Identification

Name
Levmetamfetamine
Accession Number
DB09571
Type
Small Molecule
Groups
Approved
Description

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

Structure
Thumb
Synonyms
  • Levmetamfetamine
  • Levomethamphetamine
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
1st Vaporizing InhalerLiquid50 mg/1NasalViny Health and Beauty Products Inc2015-12-012017-10-26Us
Amoray Vaporizing InhalerLiquid50 mg/1NasalMy Import Inc2015-09-292017-02-10Us
Nasal Decongestant InhalerInhalant50 mg/1NasalAphena Pharma Solutions2016-07-01Not applicableUs
Sinu InhalerInhalant50 mg/1NasalNeilMed2014-06-15Not applicableUs
Vapor InhalerInhalant50 mg/1NasalChain Drug Marketing Association, Inc.2014-01-01Not applicableUs
Vapor InhalerInhalant50 mg/1NasalWalgreens2016-07-01Not applicableUs
Vapor InhalerInhalant50 mg/1NasalCardinal Health (Leader)2014-03-01Not applicableUs
Vicks VapoInhalerInhalant0.245 mg/1000mgNasalProcter And Gamble2009-07-092013-06-01Us
Vicks Vapor InhalerInhalant0.245 mg/1000mgNasalProcter And Gamble1995-02-282009-07-09Us
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories
Not Available
UNII
Y24T9BT2Q2
CAS number
33817-09-3
Weight
Average: 149.237
Monoisotopic: 149.120449487
Chemical Formula
C10H15N
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

Pharmacology

Indication

Used over-the-counter for nasal congestion.

Associated Conditions
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,

Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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
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.
Not Available
Food Interactions
No interactions found.

References

General References
Not Available
External Links
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

Taxonomy

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
Amphetamine or derivatives / Phenylpropane / Aralkylamine / Secondary amine / Secondary aliphatic amine / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative / Organonitrogen compound / Amine
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not 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. [PubMed:3681889]
  2. UniProt [Link]
  3. ChEMBL [Link]

Drug created on November 30, 2015 13:27 / Updated on May 10, 2020 23:51

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