Lortalamine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Lortalamine
Accession Number
DB09187
Type
Small Molecule
Groups
Experimental
Description

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.

Structure
Thumb
Synonyms
Not Available
External IDs
LM-1404
Categories
UNII
9GIR4SV22T
CAS number
70384-91-7
Weight
Average: 292.76
Monoisotopic: 292.0978555
Chemical Formula
C15H17ClN2O2
InChI Key
MJRPHRMGEKCADU-UHFFFAOYSA-N
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)
IUPAC Name
6-chloro-12-methyl-2-oxa-12,15-diazatetracyclo[7.5.3.0¹,¹⁰.0³,⁸]heptadeca-3,5,7-trien-16-one
SMILES
CN1CCC23NC(=O)CC(C2C1)C1=CC(Cl)=CC=C1O3

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe risk or severity of adverse effects can be increased when Lortalamine is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of adverse effects can be increased when Lortalamine is combined with (S)-Warfarin.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Lortalamine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with Lortalamine.
4-hydroxycoumarinThe risk or severity of adverse effects can be increased when Lortalamine is combined with 4-hydroxycoumarin.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with Lortalamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Lortalamine is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when 7-Nitroindazole is combined with Lortalamine.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Lortalamine.
AcenocoumarolThe risk or severity of adverse effects can be increased when Lortalamine is combined with Acenocoumarol.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
  1. Belleville M, Grand M, Briet P: Plasma levels, elimination and metabolic fate of 4a-amino-8-chloro-2-methyl-1,2,3,4,4a,10a-hexahydro-10H-benzopyrano[3,2-c]pyridin -10-ylacetic acid lactam, a new antidepressive agent, in rats and dogs. Drug Metab Dispos. 1981 May-Jun;9(3):233-9. [PubMed:6113932]
  2. Depin JC, Betbeder-Matibet A, Bonhomme Y, Muller AJ, Berthelon JJ: Pharmacology of lortalamine, a new potent non-tricyclic antidepressant. Arzneimittelforschung. 1985;35(11):1655-62. [PubMed:4091869]
  3. Lin KS, Ding YS: Synthesis and C-11 labeling of three potent norepinephrine transporter selective ligands ((R)-nisoxetine, lortalamine, and oxaprotiline) for comparative PET studies in baboons. Bioorg Med Chem. 2005 Aug 1;13(15):4658-66. [PubMed:15914010]
  4. Elsom LF, Biggs SR, Chasseaud LF, Hawkins DR, Pulsford J, Darragh A: Metabolism of the anti-depressant lortalamine. Eur J Drug Metab Pharmacokinet. 1985 Jul-Sep;10(3):209-15. [PubMed:4085522]
  5. Mally C, Thiebault JJ: Ocular toxicity in beagle dogs with lortalamine, a non tricyclic antidepressant compound. Drug Chem Toxicol. 1990;13(4):309-23. [PubMed:2279460]
  6. Ding YS, Lin KS, Logan J, Benveniste H, Carter P: Comparative evaluation of positron emission tomography radiotracers for imaging the norepinephrine transporter: (S,S) and (R,R) enantiomers of reboxetine analogs ([11C]methylreboxetine, 3-Cl-[11C]methylreboxetine and [18F]fluororeboxetine), (R)-[11C]nisoxetine, [11C]oxaprotiline and [11C]lortalamine. J Neurochem. 2005 Jul;94(2):337-51. [PubMed:15998285]
  7. Ding YS, Lin KS, Logan J: PET imaging of norepinephrine transporters. Curr Pharm Des. 2006;12(30):3831-45. [PubMed:17073682]
External Links
KEGG Drug
D04781
PubChem Compound
3053755
PubChem Substance
310265095
ChemSpider
2315437
ChEMBL
CHEMBL2218922
Wikipedia
Lortalamine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.654 mg/mLALOGPS
logP1.93ALOGPS
logP1.9ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)10.2ChemAxon
pKa (Strongest Basic)8.28ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.57 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity75.95 m3·mol-1ChemAxon
Polarizability30.05 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as naphthyridines. These are compounds containing a naphthyridine moiety, a naphthalene in which a carbon atom has been replaced by a nitrogen in each of the two rings. The naphthyridine skeleton can also be described as an assembly two fused pyridine rings, which do not share their nitrogen atom.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazanaphthalenes
Sub Class
Naphthyridines
Direct Parent
Naphthyridines
Alternative Parents
1-benzopyrans / Piperidinones / Aralkylamines / Delta lactams / Aryl chlorides / Benzenoids / Trialkylamines / Secondary carboxylic acid amides / Amino acids and derivatives / Oxacyclic compounds
show 6 more
Substituents
Chromane / Benzopyran / Naphthyridine / 1-benzopyran / Delta-lactam / Aralkylamine / Piperidinone / Aryl chloride / Aryl halide / Piperidine
show 22 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Drug created on October 16, 2015 13:41 / Updated on September 02, 2019 19:07