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Nitrosamines

PubChem CID
37183
Structure
Nitrosamines_small.png
Nitrosamines_3D_Structure.png
Molecular Formula
Synonyms
  • Nitrosamine
  • Nitrosamide
  • nitrous amide
  • 35576-91-1
  • LGB75A6POH
Molecular Weight
46.029 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2005-03-26
  • Modify:
    2024-12-14
Description
Nitrosamine has been reported in Nicotiana tabacum with data available.
Nitrosamine is any of a class of organic compounds with the general formula R2NNO or RNHNO, present in various foods and other products and found to be carcinogenic in laboratory animals. (dictionary.com)
A class of compounds that contain a -NH2 and a -NO radical. Many members of this group have carcinogenic and mutagenic properties.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Nitrosamines.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

nitrous amide
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/H2N2O/c1-2-3/h(H2,1,3)
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

XKLJHFLUAHKGGU-UHFFFAOYSA-N
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.4 SMILES

NN=O
Computed by OEChem 2.3.0 (PubChem release 2024.11.20)

2.2 Molecular Formula

H2N2O
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 UNII

2.3.3 DSSTox Substance ID

2.3.4 NCI Thesaurus Code

2.3.5 Nikkaji Number

2.3.6 NSC Number

2.3.7 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Nitrosamine
  • Nitrosamines

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
46.029 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
Property Value
-0.6
Reference
Computed by XLogP3 3.0 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Hydrogen Bond Acceptor Count
Property Value
3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
46.016712692 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
46.016712692 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
55.5Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
3
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
10.3
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 SpringerMaterials Properties

3.3 Chemical Classes

Nitrogen Compounds -> Nitrosamines

5 Chemical Vendors

6 Use and Manufacturing

6.1 Uses

Sources/Uses
Nitrosamines are produced in foundry, tanning, and rubber manufacturing processes. Nitrosamines are carcinogens in experimental animals. [Hawley] Sources of exposure include cigarette smoking, cured or smoked meat and fish, metalworking fluids, rubber vulcanization, leather tanning, and endogenous nitrosation of drugs in the stomach. [Rom, p. 1229-31]
Hawley - Lewis RJ. _Hawley's Condensed Chemical Dictionary, _15th Ed. New York: John Wiley & Sons, 2007.
Rom - Rom WN (ed). _Environmental and Occupational Medicine, _4th Ed. Philadelphia: Lippincott Williams & Wilkins, 2007., p. 1229-31
Industrial Processes with risk of exposure

Metal Preparation and Pouring [Category: Foundry]

Metal Machining [Category: Heat or Machine]

Leather Tanning and Processing [Category: Industry]

Activities with risk of exposure
Smoking cigarettes [Category: Food & Drugs]

7 Safety and Hazards

7.1 Hazards Identification

7.1.1 Hazards Summary

The acute toxicity of the dialkylnitrosamines decreases with increasing chain length. [ACGIH] Appreciation of the carcinogenicity of the nitrosamines has led to their characterization in many occupational and environmental circumstances. N-nitrosodimethylamine (NDMA) has caused fatal hepatic necrosis after acute exposure and liver cirrhosis after chronic exposure. [LaDou, p. 507-8]
ACGIH - Documentation of the TLVs and BEIs, 7th Ed. Cincinnati: ACGIH Worldwide, 2020.
LaDou - LaDou J, Harrison R (eds). Current Occupational & Environmental Medicine, 5th Ed. New York: McGraw-Hill, 2014., p. 507-8

7.2 Stability and Reactivity

7.2.1 Air and Water Reactions

No rapid reaction with air. No rapid reaction with water.

7.2.2 Reactive Group

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

7.2.3 Reactivity Alerts

Strong Oxidizing Agent

7.2.4 Reactivity Profile

Nitrated organics, such as NITROSAMINES, range from slight to strong oxidizing agents. If mixed with reducing agents, including hydrides, sulfides and nitrides, they may begin a vigorous reaction.

8 Toxicity

8.1 Toxicological Information

8.1.1 Adverse Effects

Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.

9 Associated Disorders and Diseases

10 Literature

10.1 Consolidated References

10.2 NLM Curated PubMed Citations

10.3 Springer Nature References

10.4 Thieme References

10.5 Chemical Co-Occurrences in Literature

10.6 Chemical-Gene Co-Occurrences in Literature

10.7 Chemical-Disease Co-Occurrences in Literature

11 Patents

11.1 Depositor-Supplied Patent Identifiers

11.2 WIPO PATENTSCOPE

11.3 Chemical Co-Occurrences in Patents

11.4 Chemical-Disease Co-Occurrences in Patents

11.5 Chemical-Gene Co-Occurrences in Patents

12 Interactions and Pathways

12.1 Chemical-Target Interactions

13 Biological Test Results

13.1 BioAssay Results

14 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

15 Classification

15.1 MeSH Tree

15.2 NCI Thesaurus Tree

15.3 ChemIDplus

15.4 EPA DSSTox Classification

15.5 LOTUS Tree

15.6 EPA Substance Registry Services Tree

15.7 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. CAMEO Chemicals
    LICENSE
    CAMEO Chemicals and all other CAMEO products are available at no charge to those organizations and individuals (recipients) responsible for the safe handling of chemicals. However, some of the chemical data itself is subject to the copyright restrictions of the companies or organizations that provided the data.
    https://cameochemicals.noaa.gov/help/reference/terms_and_conditions.htm?d_f=false
  2. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  5. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  6. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  8. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  9. Japan Chemical Substance Dictionary (Nikkaji)
  10. KNApSAcK Species-Metabolite Database
  11. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  12. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  13. Springer Nature
  14. SpringerMaterials
  15. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  16. Wikidata
  17. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  18. PubChem
  19. EPA Substance Registry Services
  20. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  21. PATENTSCOPE (WIPO)
CONTENTS