Identification
- Generic Name
- DL-Methylephedrine
- DrugBank Accession Number
- DB11278
- Background
Methylephedrine is a sympathomimetic amine that appears in various over-the-counter cough and cold medications throughout the world 9, 10, 11. The abuse of methylephedrine-containing medications has been reported in Japan. Methylephedrine is not legally available in the United States, but has been identified in cases of drug abuse 7.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for DL-Methylephedrine (DB11278)
- Weight
- Average: 179.263
Monoisotopic: 179.131014171 - Chemical Formula
- C11H17NO
- Synonyms
- (+/-)-Methylephedrine
- (+/-)-N-methylephedrine
- Methylephedrine, (+/-)-
- Methylephedrine, DL-
- N-methylephedrine DL-form
Pharmacology
- Indication
Used as an antitussive and decongestant 5.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Symptomatic treatment of Fever ••• ••• Symptomatic treatment of Generalised muscle aches ••• ••• Symptomatic treatment of Headache ••• ••• Symptomatic treatment of Irritative cough ••• ••• Symptomatic treatment of Nasal congestion ••• ••• - Contraindications & Blackbox Warnings
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This drugs acts as an antitussive, bronchodilator, and adrenergic receptor agonist 5. It stimulates the alpha and beta adrenergic receptors, relieving cough and congestion 5.
As with other adrenomimetic amines, the drugs in this class are much less potent than norepinephrine itself. Members of this class of drugs increase both systolic and diastolic blood pressure, cardiac contractility, and cardiac output; in general, however, they do not increase heart rate. Bronchial smooth muscle relaxation of prolonged duration occurs, and pupils dilate 7.
- Mechanism of action
The pharmacology of methylephedrine is similar to that of other members of the ephedra alkaloid class of drugs. These compounds are sympathomimetic amines because they mimic the effects of the catecholamines on the sympathetic nervous system. These alkaloids permeate the blood-brain barrier and have a direct central nervous system stimulant effect with peripheral effects; the peripheral effects are indirect and primarily mediated by norepinephrine release 7.
Methylephedrine expands the bronchia by relaxing the bronchial muscles 15.
The decrease in urination with sympathomimetic use is increased through activation of the alpha-adrenoceptors of the smooth muscles of the bladder 15.
Target Actions Organism ABeta-1 adrenergic receptor agonistHumans AAlpha-2A adrenergic receptor agonistHumans AAlpha adrenergic receptor agonistHumans ABeta adrenergic receptor agonistHumans - Absorption
Methylephedrine is rapidly absorbed following oral administration 7. Peak plasma concentrations of ephedrine (from which methylephedrine is derived) occur 2-3h after administration 3. Due to the fact that methylephedrine is a derivative of ephedrine 12, peak plasma concentrations are likely similar.
- Volume of distribution
Ephedrine: 2.5-3.0 L/kg 3. Methylephedrine is a derivative of ephedrine 12 and quickly distributed throughout the body 15.
- Protein binding
Not Available
- Metabolism
Methylephedrine is metabolized to give ephedrine and norephedrine 15.
- Route of elimination
The primary compound excreted in urine is unchanged methylephedrine (33-40% of dose), followed by the metabolite methylephedrine-N-oxide (15% of dose), and approximately 8% of the dose excreted as ephedrine after 24 hours. About 70% of the dose is excreted in the urine as metabolites over 72 hours 7.
Alkaline urine reduces elimination to 20-35% of the dose 15.
- Half-life
3-6 hours (Ephedrine) 15.
- Clearance
Not Available
- Adverse Effects
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Ld50 mouse (intraperitoneal): 185mg/kg 6.
