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N-Butylbenzenesulfonamide

PubChem CID
19241
Structure
N-Butylbenzenesulfonamide_small.png
N-Butylbenzenesulfonamide_3D_Structure.png
Molecular Formula
Synonyms
  • N-BUTYLBENZENESULFONAMIDE
  • 3622-84-2
  • Benzenesulfonamide, N-butyl-
  • N-n-Butylbenzenesulfonamide
  • Plastomoll BMB
Molecular Weight
213.30 g/mol
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-04
Description
N-butylbenzenesulfonamide is a sulfonamide that is benzenesulfonamide substituted by a butyl group at the nitrogen atom. It has been isolated from the plant Prunus africana and has been shown to exhibit antiandrogenic activity. It has a role as a neurotoxin and a plant metabolite.
N-Butylbenzenesulfonamide has been reported in Streptomyces, Pseudomonas, and other organisms with data available.
N-Butyl benzenesulfonamide (NBBS), a plasticizer used commercially in the polymerization of polyamide compounds. It is neurotoxic and has been found to induce spastic myelopathy in rabbits.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
N-Butylbenzenesulfonamide.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-butylbenzenesulfonamide
Computed by Lexichem TK 2.7.0 (PubChem release 2024.11.20)

2.1.2 InChI

InChI=1S/C10H15NO2S/c1-2-3-9-11-14(12,13)10-7-5-4-6-8-10/h4-8,11H,2-3,9H2,1H3
Computed by InChI 1.07.0 (PubChem release 2024.11.20)

2.1.3 InChIKey

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

2.1.4 SMILES

CCCCNS(=O)(=O)C1=CC=CC=C1
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C10H15NO2S
Computed by PubChem 2.2 (PubChem release 2024.11.20)

2.3 Other Identifiers

2.3.1 CAS

3622-84-2

2.3.2 Deprecated CAS

1028684-14-1, 2102595-95-7

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DrugBank ID

2.3.8 DSSTox Substance ID

2.3.9 Metabolomics Workbench ID

2.3.10 Nikkaji Number

2.3.11 NSC Number

2.3.12 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • N-butylbenzenesulfonamide
  • N-butylbenzenesulphonamide
  • NBBS

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
213.30 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
XLogP3-AA
Property Value
2.1
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
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Exact Mass
Property Value
213.08234989 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Monoisotopic Mass
Property Value
213.08234989 Da
Reference
Computed by PubChem 2.2 (PubChem release 2024.11.20)
Property Name
Topological Polar Surface Area
Property Value
54.6 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2024.11.20)
Property Name
Heavy Atom Count
Property Value
14
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
237
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 Experimental Properties

3.2.1 Physical Description

Liquid; Pellets or Large Crystals
Colorless oily liquid with nearly no odor; [EPA ChAMP: Submission]

3.2.2 Boiling Point

314 °C

3.2.3 Kovats Retention Index

Semi-standard non-polar
1794 , 1797
Standard polar
2956

3.3 Chemical Classes

Nitrogen Compounds -> Sulfonamides

3.3.1 Drugs

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749

3.3.2 Plasticizers

Plasticizer
S47 | ECHAPLASTICS | A list from the Plastic Additives Initiative Mapping Exercise by ECHA | DOI:10.5281/zenodo.2658139

3.3.3 Polymers

Plastics -> Plasticisers
S47 | ECHAPLASTICS | A list from the Plastic Additives Initiative Mapping Exercise by ECHA | DOI:10.5281/zenodo.2658139
Plastics -> PUR; PA
S47 | ECHAPLASTICS | A list from the Plastic Additives Initiative Mapping Exercise by ECHA | DOI:10.5281/zenodo.2658139

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
BRUKER AC-300
Source of Sample
Tokyo Kasei Kogyo Company, Ltd., Tokyo, Japan
Copyright
Copyright © 1991-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Varian A-60
Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.1.2 13C NMR Spectra

1 of 2
Source of Sample
Tokyo Kasei Kogyo Company, Ltd., Tokyo, Japan
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Instrument Name
Varian XL-100
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 4
View All
NIST Number
125067
Library
Main library
Total Peaks
92
m/z Top Peak
77
m/z 2nd Highest
141
m/z 3rd Highest
170
Thumbnail
Thumbnail
2 of 4
View All
NIST Number
232333
Library
Replicate library
Total Peaks
93
m/z Top Peak
77
m/z 2nd Highest
141
m/z 3rd Highest
170
Thumbnail
Thumbnail

4.2.2 LC-MS

1 of 17
View All
Authors
Nikiforos Alygizakis, Katerina Galani, Nikolaos Thomaidis, University of Athens
Instrument
Bruker maXis Impact
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
10 eV
Fragmentation Mode
CID
Column Name
Acclaim RSLC C18 2.2um, 2.1x100mm, Thermo
Retention Time
7.724 min
Precursor m/z
214.0896
Precursor Adduct
[M+H]+
Top 5 Peaks

