| Stereochemistry | RACEMIC |
| Molecular Formula | C11H15NO2 |
| Molecular Weight | 193.2423 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CNC(C)C(=O)C1=CC=C(OC)C=C1
InChI
InChIKey=MQUIHBQDYYAEMH-UHFFFAOYSA-N
InChI=1S/C11H15NO2/c1-8(12-2)11(13)9-4-6-10(14-3)7-5-9/h4-8,12H,1-3H3
| Molecular Formula | C11H15NO2 |
| Molecular Weight | 193.2423 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
Methoxyphedrine (para-methoxymethcathinone, 4-methoxymethcathinone, bk-PMMA, PMMC, Methedrone, 4-MeOMC) is a phenethylamine, amphetamine, and cathinone derivative that acts as a triple reuptake/release/reversible monoamine oxidase inhibitor and used as a recreational drug. Methedrone has been found to be a potent serotonin transporter (SERT) and norepinephrine transporter (NET) inhibitor, but a weak dopamine transporter (DAT) inhibitor. Methedrone induces the transportation mediated release of NE, DA, and 5-HT from cells preloaded with monoamines making it a serotonin-norepinephrine-dopamine (SNDRA) releasing agent, also known as triple releasing agent (TRA), which is a common characteristic among drugs of abuse. The health risks associated with Methedrone are unknown but are expected to be similar to other cathinones. The deaths of two young men in southeast Sweden in 2009 were attributed to Methedrone overdose.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 3860.0 nM [EC50] | |||
| 12.5 nM [EC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
Patents
Sample Use Guides
Rat synaptosomes were used for activity evaluation. Synaptosomes were preloaded with radiolabeled substrate in Krebs-phosphate buffer for 1 h (steady state). For release assays, 9 nM [3H]1-methyl-4-phenylpyridinium ( [3H]MPP+) was used as the radiolabeled substrate for DAT, whereas 5 nM [3H]5-HT was used as a substrate for SERT. All buffers used in the release assay methods contained 1 μM reserpine to block vesicular uptake of substrates. Release assays were initiated by adding 850 μL of preloaded synaptosomes to 150 μL of test drug (Methoxyphedrine). Release was terminated by vacuum filtration, and retained radioactivity was quantified by liquid scintillation counting. Effects of test drug concentrations were expressed as percentage of maximum release, with maximum release (i.e. 100% Emax) was defined as the release produced by 10 nM tyramine for DAT and NET assay conditions, and 100 nM tyramine for SERT assay conditions.