Sympathomimetic drugs, such as DL-methylphedrine, can lead to an increase in catecholamines, resulting in a variety of effects 2, 13:
Nervous System/CNS/Psychiatric
Insomnia, Headaches, Seizure, Cerebrovascular Accident, Nervousness, Tremor or other motor disturbance, Psychosis with long-term, chronic use 15
Cardiovascular System Hypertension, Cardiac arrhythmia, Myocardial Infarction, Hypersensitivity Myocarditis
Renal System Nephrolithiasis
General Predisposition to Heat Exhaustion and Heat Stroke, Hyperglycemia, Glaucoma
The Japanese Ministry of Health made a statement in July 2017 that preparations containing this drug should not be used in children younger than 12 years old (who are highly susceptible to respiratory depression. Overseas, there have been reports that the risk of serious respiratory depression, including death, is high in children younger than 12 years old) 14.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of DL-Methylephedrine which could result in a higher serum level. Acebutolol The therapeutic efficacy of DL-Methylephedrine can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Aceclofenac is combined with DL-Methylephedrine. Acemetacin The risk or severity of hypertension can be increased when DL-Methylephedrine is combined with Acemetacin. Acetazolamide Acetazolamide may increase the excretion rate of DL-Methylephedrine which could result in a lower serum level and potentially a reduction in efficacy. - 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.- Product Ingredients
Ingredient UNII CAS InChI Key DL-Methylephedrine hydrochloride 99214P83XM 18760-80-0 NTCYWJCEOILKNG-ROLPUNSJSA-N - International/Other Brands
- DL-Methylephedrine HCl (Fu Yuan) / dl-Methylephedrine Hydrochloride 10% Maruishi (Maruishi Pharmaceuticals) / dl-Methylephedrine Hydrochloride 10% Metal (Nakakita Yakuhin, Japan) / dl-Methylephedrine Hydrochloride 10% Sankei (Sankei Seiyaku) / dl-Methylephedrine Hydrochloride 10% Sanwa (Sanwa Kagaku) / Methy F (Tanabe Mitsubishi Pharma) / Methylephedrine 10% Fuso (Fuso Pharmaceutical) / Methylhoedrin 10% (Mylan Seiyaku) / Tabellae DL-Methyl (Ying Yuan)
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Facol Classic One DL-Methylephedrine hydrochloride (12.5 mg/1) + Acetaminophen (200 mg/1) + Chlorpheniramine maleate (1.25 mg/1) + Cloperastine hydrochloride (8 mg/1) + Guaifenesin (41.6 mg/1) + Pseudoephedrine hydrochloride (15 mg/1) Capsule Oral OASIS TRADING 2018-11-22 Not applicable US 
Pancold S DL-Methylephedrine hydrochloride (17.5 mg/30mL) + Acetaminophen (300 mg/30mL) + Caffeine (30 mg/30mL) + Chlorpheniramine (2.5 mg/30mL) + Guaifenesin (83.3 mg/30mL) Liquid Oral Kafus Co., Ltd 2013-01-15 Not applicable US Whituben DL-Methylephedrine hydrochloride (12.5 mg/1) + Acetaminophen (180 mg/1) + Dextromethorphan hydrobromide monohydrate (8 mg/1) + Guaifenesin (20.84 mg/1) + Pseudoephedrine hydrochloride (15 mg/1) + Triprolidine hydrochloride monohydrate (0.66 mg/1) Capsule Oral OASIS TRADING 2018-11-22 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Facol Classic One DL-Methylephedrine hydrochloride (12.5 mg/1) + Acetaminophen (200 mg/1) + Chlorpheniramine maleate (1.25 mg/1) + Cloperastine hydrochloride (8 mg/1) + Guaifenesin (41.6 mg/1) + Pseudoephedrine hydrochloride (15 mg/1) Capsule Oral OASIS TRADING 2018-11-22 Not applicable US Whituben DL-Methylephedrine hydrochloride (12.5 mg/1) + Acetaminophen (180 mg/1) + Dextromethorphan hydrobromide monohydrate (8 mg/1) + Guaifenesin (20.84 mg/1) + Pseudoephedrine hydrochloride (15 mg/1) + Triprolidine hydrochloride monohydrate (0.66 mg/1) Capsule Oral OASIS TRADING 2018-11-22 Not applicable US
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Phenylpropanes
- Direct Parent
- Phenylpropanes
- Alternative Parents
- Aralkylamines / Trialkylamines / Secondary alcohols / 1,2-aminoalcohols / Organopnictogen compounds / Hydrocarbon derivatives / Aromatic alcohols
- Substituents
- 1,2-aminoalcohol / Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic homomonocyclic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound / Organonitrogen compound
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- SHS9PGQ2LS
- CAS number
- 1201-56-5
- InChI Key
- FMCGSUUBYTWNDP-ONGXEEELSA-N
- InChI
- InChI=1S/C11H17NO/c1-9(12(2)3)11(13)10-7-5-4-6-8-10/h4-9,11,13H,1-3H3/t9-,11-/m0/s1
- IUPAC Name
- (1R,2S)-2-(dimethylamino)-1-phenylpropan-1-ol
- SMILES
- C[C@@H]([C@H](O)C1=CC=CC=C1)N(C)C
References
- General References
- Inoue T, Suzuki S: The metabolism of (+-)-methylephedrine in rat and man. Xenobiotica. 1990 Jan;20(1):99-106. doi: 10.3109/00498259009046816. [Article]
- Dunnick JK, Kissling G, Gerken DK, Vallant MA, Nyska A: Cardiotoxicity of Ma Huang/caffeine or ephedrine/caffeine in a rodent model system. Toxicol Pathol. 2007 Aug;35(5):657-64. doi: 10.1080/01926230701459978. [Article]
- Steven B. Karch, Olaf Drummer (1996). Karch's Pathology of Drug Abuse, Third Edition. CRC Press.