158.0262 999

214.0895 571

140.9996 465

215.0921 72

159.0297 70

Thumbnail
Thumbnail
License
CC BY
2 of 17
View All
Authors
Nikiforos Alygizakis, Katerina Galani, Nikolaos Thomaidis, University of Athens
Instrument
Bruker maXis Impact
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
20 eV
Fragmentation Mode
CID
Column Name
Acclaim RSLC C18 2.2um, 2.1x100mm, Thermo
Retention Time
7.742 min
Precursor m/z
214.0896
Precursor Adduct
[M+H]+
Top 5 Peaks

140.9994 999

158.0265 327

142.0033 98

142.9946 42

159.0287 26

Thumbnail
Thumbnail
License
CC BY

4.3 IR Spectra

4.3.1 FTIR Spectra

1 of 2
Technique
BETWEEN SALTS
Source of Sample
BASF AG / BASF Corporation
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
NEAT
Source of Sample
The C.P. Hall Company
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.3.2 ATR-IR Spectra

Source of Sample
Aldrich
Catalog Number
B90653
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.3.3 Vapor Phase IR Spectra

Instrument Name
DIGILAB FTS-14
Technique
Vapor Phase
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 MeSH Pharmacological Classification

Neurotoxins
Toxic substances from microorganisms, plants or animals that interfere with the functions of the nervous system. Most venoms contain neurotoxic substances. Myotoxins are included in this concept. (See all compounds classified as Neurotoxins.)
Plasticizers
Materials incorporated mechanically in plastics (usually PVC) to increase flexibility, workability or distensibility; due to the non-chemical inclusion, plasticizers leach out from the plastic and are found in body fluids and the general environment. (See all compounds classified as Plasticizers.)

8 Use and Manufacturing

8.1 Uses

EPA CPDat Chemical and Product Categories
The Chemical and Products Database, a resource for exposure-relevant data on chemicals in consumer products, Scientific Data, volume 5, Article number: 180125 (2018), DOI:10.1038/sdata.2018.125
Sources/Uses
Used in the polymers and textile processing industries; Used as a plasticizer, smelting agent for moulding, and softener; [IUCLID] Used mainly as a plasticizer; [EPA ChAMP: Submission]
Industrial Processes with risk of exposure
Plastics -> Typical concentration range in plastic materials -> 10.0 - 15.0%
S47 | ECHAPLASTICS | A list from the Plastic Additives Initiative Mapping Exercise by ECHA | DOI:10.5281/zenodo.2658139
N-Butyl benzenesulfonamide (NBBS), a plasticizer used commercially in the polymerization of polyamide compounds. It is neurotoxic and has been found to induce spastic myelopathy in rabbits.

8.1.1 Use Classification

Plastics -> Polymer Type -> PUR; PA
S47 | ECHAPLASTICS | A list from the Plastic Additives Initiative Mapping Exercise by ECHA | DOI:10.5281/zenodo.2658139
Plastics -> Plasticisers
S47 | ECHAPLASTICS | A list from the Plastic Additives Initiative Mapping Exercise by ECHA | DOI:10.5281/zenodo.2658139

8.1.2 Industry Uses

  • Plasticizer
  • Intermediate
  • Other (specify)
  • Plasticizers

8.1.3 Consumer Uses

Plasticizers

8.2 U.S. Production

Aggregated Product Volume

2019: 1,000,000 - <10,000,000 lb

2018: 1,000,000 - <10,000,000 lb

2017: 1,000,000 - <10,000,000 lb

2016: 1,000,000 - <10,000,000 lb

8.3 General Manufacturing Information

Industry Processing Sectors
  • Plastics Material and Resin Manufacturing
  • Plastics Product Manufacturing
  • Transportation Equipment Manufacturing
  • Miscellaneous Manufacturing
EPA TSCA Commercial Activity Status
Benzenesulfonamide, N-butyl-: ACTIVE

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Note
Pictograms displayed are for 83.6% (494 of 591) of reports that indicate hazard statements. This chemical does not meet GHS hazard criteria for 16.4% (97 of 591) of reports.
Pictogram(s)
Health Hazard
Signal
Warning
GHS Hazard Statements

H373 (79%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]

H412 (81%): Harmful to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P260, P273, P319, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 591 reports by companies from 18 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria per 97 of 591 reports by companies. For more detailed information, please visit ECHA C&L website.

There are 17 notifications provided by 494 of 591 reports by companies with hazard statement code(s).

