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9H-Pyrido[3,4-B]indole

PubChem CID
64961
Structure
9H-Pyrido[3,4-B]indole_small.png
9H-Pyrido[3,4-B]indole_3D_Structure.png
9H-Pyrido[3,4-B]indole__Crystal_Structure.png
Molecular Formula
Synonyms
  • 9H-Pyrido[3,4-B]indole
  • Norharman
  • 244-63-3
  • Norharmane
  • beta-Carboline
Molecular Weight
168.19 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-26
  • Modify:
    2025-01-11
Description
Beta-carboline is the parent compound of the beta-carbolines, a tricyclic structure comprising an indole ring system ortho- fused to C-3 and C-4 of a pyridine ring. It has a role as a marine metabolite and a fungal metabolite. It is a member of beta-carbolines and a mancude organic heterotricyclic parent.
9H-Pyrido[3,4-B]indole has been reported in Polygala tenuifolia, Streptomyces nigra, and other organisms with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
9H-Pyrido[3,4-B]indole.png

1.2 3D Conformer

1.3 Crystal Structures

1 of 4
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CCDC Number
Crystal Structure Data
Crystal Structure Depiction
Crystal Structure Depiction

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

9H-pyrido[3,4-b]indole
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

C1=CC=C2C(=C1)C3=C(N2)C=NC=C3
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C11H8N2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DSSTox Substance ID

2.3.8 HMDB ID

2.3.9 KEGG ID

2.3.10 Metabolomics Workbench ID

2.3.11 Nikkaji Number

2.3.12 NSC Number

2.3.13 Pharos Ligand ID

2.3.14 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • beta-carboline
  • norharman
  • norharman hydrochloride
  • norharmane
  • norhormane

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
168.19 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
3.2
Reference
Computed by XLogP3 3.0 (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
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
168.068748264 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
168.068748264 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
28.7 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
13
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
193
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
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

Solid

3.2.2 Melting Point

199 °C

3.2.3 Solubility

>25.2 [ug/mL] (The mean of the results at pH 7.4)

3.2.4 LogP

3.17
BIAGI,GL ET AL. (1989)

3.2.5 Collision Cross Section

132.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

139.48 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

130.92 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Ross et al. JASMS 2022; 33; 1061-1072. DOI:10.1021/jasms.2c00111

3.2.6 Kovats Retention Index

Standard non-polar
2005
Semi-standard non-polar
2009

3.3 SpringerMaterials Properties

3.4 Chemical Classes

other cyclic peptide (other cyclic peptide)
S75 | CyanoMetDB | Comprehensive database of secondary metabolites from cyanobacteria | DOI:10.5281/zenodo.4551528 | DOI:10.1007/s10811-005-7292-7

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.1.1 1H NMR Spectra

1 of 2
Instrument Name
Varian CFT-20
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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2 of 2
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Sigma-Aldrich Co. LLC.
Catalog Number
N33101
Copyright
Copyright © 2021-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2021 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 2
Instrument Name
Jeol FX-90
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. 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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4.1.3 15N NMR Spectra

Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 9
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Spectra ID
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

168.0 99.99

140.0 32.11

114.0 23.06

84.0 19.52

113.0 15.84

Thumbnail
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Notes
instrument=VARIAN MAT-44S
2 of 9
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MoNA ID
MS Category
Experimental
MS Type
GC-MS
MS Level
MS1
Instrument
VARIAN MAT-44S
Instrument Type
EI-B
Ionization Mode
positive
Top 5 Peaks

168 99.99

140 32.11

114 23.06

84 19.52

113 15.84

Thumbnail
Thumbnail
License
CC BY-NC-SA

4.2.2 MS-MS

1 of 8
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Spectra ID
Instrument Type
ESI-QFT
Ionization Mode
negative
Top 5 Peaks

167.0605 88.92

168.0639 10.12

149.0086 0.96

Thumbnail
Thumbnail
Notes
adduct_type [M-H]- original_collision_energy 35HCD CannabisDB spectra from MoNa 2020 June Thermo Q Exactive HF Vaniya/Fiehn Natural Products Library
2 of 8
View All
Spectra ID
Instrument Type
ESI-QFT
Ionization Mode
negative
Top 5 Peaks

