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MolPort-001-792-516
Also known as: 139-13-9, 2,2',2''-nitrilotriacetic acid, Triglycollamic acid, N,n-bis(carboxymethyl)glycine, Aminotriacetic acid, Complexon i
Molecular Formula
C6H9NO6
Molecular Weight
191.14  g/mol
InChI Key
MGFYIUFZLHCRTH-UHFFFAOYSA-N
FDA UNII
KA90006V9D

A derivative of acetic acid, N(CH2COOH)3. It is a complexing (sequestering) agent that forms stable complexes with Zn2+. (From Miall's Dictionary of Chemistry, 5th ed.)
1 2D Structure

MolPort-001-792-516

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[bis(carboxymethyl)amino]acetic acid
2.1.2 InChI
InChI=1S/C6H9NO6/c8-4(9)1-7(2-5(10)11)3-6(12)13/h1-3H2,(H,8,9)(H,10,11)(H,12,13)
2.1.3 InChI Key
MGFYIUFZLHCRTH-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C(C(=O)O)N(CC(=O)O)CC(=O)O
2.2 Other Identifiers
2.2.1 UNII
KA90006V9D
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Acid, Nitrilotriacetic

2. Aluminum Nitrilotriacetate

3. Dysprosium Nitrilotriacetate

4. Nitrilotriacetate, Aluminum

5. Nitrilotriacetate, Dysprosium

6. Nitrilotriacetate, Trisodium

7. Trisodium Nitrilotriacetate

2.3.2 Depositor-Supplied Synonyms

1. 139-13-9

2. 2,2',2''-nitrilotriacetic Acid

3. Triglycollamic Acid

4. N,n-bis(carboxymethyl)glycine

5. Aminotriacetic Acid

6. Complexon I

7. Nta

8. Nitrilotriacetate

9. Trilon A

10. Glycine, N,n-bis(carboxymethyl)-

11. 2-[bis(carboxymethyl)amino]acetic Acid

12. Komplexon I

13. Titriplex I

14. Versene Nta Acid

15. Nitrilotriessigsaeure

16. Hampshire Nta Acid

17. Tri(carboxymethyl)amine

18. Nitrilo-2,2',2''-triacetic Acid

19. Acetic Acid, Nitrilotri-

20. Nitrilotriaceticacid

21. 2-(bis(carboxymethyl)amino)acetic Acid

22. Chel 300

23. Nci-c02766

24. Mfcd00004287

25. Nitrilotriacetic Acid (nta)

26. Alpha,alpha',alpha''-trimethylaminetricarboxylic Acid

27. Chebi:44557

28. Ka90006v9d

29. Nsc-2121

30. Nitriloacetate

31. Dsstox_cid_939

32. Dsstox_rid_75878

33. Dsstox_gsid_20939

34. Tris(carboxymethyl)amine

35. Cas-139-13-9

36. Ccris 436

37. Aminotriethanoic Acid

38. N,n-bis(carboxymethyl)glysine

39. Hsdb 2853

40. Kyselina Nitrilotrioctova [czech]

41. Kyselina Nitrilotrioctova

42. Nsc 2121

43. Einecs 205-355-7

44. Brn 1710776

45. Unii-ka90006v9d

46. Ai3-52483

47. H3nta

48. Potassium Cadmium Nitrilotriacetate

49. Einecs 256-488-2

50. Nitrilotriacetic-acid

51. Wln: Qv1n1vq1vq

52. Ec 205-355-7

53. Cambridge Id 5122183

54. Nitrilotriessigsa Currencyure

55. N(ch2-cooh)3

56. Nta (nitrilotriacetic Acid)

57. Schembl20409

58. 4-04-00-02441 (beilstein Handbook Reference)

