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6-Chloro-12-methyl-2-oxa-12,15-diazatetracyclo[7.5.3.01,10.03,8]heptadeca-3(8),4,6-trien-16-one

PubChem CID
3053755
Structure
6-Chloro-12-methyl-2-oxa-12,15-diazatetracyclo[7.5.3.01,10.03,8]heptadeca-3(8),4,6-trien-16-one_small.png
6-Chloro-12-methyl-2-oxa-12,15-diazatetracyclo[7.5.3.01,10.03,8]heptadeca-3(8),4,6-trien-16-one_3D_Structure.png
Molecular Formula
Synonyms
  • LORTALAMINE
  • 6-chloro-12-methyl-2-oxa-12,15-diazatetracyclo[7.5.3.01,10.03,8]heptadeca-3(8),4,6-trien-16-one
  • 70384-91-7
  • (+-)-(4aR*,10R*,10aS*)-8-Chloro-1,2,3,4,10,10a-hexahydro-2-methyl-4a,10-(iminoethano)-4aH-(1)benzopyrano(3,2-c)pyridin-12-one
  • (1S,9S,10S)-6-Chloro-12-methyl-2-oxa-12,15-diazatetracyclo[7.5.3.01,10.03,8]heptadeca-3(8),4,6-trien-16-one
Molecular Weight
292.76 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-08-09
  • Modify:
    2025-01-18
Description
6-chloro-12-methyl-2-oxa-12,15-diazatetracyclo[7.5.3.0~1,10~.0~3,8~]heptadeca-3,5,7-trien-16-one is a naphthyridine derivative.
Lortalamine (LM-1404) is a selective norepinephrine reuptake inhibitor developed in the 1980s. This drug never made it past clinical trials, likely due to ocular toxicity in animals, but has been used in positron emission tomography studies to label norepinephrine transporters.
LORTALAMINE is a small molecule drug with a maximum clinical trial phase of II.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
6-Chloro-12-methyl-2-oxa-12,15-diazatetracyclo[7.5.3.01,10.03,8]heptadeca-3(8),4,6-trien-16-one.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

6-chloro-12-methyl-2-oxa-12,15-diazatetracyclo[7.5.3.01,10.03,8]heptadeca-3(8),4,6-trien-16-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C15H17ClN2O2/c1-18-5-4-15-12(8-18)10(7-14(19)17-15)11-6-9(16)2-3-13(11)20-15/h2-3,6,10,12H,4-5,7-8H2,1H3,(H,17,19)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

CN1CCC23C(C1)C(CC(=O)N2)C4=C(O3)C=CC(=C4)Cl
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C15H17ClN2O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

70384-91-7

2.3.2 ChEBI ID

2.3.3 ChEMBL ID

2.3.4 DrugBank ID

2.3.5 HMDB ID

2.3.6 KEGG ID

2.3.7 Metabolomics Workbench ID

2.3.8 NCI Thesaurus Code

2.3.9 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • 4a-amino-8-chloro-2-methyl-1,2,3,4,4a,10a-hexahydro-10H-benzopyrano(3,2-c)pyridin-10-ylacetic acid lactam
  • LM 1404
  • LM-1404
  • lortalamine
  • lortalamine, (4aR,10R,10aR)-isomer

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
292.76 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
1.8
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
3
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
292.0978555 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
292.0978555 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
41.6 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
20
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
432
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
3
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)

5 Chemical Vendors

6 Literature

6.1 Consolidated References

6.2 NLM Curated PubMed Citations

6.3 Chemical Co-Occurrences in Literature

6.4 Chemical-Gene Co-Occurrences in Literature

6.5 Chemical-Disease Co-Occurrences in Literature

7 Interactions and Pathways

7.1 Drug-Drug Interactions

8 Classification

8.1 MeSH Tree

8.2 ChEBI Ontology

8.3 KEGG: Target-based Classification of Drugs

8.4 KEGG: Drug Groups

8.5 MolGenie Organic Chemistry Ontology

9 Information Sources

  1. ChEBI
    6-chloro-12-methyl-2-oxa-12,15-diazatetracyclo[7.5.3.0~1,10~.0~3,8~]heptadeca-3,5,7-trien-16-one
    https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:229896
  2. 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
  3. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  4. 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
  5. Human Metabolome Database (HMDB)
    LICENSE
    HMDB 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 (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
    (+-)-(4Ar*,10R*,10aS*)-8-Chloro-1,2,3,4,10,10a-hexahydro-2-methyl-4a,10-(iminoethano)-4aH-(1)benzopyrano(3,2-c)pyridin-12-one
    http://www.hmdb.ca/metabolites/HMDB0242234
  6. 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
    Target-based classification of drugs
    http://www.genome.jp/kegg-bin/get_htext?br08310.keg
  7. Metabolomics Workbench
  8. 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
  9. Wikipedia
  10. PubChem
  11. 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
  12. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS