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Nile Blue chloride

PubChem CID
16938
Structure
Nile Blue chloride_small.png
Nile Blue chloride_3D_Structure.png
Molecular Formula
Synonyms
  • Nile Blue chloride
  • 2381-85-3
  • Basic Blue 12
  • Nile blue
  • Nile Blue A
Molecular Weight
353.8 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-08-08
  • Modify:
    2025-01-04
Description
Nile blue A is an organic chloride salt having 5-amino-9-(diethylamino)benzo[a]phenoxazin-7-ium as the couterion. fluorescent dye which is also a potent photosensitiser for photodynamic therapy. It has a role as a fluorochrome and a histological dye. It contains a nile blue(1+).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Nile Blue chloride.png

1.2 3D Conformer

3D Conformer of Parent

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(5-aminobenzo[a]phenoxazin-9-ylidene)-diethylazanium;chloride
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C20H19N3O.ClH/c1-3-23(4-2)13-9-10-17-18(11-13)24-19-12-16(21)14-7-5-6-8-15(14)20(19)22-17;/h5-12,21H,3-4H2,1-2H3;1H
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

SHXOKQKTZJXHHR-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC[N+](=C1C=CC2=NC3=C(C=C(C4=CC=CC=C43)N)OC2=C1)CC.[Cl-]
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C20H20N3O.Cl
C20H20ClN3O
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2381-85-3

2.3.3 Deprecated CAS

1026018-39-2, 1026232-05-2, 105480-57-7, 1063750-19-5, 114567-73-6, 20517-93-5, 298209-62-8, 299426-03-2, 348637-62-7, 415902-65-7, 832733-89-8, 874358-59-5, 89168-53-6, 898282-92-3, 927191-06-8

2.3.4 European Community (EC) Number

2.3.5 UNII

2.3.6 ChEBI ID

2.3.7 ChEMBL ID

2.3.8 DSSTox Substance ID

2.3.9 NSC Number

2.3.10 Wikidata

2.3.11 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Cresyl Fast Violet
  • Nile Blue
  • nile blue A perchlorate
  • Nile Blue perchlorate
  • nile blue sulfate
  • Nile Blue tetrafluoroborate

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
353.8 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
353.1294900 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
353.1294900 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
50.6 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
25
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
625
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
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
2
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

Green, blue, steel gray, or black powder; [Acros Organics MSDS]

3.2.2 Dissociation Constants

3.3 Chemical Classes

Dyes -> Azine Dyes

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

Copyright
Copyright © 2016-2024 Chemical Block, Russia, Leninsky Prospect 47 - Database Compilation Copyright © 2016-2021 John Wiley & Sons, Inc. All Rights Reserved.
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4.2 IR Spectra

4.2.1 FTIR Spectra

Technique
Mull
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich
Catalog Number
222550
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.2.2 ATR-IR Spectra

Source of Sample
Sigma-Aldrich
Catalog Number
222550
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

6 Chemical Vendors

7 Pharmacology and Biochemistry

7.1 MeSH Pharmacological Classification

Fluorescent Dyes
Chemicals that emit light after excitation by light. The wave length of the emitted light is usually longer than that of the incident light. Fluorochromes are substances that cause fluorescence in other substances, i.e., dyes used to mark or label other compounds with fluorescent tags. (See all compounds classified as Fluorescent Dyes.)

8 Use and Manufacturing

8.1 General Manufacturing Information

EPA TSCA Commercial Activity Status
Benzo[a]phenoxazin-7-ium, 5-amino-9-(diethylamino)-, chloride (1:1): ACTIVE

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 Hazards Summary

Causes lung changes in intravenous lethal-dose studies of mice (LDLo = 33 mg/kg); [RTECS] May cause irritation; [Acros Organics MSDS] See Cresyl violet acetate.

9.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: Benzo[a]phenoxazin-7-ium, 5-amino-9-(diethylamino)-, chloride

10 Toxicity

10.1 Toxicological Information

10.1.1 Acute Effects

11 Literature

11.1 Consolidated References

11.2 NLM Curated PubMed Citations

11.3 Springer Nature References

11.4 Thieme References

11.5 Chemical Co-Occurrences in Literature

11.6 Chemical-Gene Co-Occurrences in Literature

11.7 Chemical-Disease Co-Occurrences in Literature

12 Patents

12.1 Depositor-Supplied Patent Identifiers

12.2 WIPO PATENTSCOPE

12.3 Chemical Co-Occurrences in Patents

12.4 Chemical-Disease Co-Occurrences in Patents

12.5 Chemical-Gene Co-Occurrences in Patents

13 Biological Test Results

13.1 BioAssay Results

14 Classification

14.1 MeSH Tree

14.2 ChEBI Ontology

14.3 ChemIDplus

14.4 NORMAN Suspect List Exchange Classification

14.5 EPA DSSTox Classification

14.6 EPA TSCA and CDR Classification

14.7 EPA Substance Registry Services Tree

14.8 MolGenie Organic Chemistry Ontology

15 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    Benzo[a]phenoxazin-7-ium, 5-amino-9-(diethylamino)-, chloride
    https://services.industrialchemicals.gov.au/search-inventory/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. 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
  4. EPA Chemicals under the TSCA
    Benzo[a]phenoxazin-7-ium, 5-amino-9-(diethylamino)-, chloride (1:1)
    https://www.epa.gov/chemicals-under-tsca
    EPA TSCA Classification
    https://www.epa.gov/tsca-inventory
  5. EPA DSSTox
    5-Amino-9-(diethylamino)benzo(a)phenoxazin-7-ium chloride
    https://comptox.epa.gov/dashboard/DTXSID40883834
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  6. 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
    5-amino-9-(diethylamino)benzo[a]phenoxazin-7-ium chloride
    https://echa.europa.eu/substance-information/-/substanceinfo/100.017.439
  7. 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
  8. ChEBI
  9. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  10. 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
  11. IUPAC Digitized pKa Dataset
  12. SpectraBase
    9-(diethylamino)-5H-benzo[a]phenoxazin-5-iminium chloride
    https://spectrabase.com/spectrum/I6vM95AjhLq
  13. Springer Nature
  14. 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/
  15. Wikidata
    N,N-Diethyl-5-imino-5H-benzo[a]phenoxazin-9-amine--hydrogen chloride (1/1)
    https://www.wikidata.org/wiki/Q82879185
  16. Wikipedia
  17. PubChem
  18. 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
  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/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  20. EPA Substance Registry Services
  21. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  22. PATENTSCOPE (WIPO)
CONTENTS