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
Structure for Levmetamfetamine (DB09571)
- Weight
- Average: 149.237
Monoisotopic: 149.120449487 - Chemical Formula
- C10H15N
- Synonyms
- Levmetamfetamine
- Levomethamphetamine
Pharmacology
- Indication
Used over-the-counter for nasal congestion.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Symptomatic treatment of Nasal congestion ••• ••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image 1st Vaporizing Inhaler Liquid 50 mg/1 Nasal Viny Health and Beauty Products Inc 2015-12-01 2017-10-26 US 
Amoray Vaporizing Inhaler Liquid 50 mg/1 Nasal My Import Inc 2015-09-29 2017-02-10 US Levmetamfetamine Inhalant 50 mg/1 Nasal MEIJER, INC. 2023-09-29 Not applicable US Nasal Decongestant Inhaler Inhalant 50 mg/1 Nasal Aphena Pharma Solutions 2016-07-01 Not applicable US Sinu Inhaler Inhalant 50 mg/1 Nasal NeilMed Pharmaceuticals, Inc. 2014-06-15 Not applicable US
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
- External Links
- PubChem Compound
- 36604
- PubChem Substance
- 347827882
- ChemSpider
- 33634
- BindingDB
- 50359500
- 1314416
- ChEBI
- 136013
- ChEMBL
- CHEMBL1927030
- ZINC
- ZINC000008466459
- Wikipedia
- Levomethamphetamine
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 1 Completed Diagnostic Healthy Volunteers (HV) / Opioids 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Liquid Nasal 50 mg/1 Inhalant Nasal 50 mg/1 Inhalant Nasal 0.245 mg/1000mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.928 mg/mL ALOGPS logP 2.23 ALOGPS logP 2.24 Chemaxon logS -2.2 ALOGPS pKa (Strongest Basic) 10.21 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 12.03 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 48.48 m3·mol-1 Chemaxon Polarizability 18.09 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 138.2538095 predictedDarkChem Lite v0.1.0 [M-H]- 132.01935 predictedDeepCCS 1.0 (2019) [M+H]+ 139.1116095 predictedDarkChem Lite v0.1.0 [M+H]+ 134.91405 predictedDeepCCS 1.0 (2019) [M+Na]+ 138.6046095 predictedDarkChem Lite v0.1.0 [M+Na]+ 143.96394 predictedDeepCCS 1.0 (2019)
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
- 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]
- UniProt [Link]
- ChEMBL [Link]
Drug created at November 30, 2015 20:27 / Updated at September 28, 2021 21:54