIAZGSV-UHFFFAOYSA-N
FDA UNII
N3GP2YSD88

Melamine
melamine is a natural product found in Euglena gracilis, Aeromonas veronii, and Apis cerana with data available.
1 2D Structure

Melamine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
1,3,5-triazine-2,4,6-triamine
2.1.2 InChI
InChI=1S/C3H6N6/c4-1-7-2(5)9-3(6)8-1/h(H6,4,5,6,7,8,9)
2.1.3 InChI Key
JDSHMPZPIAZGSV-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1(=NC(=NC(=N1)N)N)N
2.2 Other Identifiers
2.2.1 UNII
N3GP2YSD88
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1,3,5-triazine-2,4,6-triamine

2. 2,4,6-triamino-s-triazine

3. Melamine Bis(oxymethyl)phosphonic Acid Salt

4. Melamine Oxalate (1:1)

5. Melamine Phosphate

6. Melamine Sulfate (1:1)

7. Melamine Sulfate (1:2)

8. Melamine Sulfate (2:1), Dihydrate

9. Melamine Sulfate (4:1), Tetrahydrate

10. Melamine Sulfite (1:1)

11. Melamine Sulfite (2:1), Dihydrate

12. Melamine Sulfite (2:1), Tetrahydrate

13. Melaminium Acetate Acetic Acid Solvate

14. Melaminium Citrate

2.3.2 Depositor-Supplied Synonyms

1. 1,3,5-triazine-2,4,6-triamine

2. 108-78-1

3. Cyanuramide

4. Cyanurotriamide

5. Cyanurotriamine

6. Isomelamine

7. Theoharn

8. Teoharn

9. Triaminotriazine

10. Cyanuric Triamide

11. Hicophor Pr

12. S-triazinetriamine

13. Aero

14. 2,4,6-triamino-s-triazine

15. Yukamelamine

16. Pluragard

17. Cymel

18. 2,4,6-triamino-1,3,5-triazine

19. Virset 656-4

20. Spinflam Ml 94m

21. 2,4,6-triaminotriazine

22. Pluragard C 133

23. Adk Stab Zs 27

24. Mark Zs 27

25. Dg 002 (amine)

26. Melamine Monomer

27. Nci-c50715

28. Cyanurtriamide

29. S-triazine, 2,4,6-triamino-

30. 1,3,5-triazine-2,4,6(1h,3h,5h)-triimine

31. Zs 27

32. Nsc 2130

33. Dg 002

34. Sym-triaminotriazine

35. Dtxsid6020802

36. 1246816-14-7

37. N3gp2ysd88

38. Chebi:27915

39. Melamine 100 Microg/ml In Water

40. Nsc-2130

41. 1,3,5-triazine-2,4,6-triamine (melamine)

42. Melamine 100 Microg/ml In Acetonitrile/water

43. Melamine-13c3,15n3

44. Melamin

45. S-triaminotriazine

46. Ccris 373

47. Hsdb 2648

48. Einecs 203-615-4

49. Unii-n3gp2ysd88

50. Brn 0124341

51. 2,4,6-triamino Sym-triazine

52. Ai3-14883

53. Ax2

54. Melamine, 99%

55. 2,6-triaminotriazine

56. Cymel (salt/mix)

57. Melamine [hsdb]

58. Melamine [iarc]

59. Melamine [inci]

60. Metformin Ep Impurity D

61. 2,4,6-triamino-1,3,5-triazine Monomer

62. Melamine [mi]

63. Dsstox_cid_802

64. 2,6-triamino-s-triazine

65. Melamine [usp-rs]

66. 1,3,5-triazine-2,4,6(1h,3h,5h)triimine

67. Ec 203-615-4

68. S-triazine,4,6-triamino-

69. Dsstox_rid_75795

70. Dsstox_gsid_20802

71. Schembl25853

72. Melamine, Analytical Standard

73. 4-26-00-01253 (beilstein Handbook Reference)

74. 5432-64-4

75. Bidd:er0287

76. Chembl1231106

77. Schembl12192199

78. 1,5-triazine-2,4,6-triamine

79. 2,6-triamino-1,3,5-triazine

80. Nsc2130

81. Nsc8152

82. Zinc897751

83. Hy-y1117

84. Nsc-8152

85. Wln: T6n Cn Enj Bz Dz Fz

86. Tox21_200503

87. 1,3,5-triazinane-2,4,6-triimine

88. Bbl000010

89. Melamine 100 Microg/ml In Methanol

90. Mfcd00006055

91. S9212

92. Stk378738

93. [1,3,5]triazine-2,4,6-triamine

94. 1,3, 5-triazine-2,4,6-triamine

95. 2,4, 6-triamino-1,3,5-triazine

96. Akos005448714

97. Ccg-266105

98. Ncgc00164014-01

99. Ncgc00164014-02

100. Ncgc00258057-01

101. 2,4,6-triamino-1,3,5-triazine;melamine;1,3,5-triazine-2,4,6-triamine;[1,3,5]triazine-2,4,6-triamine;s-triazine, 4,6-diamino-1,2-dihydro-2-imino-;2,4,6-triamino-1,3,5-triazine Melamine 1,3,5-triazine-2,4,6-triamine [1,3,5]triazine-2,4,6-triamine S-triazine, 4,6-diamino-1,2-dihydro-2-imino-