59. 80751-51-5

60. Mls000069464

61. Bidd:er0361

62. Glycine,n-bis(carboxymethyl)-

63. Nitrilo-2,2''-triacetic Acid

64. Chembl1234848

65. Dtxsid6020939

66. Nsc2121

67. Hms2232k17

68. Nitrilotriacetic Acid [mi]

69. Ccg-2133

70. Str02791

71. Zinc1849692

72. Nitrilotriacetic Acid [hsdb]

73. Nitrilotriacetic Acid, P.a., 99%

74. Tox21_202195

75. Tox21_300156

76. Bbl002469

77. Nitrilo-n,n,n-triacetic Acid

78. Stk387109

79. Akos005441655

80. Nitrilotriacetic Acid [usp-rs]

81. Db03040

82. Hy-w030778

83. Ncgc00091141-01

84. Ncgc00091141-02

85. Ncgc00091141-03

86. Ncgc00091141-04

87. Ncgc00254116-01

88. Ncgc00259744-01

89. Bp-30104

90. Cadmate(1-), (n,n-bis((carboxy-kappao)methyl)glycinato(3-)-kappan,kappao)-, Potassium (1:1), (t-4)-

91. Cadmate(1-), (n,n-bis((carboxy-kappao)methyl)glycinato(3-)-kappan,kappao)-, Potassium, (t-4)-

92. Smr000054748

93. 2-[bis(carboxymethyl)amino]essigsäure

94. Db-042463

95. Cs-0074802

96. Ft-0631809

97. N0098

98. Nitrilotriacetic Acid Acs Grade 100g

99. Nitrilotriacetic Acid, Sigma Grade, >=99%

100. Nitrilotriacetic Acid, Acs Reagent, >=99.0%

101. Nitrilotriacetic Acid, Bioultra, >=99.0% (t)

102. .alpha.,.alpha.''-trimethylaminetricarboxylic Acid

103. A,a',a''-trimethylaminetricarboxylic Acid

104. Disodium Edetate Impurity A [ep Impurity]

105. Nitrilotriacetic Acid And Its Salts [iarc]

106. Q425340

107. J-007239

108. F1905-6980

109. Sodium Calcium Edetate Impurity A [ep Impurity]

110. Z1889996324

111. Nitrilotriacetic Acid, Acs Reagent, For Complexometry, >=98%

112. Nitrilotriacetic Acid, United States Pharmacopeia (usp) Reference Standard

113. Potassium (n,n-bis(carboxymethyl)glycinato(3-)-n,o,o',o'')cadmate(1-)

114. Nitrilotriacetic Acid, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 191.14 g/mol
Molecular Formula C6H9NO6
XLogP3-3.2
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count7
Rotatable Bond Count6
Exact Mass191.04298701 g/mol
Monoisotopic Mass191.04298701 g/mol
Topological Polar Surface Area115 Ų
Heavy Atom Count13
Formal Charge0
Complexity187
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 MeSH Pharmacological Classification

Chelating Agents

Chemicals that bind to and remove ions from solutions. Many chelating agents function through the formation of COORDINATION COMPLEXES with METALS. (See all compounds classified as Chelating Agents.)


4.2 Absorption, Distribution and Excretion

AFTER ORAL ADMIN OF 180 MG/KG OR 45 MG/KG IV TO RATS, RELATIVELY HIGH CONCN OF NTA WERE FOUND IN LUNGS, INTESTINE, & MUSCLE. PATTERN OF DISTRIBUTION DEPENDED ON ROUTE OF ADMIN. APPROX 99% OF SINGLE ORAL DOSE ELIM IN 24 HR; 96% OF THIS WAS ELIM IN URINE.

CHU I ET AL; BULL ENVIRON CONTAM TOXICOL 19(4) 417 (1978)


NTA-(14)C ADMIN ORALLY TO RATS. 95% WAS EXCRETED IN URINE. LESS THAN 1% ... AS CO2. ABSORPTION OF NTA FROM GI TRACT VARIED: DOG GREATER THAN RAT GREATER THAN RABBIT & MONKEY ... DEPOSITED IN SKELETON. CONCN ... INCR WITH NUMBER OF ADMIN DOSES. MOST ACTIVE AREAS FOR ACCUMULATION ... @ SITES OF VERY ACTIVE BONE FORMATION. ALTHOUGH CONCN /NTA/ DECR RAPIDLY WITH CESSATION OF INTAKE, A SMALL AMT WAS RETAINED IN BONE AFTER EACH DOSE ... .