- DL-Methylphedrine Hydrochloride [Link]
- Methylphedrine, DL, Drugs.com [Link]
- NIH Toxnet, DL Methylphedrine [Link]
- Methylphedrine concentrations in drug ad urine specimens [Link]
- Genome. JP DL-methylphedrine [Link]
- Daily Med, Pancold S [Link]
- Chlorphenamine/Dihydrocodeine/Guaifenesin/Methylephedrine/dl Uses More: https://www.ndrugs.com/?s=chlorphenamine/dihydrocodeine/guaifenesin/methylephedrine/dl More: https://www.ndrugs.com/?s=chlorphenamine/dihydrocodeine/guaifenesin/methylephedrine/dl [Link]
- Tossamin Plus [Link]
- Methylphedrine, PubChem [Link]
- Family Practice Notebook: Sympathomimetics [Link]
- Revision of Precautions Dihydrocodeine phosphate/ dl-Methylephedrine hydrochloride/ Chlorpheniramine maleate [File]
- 4-Methylephedrine, EUA [File]
- External Links
- ChemSpider
- 58315
- 1546444
- ChEBI
- 113556
- ChEMBL
- CHEMBL445001
- ZINC
- ZINC000000000491
- Wikipedia
- Methylephedrine
- MSDS
- Download (68.6 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule Oral Liquid Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 208 MSDS boiling point (°C) 251.3 https://www.chemsrc.com/en/cas/18760-80-0_1189835.html logP 2.47 https://www.chemsrc.com/en/cas/18760-80-0_1189835.html - Predicted Properties
Property Value Source Water Solubility 15.4 mg/mL ALOGPS logP 1.73 ALOGPS logP 1.7 Chemaxon logS -1.1 ALOGPS pKa (Strongest Acidic) 13.88 Chemaxon pKa (Strongest Basic) 8.86 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 23.47 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 54.98 m3·mol-1 Chemaxon Polarizability 20.55 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-03xr-1900000000-111e0086f39519af7616 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-4900000000-642b74a51997f8172813 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00fr-9400000000-365b1998fae560569153 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-01b9-7900000000-bf01cd9eddbd8896c391 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-00ou-9400000000-a25d2062f5982122e0b0 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-056r-9700000000-37bdf87b8b6d8ebe0c4d Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 143.7717364 predictedDarkChem Lite v0.1.0 [M-H]- 144.99858 predictedDeepCCS 1.0 (2019) [M+H]+ 144.0802364 predictedDarkChem Lite v0.1.0 [M+H]+ 147.39418 predictedDeepCCS 1.0 (2019) [M+Na]+ 153.30669 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Receptor signaling protein activity
- Specific Function
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
- Gene Name
- ADRB1
- Uniprot ID
- P08588
- Uniprot Name
- Beta-1 adrenergic receptor
- Molecular Weight
- 51322.1 Da
References
- Genome. JP DL-methylphedrine [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Thioesterase binding
- Specific Function
- Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
- Gene Name
- ADRA2A
- Uniprot ID
- P08913
- Uniprot Name
- Alpha-2A adrenergic receptor
- Molecular Weight
- 48956.275 Da
References
- Genome. JP DL-methylphedrine [Link]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Protein heterodimerization activity
- Specific Function
- This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Components:
References
- Genome. JP DL-methylphedrine [Link]
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- General Function
- Receptor signaling protein activity
- Specific Function
- Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately e...
Components:
| Name | UniProt ID |
|---|---|
| Beta-1 adrenergic receptor | P08588 |
| Beta-2 adrenergic receptor | P07550 |
| Beta-3 adrenergic receptor | P13945 |
References
- Genome. JP DL-methylphedrine [Link]
Drug created at December 03, 2015 16:52 / Updated at September 28, 2021 21:54