102. Ac-34715

103. Cas-108-78-1

104. Vs-00405

105. 1,3,5-triazine-2,4,6-triamine Monomer

106. Melamine 1.0 Mg/ml In Dimethyl Sulfoxide

107. Cs-0016866

108. Ft-0609833

109. Ft-0670982

110. Ft-0670983

111. Melamine; 1,3,5-triazine-2,4,6-triamine

112. T0337

113. 1,5-triazine-2,4,6(1h,3h,5h)-triimine

114. 4,6-diamino-1,2-dihydro-2-imino-s-triazine

115. C08737

116. E76265

117. S-triazine, 4,6-diamino-1,2-dihydro-2-imino-

118. Q212553

119. J-002191

120. 1,3,5-triazine-2,4,6-triamine (acd/name 4.0)

121. 2,4,6-triamino-1,3,5-triazine, Sym-triaminotriazine

122. Metformin Hydrochloride Impurity D [ep Impurity]

123. Melamine, >=95.0% (hplc), Pharmaceutical Impurity Standard

124. Melamine, United States Pharmacopeia (usp) Reference Standard

125. N,n',n''-tri-2-pyridinyl-1,3,5-triazine-2,4,6-triamine

126. Melamine, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 126.12 g/mol
Molecular Formula C3H6N6
XLogP3-1.4
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count0
Exact Mass126.06539422 g/mol
Monoisotopic Mass126.06539422 g/mol
Topological Polar Surface Area117 Ų
Heavy Atom Count9
Formal Charge0
Complexity63.3
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 Absorption, Distribution and Excretion

... A single oral dose of 0.025 mCi (0.38 mg) [14C]melamine /was administered/ to adult male Fischer 344 rats. Within the first 24 hr, 90% of the administered dose was excreted in the urine. Negligible radioactivity appeared in breath and feces. There was little difference in blood, liver or plasma concentrations of 14C, suggesting that melamine distributes in body water. The only organs showing radioactivity levels much higher than plasma were the kidney and bladder. The bladder level was by far the highest, a finding probably due either to back diffusion from urine or to contamination of bladder tissue with urine. Virtually no residual radioactivity was observed in tissues examined at 24 hr or later. The elimination-phase half-life calculated from plasma data, 2.7 hr, was in good agreement with the urinary-excretion half-life of 3.0 hr. The renal clearance of melamine was 2.5 mL/min.

PMID:6686586 Mast RW et al; Food Chem Toxicol 21 (6): 807-10 (1983)


... Following oral administration of 250 mg/kg melamine to rats, 50% of the mother compound was excreted with the urine within 6 hrs. ... Crystals found in the urine were composed of dimelamine monophosphate, amounting to nearly 20% of the administered dose. After feeding melamine to dogs, 60 - 86.5% of the mother compound was recovered in the urine within 24 hrs. ...

European Chemicals Bureau; IUCLID Dataset, Melamine (CAS # 108-78-1) p.79 Available from, as of June 26, 2007: https://esis.jrc.ec.europa.eu/


Doses of 2.4 g/kg cause diuresis & elimination of fine crystals of dimelamine monophosphate in urine.

Lefaux, R. Practical Toxicology of Plastics. Cleveland: CRC Press Inc., 1968., p. 330


After administration of a single oral dose of 0.38 mg (14)C-melamine to adult male Fischer 344/N rats, 90% of the administered dose was excreted in the urine within the first 24 hours. Negligible radioactivity was detected in exhaled air and feces; and radioactivity was concentrated in the kidney and bladder. Virtually no residual radioactivity was observed in tissue after 24 hours or more. Chromatography of the radioactivity found in plasma or urine indicated that melamine is not metabolized in rats.

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. V39 340 (1986)


4.2 Metabolism/Metabolites

Toxicokinetic studies in rats given 14C-labelled cyromazine as single and repeated oral doses showed that the active substance is rapidly and almost completely absorbed from the gastrointestinal tract and distributed to all organs and tissues. ... Cyromazine was incompletely metabolized, essentially by methylation, hydroxylation or Ndealkylation. The major component present was cyromazine, which accounted for 71-72% of the radiolabel; a further 7% was attributable to melamine, 8-11% to hydroxy-cyromazine and methylcyromazine.

Joint FAO/WHO Meeting on Pesticide Residues in Food. FAO Plant Production and Protection Paper 187; Cyromazine p.102 (October 2006) Available from: https://www.fao.org/ag/agp/agpp/Pesticid/Default.htm


... A single oral dose of 0.025 mCi (0.38 mg) [14C]melamine /was administered/ to adult male Fischer 344 rats. ... Radioactivity in plasma or urine co-chromatographed with that of the dosing solution, indicating that melamine is not metabolized in the male Fischer 344 rat.

PMID:6686586 Mast RW et al; Food Chem Toxicol 21 (6): 807-10 (1983)


Crystalluria was due to excretion of dimelamine-monophosphate crystals.

Bingham, E.; Cohrssen, B.; Powell, C.H.; Patty's Toxicology Volumes 1-9 5th ed. John Wiley & Sons. New York, N.Y. (2001)., p. 4:1335


4.3 Biological Half-Life

... A single oral dose of 0.025 mCi (0.38 mg) [14C]melamine /was administered/ to adult male Fischer 344 rats. ... The elimination-phase half-life calculated from plasma data, 2.7 hr, was in good agreement with the urinary-excretion half-life of 3.0 hr. ...

PMID:6686586 Mast RW et al; Food Chem Toxicol 21 (6): 807-10 (1983)


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