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Noscapine Hydrochloride

PubChem CID
9933439
Structure
Noscapine Hydrochloride_small.png
Noscapine Hydrochloride_3D_Structure.png
Molecular Formula
Synonyms
  • Noscapine hydrochloride
  • Noscapine HCl
  • 912-60-7
  • Noscapine hydrchloride
  • Narcotine hydrochloride
Molecular Weight
449.9 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Parent Compound
Dates
  • Create:
    2006-10-25
  • Modify:
    2025-01-04
Description
Noscapine Hydrochloride is the orally available hydrochloride salt of the opioid agonist noscapine, a phthalideisoquinoline alkaloid derived from the opium poppy Papaver somniferum, with mild analgesic, antitussive, and potential antineoplastic activities. Noscapine binds to tubulin and alters its conformation, resulting in a disruption of the dynamics of microtubule assembly (by increasing the time that microtubules spend idle in a paused state) and subsequently, the inhibition of mitosis and tumor cell death. Unlike other tubulin inhibitors such as the taxanes and vinca alkaloids, noscapine does not affect microtubule polymerization.
A naturally occurring opium alkaloid that is a centrally acting antitussive agent.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Noscapine Hydrochloride.png

1.2 3D Conformer

3D Conformer of Parent

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3S)-6,7-dimethoxy-3-[(5R)-4-methoxy-6-methyl-7,8-dihydro-5H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl]-3H-2-benzofuran-1-one;hydrochloride
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C22H23NO7.ClH/c1-23-8-7-11-9-14-20(29-10-28-14)21(27-4)15(11)17(23)18-12-5-6-13(25-2)19(26-3)16(12)22(24)30-18;/h5-6,9,17-18H,7-8,10H2,1-4H3;1H/t17-,18+;/m1./s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

MFLVZFXCSKVCSH-URBRKQAFSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CN1CCC2=CC3=C(C(=C2[C@@H]1[C@@H]4C5=C(C(=C(C=C5)OC)OC)C(=O)O4)OC)OCO3.Cl
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C22H23NO7.ClH
C22H24ClNO7
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

912-60-7
219533-73-0

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEMBL ID

2.3.5 DSSTox Substance ID

2.3.6 KEGG ID

2.3.7 NCI Thesaurus Code

2.3.8 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Capval
  • Capval Tropfen
  • Embonate, Noscapine Hydrogen
  • Hydrochloride, Noscapine
  • Hydrogen Embonate, Noscapine
  • Librochin prikkelhoest
  • Narcotine
  • Noscapect
  • Noscapine
  • Noscapine Hydrochloride
  • Noscapine Hydrogen Embonate
  • prikkelhoest, Librochin
  • Tropfen, Capval
  • Tuscalman

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
449.9 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
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
449.1241298 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
449.1241298 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
75.7Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
31
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
647
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
2
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 Collision Cross Section

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

5 Chemical Vendors

6 Drug and Medication Information

6.1 Clinical Trials

6.1.1 ClinicalTrials.gov

7 Pharmacology and Biochemistry

7.1 MeSH Pharmacological Classification

Antitussive Agents
Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally. (See all compounds classified as Antitussive Agents.)

8 Safety and Hazards

8.1 Hazards Identification

8.1.1 GHS Classification

1 of 2
View All
Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements
H302 (97.9%): Harmful if swallowed [Warning Acute toxicity, oral]
Precautionary Statement Codes

P264, P270, P301+P317, P330, 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 48 reports by companies from 4 notifications to the ECHA C&L Inventory.

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.

8.1.2 Hazard Classes and Categories

Acute Tox. 4 (97.9%)
Acute Tox. 4 (100%)

8.2 Regulatory Information

The Australian Inventory of Industrial Chemicals
Chemical: 1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, hydrochloride, [S-(R*,S*)]-

8.3 Other Safety Information

Chemical Assessment

IMAP assessments - 1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, hydrochloride, [S-(R*,S*)]-: Environment tier I assessment

IMAP assessments - 1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, hydrochloride, [S-(R*,S*)]-: Human health tier I assessment

9 Literature

9.1 Consolidated References

9.2 NLM Curated PubMed Citations

9.3 Springer Nature References

9.4 Chemical Co-Occurrences in Literature

9.5 Chemical-Gene Co-Occurrences in Literature

9.6 Chemical-Disease Co-Occurrences in Literature

10 Patents

10.1 Depositor-Supplied Patent Identifiers

10.2 WIPO PATENTSCOPE

10.3 Chemical Co-Occurrences in Patents

10.4 Chemical-Disease Co-Occurrences in Patents

10.5 Chemical-Gene Co-Occurrences in Patents

11 Biological Test Results

11.1 BioAssay Results

12 Classification

12.1 MeSH Tree

12.2 NCI Thesaurus Tree

12.3 ChEMBL Target Tree

12.4 UN GHS Classification

12.5 NORMAN Suspect List Exchange Classification

12.6 CCSBase Classification

12.7 EPA DSSTox Classification

12.8 MolGenie Organic Chemistry Ontology

13 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, hydrochloride, [S-(R*,S*)]-
    https://services.industrialchemicals.gov.au/search-assessments/
    1(3H)-Isobenzofuranone, 6,7-dimethoxy-3-(5,6,7,8-tetrahydro-4-methoxy-6-methyl-1,3-dioxolo[4,5-g]isoquinolin-5-yl)-, hydrochloride, [S-(R*,S*)]-
    https://services.industrialchemicals.gov.au/search-inventory/
  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. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  4. 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. 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
  6. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  7. 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
  8. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  9. 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
  10. 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
  11. Springer Nature
  12. Wikidata
  13. 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
  14. PubChem
  15. GHS Classification (UNECE)
  16. 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/
  17. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  18. PATENTSCOPE (WIPO)
CONTENTS