General
Preferred name
DL-Methylephedrine
Synonyms
N-METHYL (-)EPHEDRINE [1R,2S] ()
methylephedrine ()
{-}-N-METHYLEPHEDRINE ()
P&D ID
PD000062
CAS
552-79-4
Tags
natural product
drug
available
Drug Status
approved
Probe control
Probe control not defined
Orthogonal probes
0
No orthogonal probes found
Similar probes
0
No structurally similar probes found
Structure
P&D probe-likeness score
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
TOXICITY
Ld50 mouse (intraperitoneal): 185mg/kg [L2835].; ; Sympathomimetic drugs, such as DL-methylphedrine, can lead to an increase in catecholamines, resulting in a variety of effects [A33132], [L2848]:; ; **Nervous System/CNS/Psychiatric**; ; Insomnia, Headaches, Seizure, Cerebrovascular Accident, Nervousness, Tremor or other motor disturbance, Psychosis with long-term, chronic use [F100]; ; **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) [F98].
ROE
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 [L2836].; ; Alkaline urine reduces elimination to 20-35% of the dose [F100].
MOA
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 [L2836]. ; ; Methylephedrine expands the bronchia by relaxing the bronchial muscles [F100].; ; The decrease in urination with sympathomimetic use is increased through activation of the alpha-adrenoceptors of the smooth muscles of the bladder [F100].
PHARMACODYNAMICS
This drugs acts as an antitussive, bronchodilator, and adrenergic receptor agonist [L2834]. It stimulates the alpha and beta adrenergic receptors, relieving cough and congestion [L2834].; ; 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 [L2836].
[[ p.pathway_name ]]
[[ compound.targets[tid].gene_name ]]
Compound Sets
7
[[ a.name ]]
[[ ligand_id ]]
free of charge
External IDs
23
Molecular Weight
179.13
Hydrogen Bond Acceptors
2
Hydrogen Bond Donors
1
Rotatable Bonds
3
Ring Count
1
Aromatic Ring Count
1
cLogP
1.67
TPSA
23.47
Fraction CSP3
0.45
Chiral centers
2.0
Largest ring
6.0
QED
0.76
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Source data