167.0605 89.01

168.0639 9.92

149.0084 1.08

Thumbnail
Thumbnail
Notes
adduct_type [M-H]- original_collision_energy 45HCD CannabisDB spectra from MoNa 2020 June Thermo Q Exactive HF Vaniya/Fiehn Natural Products Library

4.2.3 LC-MS

1 of 36
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Authors
ACESx, Jonathan W. Martin Group
Instrument
QExactive Orbitrap HF-X (Thermo Scientific)
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
Ramp 20%-70% (nominal)
Fragmentation Mode
HCD
Column Name
Waters; Acquity UPLC BEH C18, 2.1 x 100 mm, 1.7 um, Waters
Retention Time
13.2891
Top 5 Peaks

169.07527 999

169.07704 996

115.05421 28

168.0681 18

142.06561 15

Thumbnail
Thumbnail
License
CC BY
2 of 36
View All
Authors
ACESx, Jonathan W. Martin Group
Instrument
QExactive Orbitrap HF-X (Thermo Scientific)
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
NEGATIVE
Ionization
ESI
Collision Energy
Ramp 20%-70% (nominal)
Fragmentation Mode
HCD
Column Name
Waters; Acquity UPLC BEH C18, 2.1 x 100 mm, 1.7 um, Waters
Retention Time
13.1169
Precursor m/z
167.0618
Top 5 Peaks

167.06178 999

140.05107 14

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License
CC BY

4.2.4 Other MS

1 of 5
View All
Authors
ACESx, Jonathan W. Martin Group
Instrument
QExactive Orbitrap HF-X (Thermo Scientific)
Instrument Type
LC-APCI-QFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
APCI
Collision Energy
Ramp 20%-70% (nominal)
Fragmentation Mode
HCD
Column Name
Waters; Acquity UPLC BEH C18, 2.1 x 100 mm, 1.7 um, Waters
Retention Time
13.1507
Precursor m/z
169.076
Top 5 Peaks

169.07631 999

115.05412 18

168.06824 13

142.06549 10

Thumbnail
Thumbnail
License
CC BY
2 of 5
View All
Authors
MASS SPECTROSCOPY SOC. OF JAPAN (MSSJ)
Instrument
VARIAN MAT-44S
Instrument Type
EI-B
MS Level
MS
Ionization Mode
POSITIVE
Ionization
ENERGY 75 eV
Top 5 Peaks

168 999

140 321

114 231

84 195

113 158

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License
CC BY-NC-SA

4.3 IR Spectra

4.3.1 FTIR Spectra

1 of 2
Technique
KBr WAFER
Source of Sample
Aldrich Chemical Company, Inc., Milwaukee, Wisconsin
Catalog Number
N3310
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail
2 of 2
Technique
Mull
Source of Spectrum
Sigma-Aldrich Co. LLC.
Source of Sample
Aldrich
Catalog Number
N33101
Copyright
Copyright © 2018-2024 Sigma-Aldrich Co. LLC. - Database Compilation Copyright © 2018-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.3.2 ATR-IR Spectra

Instrument Name
Bio-Rad FTS
Technique
ATR-Neat
Source of Spectrum
Forensic Spectral Research
Source of Sample
Cayman Chemical Company
Catalog Number
<a href=https://www.caymanchem.com/product/33845>33845</a>
Lot Number
0625228-6
Copyright
Copyright © 2019-2024 John Wiley & Sons, Inc. All Rights Reserved.
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Thumbnail

4.4 Raman Spectra

Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Cayman Chemical Company
Catalog Number
<a href=https://www.caymanchem.com/product/33845>33845</a>
Lot Number
0625228-6
Copyright
Copyright © 2015-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Food Additives and Ingredients

7.1 Associated Foods

8 Pharmacology and Biochemistry

8.1 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.)
Mutagens
Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes. (See all compounds classified as Mutagens.)

9 Use and Manufacturing

9.1 Uses

Synthetic Polymer MALDI Matrix Compounds

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (50%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (50%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, 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 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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.

