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
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.
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
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)
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)
MJRPHRMGEKCADU-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)
CN1CCC23C(C1)C(CC(=O)N2)C4=C(O3)C=CC(=C4)Cl
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)
C15H17ClN2O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)
70384-91-7
- 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
- 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
- Lortalamina
- LM-1404
- Lortalamine (USAN/INN)
- CHEMBL2218922
- CHEBI:229896
- DB09187
- D04781
- 4a-amino-8-chloro-2-methyl-1,2,3,4,4a,10a-hexahydro-10H-benzopyrano(3,2-c)pyridin-10-ylacetic acid lactam
- 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
Property Name
Property Value
Reference
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)
Follow these links to do a live 2D search or do a live 3D search for this compound, sorted by annotation score. This section is deprecated (see here for details), but these live search links provide equivalent functionality to the table that was previously shown here.
Same Connectivity Count
Same Isotope Count
Same Parent, Connectivity Count
Same Parent, Isotope Count
Same Parent, Exact Count
Mixtures, Components, and Neutralized Forms Count
Similar Compounds (2D)
Similar Conformers (3D)
- ChEBI6-chloro-12-methyl-2-oxa-12,15-diazatetracyclo[7.5.3.0~1,10~.0~3,8~]heptadeca-3,5,7-trien-16-onehttps://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:229896
- DrugBankLICENSECreative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)https://www.drugbank.ca/legal/terms_of_useLortalaminehttps://www.drugbank.ca/drugs/DB09187
- Open TargetsLICENSEDatasets generated by the Open Targets Platform are freely available for download.https://platform-docs.opentargets.org/licence
- ChEMBLLICENSEAccess 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
- Human Metabolome Database (HMDB)LICENSEHMDB 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-onehttp://www.hmdb.ca/metabolites/HMDB0242234
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.htmlTarget-based classification of drugshttp://www.genome.jp/kegg-bin/get_htext?br08310.keg
- Metabolomics Workbench
- NCI Thesaurus (NCIt)LICENSEUnless 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
- WikipediaLortalaminehttps://en.wikipedia.org/wiki/Lortalamine
- PubChem
- Medical Subject Headings (MeSH)LICENSEWorks 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.htmllortalaminehttps://www.ncbi.nlm.nih.gov/mesh/67031101
- MolGenieMolGenie Organic Chemistry Ontologyhttps://github.com/MolGenie/ontology/
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