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

9.1.2 Hazard Classes and Categories

STOT RE 2 (79%)

Aquatic Chronic 3 (81%)

9.1.3 Hazards Summary

Not an eye irritant in guinea pigs; Causes mild eye irritation in rabbits (classified by the EC as irritating); [IUCLID] A 28-day oral study of rats produced 100% mortality at the highest tested dose (1,000 mg/kg/day); Low frequency and severity of nerve fiber degeneration in the spinal cord and sciatic nerves, liver enlargement, hepatocyte hypertrophy, thymic atrophy at 150 mg/kg/day; No changes in functional performance observations, body weight/food consumption, or altered clinical biochemistry at 50 and 150 mg/kg/day (NOAEL of 50 mg/kg/day); [EPA ChAMP: Submission] Human inhalation of 3.7 mg/m3 causes conjunctive irritation and structural or functional changes in trachea or bronchi; [RTECS] A skin and strong eye irritant; [Sigma-Aldrich MSDS]

9.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Benzenesulfonamide, N-butyl-
REACH Registered Substance
New Zealand EPA Inventory of Chemical Status
Benzenesulfonamide, N-butyl-: Does not have an individual approval but may be used under an appropriate group standard

10 Toxicity

10.1 Toxicological Information

10.1.1 Carcinogen Classification

Carcinogen Classification
No indication of carcinogenicity to humans (not listed by IARC).

10.1.2 Adverse Effects

Neurotoxin - Other CNS neurotoxin

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.

10.1.3 Acute Effects

10.1.4 Toxicity Data

LCLo (rat) = 385 mg/m3/4hr

11 Associated Disorders and Diseases

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Thieme References

12.5 Chemical Co-Occurrences in Literature

12.6 Chemical-Gene Co-Occurrences in Literature

12.7 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Protein Bound 3D Structures

14.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Conformer

14.2 Chemical-Target Interactions

15 Biological Test Results

15.1 BioAssay Results

16 Taxonomy

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

17 Classification

17.1 MeSH Tree

17.2 ChEBI Ontology

17.3 ChemIDplus

17.4 ChEMBL Target Tree

17.5 UN GHS Classification

17.6 EPA CPDat Classification

17.7 NORMAN Suspect List Exchange Classification

17.8 EPA DSSTox Classification

17.9 The Natural Products Atlas Classification

17.10 EPA TSCA and CDR Classification

17.11 LOTUS Tree

17.12 EPA Substance Registry Services Tree

17.13 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
  2. CAS Common Chemistry
    LICENSE
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    https://creativecommons.org/licenses/by-nc/4.0/
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  4. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
    N-Butyl-Benzenesulfonamide
    https://www.drugbank.ca/drugs/DB02055
  5. DTP/NCI
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    https://www.cancer.gov/policies/copyright-reuse
  6. EPA Chemical Data Reporting (CDR)
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    https://www.epa.gov/web-policies-and-procedures/epa-disclaimers#copyright
  7. EPA Chemicals under the TSCA
    Benzenesulfonamide, N-butyl-
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  8. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  9. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    N-butylbenzenesulphonamide
    https://chem.echa.europa.eu/100.020.749
  10. FDA Global Substance Registration System (GSRS)
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  11. New Zealand Environmental Protection Authority (EPA)
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    This work is licensed under the Creative Commons Attribution-ShareAlike 4.0 International licence.
    https://www.epa.govt.nz/about-this-site/general-copyright-statement/
  12. ChEBI
  13. 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/
  14. Toxin and Toxin Target Database (T3DB)
    LICENSE
    T3DB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (T3DB) and the original publication.
    http://www.t3db.ca/downloads
    N-Butyl-Benzenesulfonamide
    http://www.t3db.ca/toxins/T3D4810
  15. ChEMBL
    LICENSE
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    http://www.ebi.ac.uk/Information/termsofuse.html
  16. 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
  17. EPA Chemical and Products Database (CPDat)
  18. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
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    https://haz-map.com/About
    N-Butylbenzenesulfonamide
    https://haz-map.com/Agents/15834
  19. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    N-Butylbenzenesulfonamide
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  20. Japan Chemical Substance Dictionary (Nikkaji)
  21. KNApSAcK Species-Metabolite Database
  22. Natural Product Activity and Species Source (NPASS)
  23. MassBank Europe
  24. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  25. Metabolomics Workbench
  26. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
    Benzenesulfonamide, N-butyl-
    http://www.nist.gov/srd/nist1a.cfm
  27. SpectraBase
  28. NMRShiftDB
  29. Protein Data Bank in Europe (PDBe)
  30. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  31. Springer Nature
  32. Thieme Chemistry
    LICENSE
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    https://creativecommons.org/licenses/by-nc-nd/4.0/
  33. Wikidata
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  35. Medical Subject Headings (MeSH)
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    https://www.nlm.nih.gov/copyright.html
  36. GHS Classification (UNECE)
  37. The Natural Products Atlas
    LICENSE
    The Natural Products Atlas is licensed under a Creative Commons Attribution 4.0 International License.
    https://www.npatlas.org/terms
    The Natural Products Atlas Classification
    https://www.npatlas.org/
  38. EPA Substance Registry Services
  39. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  40. PATENTSCOPE (WIPO)
CONTENTS