Menzie, C. M. Metabolism of Pesticides, An Update. U.S. Department of the Interior, Fish, Wild-life Service, Special Scientific Report - Wildlife No. 184, Washington, DC: U.S. Government Printing Office, l974., p. 279


DOGS ADMIN 10, 20, & 50 MG NITRILOTRIACETIC ACID/KG EXCRETED MATERIAL IDENTIFIED AS CHONDROITIN A SULFATE &/OR CHONDROITIN C SULFATE.

PMID:128847 JAQUES LB, SUE TK; TOXICOL APPL PHARMACOL 34 (3): 521 (1975)


The kidney attains concentrations of NTA greater than that in the plasma in rats with steady state plasma NTA levels. The relatively high kidney concentrations of NTA can be attributed to high concentrations of NTA in small volumes of urine. NTA is not metabolized in mammals and is excreted rapidly by filtration in the kidney ... .

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 198 (1989)


A capsule containing 10 mg [1 14C]NTA in gelatin was given orally in fruit juice to each of eight male volunteers who had received no drugs for two weeks before entering the study. Twelve % of the admin radioactivity was excreted in the urine & 77% in the feces as unchanged NTA within 120 h of admin. A peak in the blood concn (6.5 ng/g serum) occurred 12 h after dosing ... .

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 202 (1989)


4.3 Metabolism/Metabolites

WASHED CELL SUSPENSION OF PSEUDOMONAS SP, ISOLATED FROM SEWAGE EFFLUENT, DEGRADED ALL NTA-NITROGEN TO AMMONIUM PRIOR TO TOTAL CONVERSION OF NTA TO CO2 AND WATER. SMALL AMOUNT OF NITRITE WERE ALSO FORMED. STUDY TENDED TO SUPPORT CONTENTION THAT NTA DEGRADATION PROCEEDED THROUGH AMINODIACETIC ACID AND GLYCINE ... .

Menzie, C. M. Metabolism of Pesticides, An Update. U.S. Department of the Interior, Fish, Wild-life Service, Special Scientific Report - Wildlife No. 184, Washington, DC: U.S. Government Printing Office, l974., p. 279


In mammalian systems, NTA is not metabolized and is excreted rapidly by filtration in the kidney.

PMID:3899518 Anderson RL et al; Crit Rev Toxicol 15 (1): 1-102 (1985)


4.4 Mechanism of Action

A positive synergistic action was produced by nitrilotriacetic acid in combination with soluble chromium(VI) as potassium dichromate in the induction of gene mutations in Salmonella typhimurium and Drosophila melanogaster. The possibility that this action depended on an effect of nitrilotriacetic acid on chromium(VI) reduction by cellular proteins was demonstrated. Gene mutations were detected by the Ames plate incorporation test on strains (TA-100), (TA-92), (TA-104) and (TA-103) of Salmonella typhimurium. In both the Salmonella and Drosophila systems, the nitrilotriacetic acid synergistically increased the mutagenicity of subtoxic doses of chromium(VI) while at higher chromium(VI) dose levels a decline of mutation frequency was noted in the presence of nitrilotriacetic acid, probably as a result of toxicity. Both effects may be referred to enhanced availability of the final genotoxic agent in the presence of nitrilotriacetic acid. The interaction was particularly evident in strains (TA-100) and (TA-104) which carried mutations affecting cell wall permeability and DNA repair. In these strains, the uptake of chromium(VI) and nitrilotriacetic acid was increased and the resulting DNA damage repaired less efficiently or by error prone mechanisms. Nitrilotriacetic acid may facilitate chromate uptake by the anion carriers of the cell membrane. Other mechanisms linked to its chelating action may also be important as suggested by the significant synergistic effect on chromium(VI) mutagenicity produced by ethylenedinitrilotetraacetic acid at very low doses, which do not modify chromium(VI) reduction by Salmonella proteins in cell free conditions.

Gava C et al; Toxicol and Environ Chem 22 (1-4): 27-38 (1989)


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