Levmetamfetamine

Identification

Generic Name
Levmetamfetamine
DrugBank Accession Number
DB09571
Background

Levomethamphetamine, the L-enantiomer of methamphetamine is a sympathomimetic vasoconstrictor used in some over-the-counter (OTC) nasal decongestant inhalers in the United States.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 149.237
Monoisotopic: 149.120449487
Chemical Formula
C10H15N
Synonyms
  • Levmetamfetamine
  • Levomethamphetamine

Pharmacology

Indication

Used over-the-counter for nasal congestion.

Pharmacology
Accelerate your drug discovery research with the industry’s only fully connected ADMET dataset, ideal for:
Machine Learning
Data Science
Drug Discovery
Accelerate your drug discovery research with our fully connected ADMET dataset
Learn more
Associated Conditions
Contraindications & Blackbox Warnings
Contraindications
Contraindications & Blackbox Warnings
With our commercial data, access important information on dangerous risks, contraindications, and adverse effects.
Learn more
Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects
Learn more
Pharmacodynamics

Levomethamphetamine increases norepinephrine release resulting in increased vasocontriction.

Mechanism of action

Levomethamphetamine crosses the blood-brain-barrier and acts as a TAAR1 agonist,[3] functioning as a selective norepinephrine releasing agent in the central nervous system,

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

The elimination half-life of levomethamphetamine is between 13.3 and 15 hours.

Clearance

Not Available

Adverse Effects
Medicalerrors
Reduce medical errors
and improve treatment outcomes with our comprehensive & structured data on drug adverse effects.
Learn more
Reduce medical errors & improve treatment outcomes with our adverse effects data
Learn more
Toxicity

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.
Not Available
Food Interactions
No interactions found.

Products

Products
Comprehensive & structured drug product info
From application numbers to product codes, connect different identifiers through our commercial datasets.
Learn more
Easily connect various identifiers back to our datasets
Learn more
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
1st Vaporizing InhalerLiquid50 mg/1NasalViny Health and Beauty Products Inc2015-12-012017-10-26US flag
Amoray Vaporizing InhalerLiquid50 mg/1NasalMy Import Inc2015-09-292017-02-10US flag
Nasal Decongestant InhalerInhalant50 mg/1NasalAphena Pharma Solutions2016-07-01Not applicableUS flag
Sinu InhalerInhalant50 mg/1NasalNeilMed Pharmaceuticals, Inc.2014-06-15Not applicableUS flag
Vapor InhalerInhalant50 mg/1NasalWalgreens2016-07-01Not applicableUS flag
Vapor InhalerInhalant50 mg/1NasalC.D.M.A., Inc.2014-01-01Not applicableUS flag
Vapor InhalerInhalant50 mg/1NasalCardinal Health (Leader)2014-03-01Not applicableUS flag
Vapor Inhaler levmetamfetamine nasal decongestant, Best ChoiceInhalant50 mg/1NasalValu Merchandisers Company2021-02-24Not applicableUS flag
Vapor Inhaler levmetamfetamine nasal decongestant, DG healthInhalant50 mg/1NasalDolgencorp Inc.2021-02-23Not applicableUS flag
Vapor Inhaler levmetamfetamine nasal decongestant, EqualineInhalant50 mg/1NasalSUPERVALU INC.2021-02-24Not applicableUS flag

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenethylamines
Direct Parent
Amphetamines and derivatives
Alternative Parents
Phenylpropanes / Aralkylamines / Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Amine / Amphetamine or derivatives / Aralkylamine / Aromatic homomonocyclic compound / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Phenylpropane / Secondary aliphatic amine
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Y24T9BT2Q2
CAS number
33817-09-3
InChI Key
MYWUZJCMWCOHBA-SECBINFHSA-N
InChI
InChI=1S/C10H15N/c1-9(11-2)8-10-6-4-3-5-7-10/h3-7,9,11H,8H2,1-2H3/t9-/m1/s1
IUPAC Name
methyl[(2R)-1-phenylpropan-2-yl]amine
SMILES
CN[C@H](C)CC1=CC=CC=C1

References

General References
Not Available
PubChem Compound
36604
PubChem Substance
347827882
ChemSpider
33634
BindingDB
50359500
RxNav
1314416
ChEBI
136013
ChEMBL
CHEMBL1927030
ZINC
ZINC000008466459
Wikipedia
Levomethamphetamine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedDiagnosticHealthy Volunteers / Opioids1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
LiquidNasal50 mg/1
InhalantNasal50 mg/1
InhalantNasal0.245 mg/1000mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.928 mg/mLALOGPS
logP2.23ALOGPS
logP2.24ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)10.21ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity48.48 m3·mol-1ChemAxon
Polarizability18.09 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
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
GC-MS Spectrum - CI-BGC-MSsplash10-0udi-0900000000-8d39b849b8598c565a33
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

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Ligand
General Function
Phenylethanolamine n-methyltransferase activity
Specific Function
Converts noradrenaline to adrenaline.
Gene Name
PNMT
Uniprot ID
P11086
Uniprot Name
Phenylethanolamine N-methyltransferase
Molecular Weight
30854.745 Da
References
  1. Grunewald GL, Markovich KM, Sall DJ: Binding orientation of amphetamine and norfenfluramine analogues in the benzonorbornene and benzobicyclo[3.2.1]octane ring systems at the active site of phenylethanolamine N-methyltransferase (PNMT) J Med Chem. 1987 Dec;30(12):2191-208. doi: 10.1021/jm00395a005. [Article]
  2. UniProt [Link]
  3. ChEMBL [Link]

Drug created on November 30, 2015 20:27 / Updated on February 21, 2021 18:52