10.1.2 Hazard Classes and Categories

Acute Tox. 4 (100%)

Skin Irrit. 2 (50%)

Eye Irrit. 2A (50%)

STOT SE 3 (50%)

11 Toxicity

11.1 Toxicological Information

11.1.1 Acute Effects

12 Associated Disorders and Diseases

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Thieme References

13.5 Wiley References

13.6 Chemical Co-Occurrences in Literature

13.7 Chemical-Gene Co-Occurrences in Literature

13.8 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 Chemical Co-Occurrences in Patents

14.4 Chemical-Disease Co-Occurrences in Patents

14.5 Chemical-Gene Co-Occurrences in Patents

15 Interactions and Pathways

15.1 Protein Bound 3D Structures

15.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

15.2 Chemical-Target Interactions

16 Biological Test Results

16.1 BioAssay Results

17 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106
S75 | CyanoMetDB | Comprehensive database of secondary metabolites from cyanobacteria | DOI:10.5281/zenodo.4551528

18 Classification

18.1 MeSH Tree

18.2 ChEBI Ontology

18.3 ChemIDplus

18.4 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

18.5 ChEMBL Target Tree

18.6 UN GHS Classification

18.7 NORMAN Suspect List Exchange Classification

18.8 CCSBase Classification

18.9 EPA DSSTox Classification

18.10 The Natural Products Atlas Classification

18.11 NIST Synthetic Polymer MALDI Recipes Database Classification

18.12 LOTUS Tree

18.13 MolGenie Organic Chemistry Ontology

19 Information Sources

  1. Burnham Center for Chemical Genomics
  2. CAS Common Chemistry
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    https://creativecommons.org/licenses/by-nc/4.0/
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    https://www.cancer.gov/policies/copyright-reuse
  5. EPA DSSTox
    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
  7. FDA Global Substance Registration System (GSRS)
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  8. Human Metabolome Database (HMDB)
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    http://www.hmdb.ca/citing
  9. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  10. ChEBI
  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. 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
  13. 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
  14. IUPHAR/BPS Guide to PHARMACOLOGY
    LICENSE
    The Guide to PHARMACOLOGY database is licensed under the Open Data Commons Open Database License (ODbL) https://opendatacommons.org/licenses/odbl/. Its contents are licensed under a Creative Commons Attribution-ShareAlike 4.0 International License (http://creativecommons.org/licenses/by-sa/4.0/)
    https://www.guidetopharmacology.org/about.jsp#license
    Guide to Pharmacology Target Classification
    https://www.guidetopharmacology.org/targets.jsp
  15. Therapeutic Target Database (TTD)
  16. Crystallography Open Database (COD)
    LICENSE
    All data in the COD and the database itself are dedicated to the public domain and licensed under the CC0 License. Users of the data should acknowledge the original authors of the structural data.
    https://creativecommons.org/publicdomain/zero/1.0/
  17. The Cambridge Structural Database
  18. FooDB
    LICENSE
    FooDB 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 (FooDB) and the original publication.
    https://foodb.ca/about
  19. 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
  20. 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
  21. SpectraBase
  22. Japan Chemical Substance Dictionary (Nikkaji)
  23. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  24. KNApSAcK Species-Metabolite Database
  25. Natural Product Activity and Species Source (NPASS)
  26. 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/
    Norharmane (9H-pyrido(3,4-b)indole
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  27. MassBank Europe
  28. Metabolomics Workbench
  29. NIST Synthetic Polymer MALDI Recipes Database
    LICENSE
    Formerly known as NIST Standard Reference Database 172
    https://www.nist.gov/disclaimer
    9H-pyrido [3,4-b]indol (norharmane, β-carboline)
    https://maldi.nist.gov/
  30. NMRShiftDB
  31. Pharos
    LICENSE
    Data accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.
    https://pharos.nih.gov/about
  32. Protein Data Bank in Europe (PDBe)
  33. 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
  34. Springer Nature
  35. SpringerMaterials
  36. 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/
  37. Wikidata
  38. Wiley
  39. PubChem
  40. Medical Subject Headings (MeSH)
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    https://www.nlm.nih.gov/copyright.html
  41. GHS Classification (UNECE)
  42. 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/
  43. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  44. PATENTSCOPE (WIPO)
  45. NCBI
CONTENTS