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Chemistry

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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

Nitrilotriacetic Acid
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

Nitrilotriacetic Acid

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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API | Excipient name

Nitrilotriacetic Acid

Synonyms

139-13-9, 2,2',2''-nitrilotriacetic acid, Triglycollamic acid, N,n-bis(carboxymethyl)glycine, Aminotriacetic acid, Complexon i

Cas Number

139-13-9

Unique Ingredient Identifier (UNII)

KA90006V9D

About Nitrilotriacetic Acid

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.)

Nitrilotriacetic Acid Manufacturers

A Nitrilotriacetic Acid manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Nitrilotriacetic Acid, including repackagers and relabelers. The FDA regulates Nitrilotriacetic Acid manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Nitrilotriacetic Acid API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

Nitrilotriacetic Acid Suppliers

A Nitrilotriacetic Acid supplier is an individual or a company that provides Nitrilotriacetic Acid active pharmaceutical ingredient (API) or Nitrilotriacetic Acid finished formulations upon request. The Nitrilotriacetic Acid suppliers may include Nitrilotriacetic Acid API manufacturers, exporters, distributors and traders.

Nitrilotriacetic Acid GMP

Nitrilotriacetic Acid Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Nitrilotriacetic Acid GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Nitrilotriacetic Acid GMP manufacturer or Nitrilotriacetic Acid GMP API supplier for your needs.

Nitrilotriacetic Acid CoA

A Nitrilotriacetic Acid CoA (Certificate of Analysis) is a formal document that attests to Nitrilotriacetic Acid's compliance with Nitrilotriacetic Acid specifications and serves as a tool for batch-level quality control.

Nitrilotriacetic Acid CoA mostly includes findings from lab analyses of a specific batch. For each Nitrilotriacetic Acid CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Nitrilotriacetic Acid may be tested according to a variety of international standards, such as European Pharmacopoeia (Nitrilotriacetic Acid EP), Nitrilotriacetic Acid JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Nitrilotriacetic Acid USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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