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Details

Stereochemistry RACEMIC
Molecular Formula C11H15NO2.ClH
Molecular Weight 229.703
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHOXYPHEDRINE HYDROCHLORIDE

SMILES

Cl.CNC(C)C(=O)C1=CC=C(OC)C=C1

InChI

InChIKey=QIJFAKGYWIXUDG-UHFFFAOYSA-N
InChI=1S/C11H15NO2.ClH/c1-8(12-2)11(13)9-4-6-10(14-3)7-5-9;/h4-8,12H,1-3H3;1H

HIDE SMILES / InChI

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/22922498 | https://www.ncbi.nlm.nih.gov/pubmed/27696217 | https://www.ncbi.nlm.nih.gov/pubmed/25438806

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.

Originator

Sources: Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen (1933), 66B, 858-66.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3860.0 nM [EC50]
12.5 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Two fatal intoxications with the new designer drug methedrone (4-methoxymethcathinone).
2010 Nov
Patents

Patents

Sample Use Guides

Oral dose between 100 to 200 mg
Route of Administration: Oral
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.
Name Type Language
METHOXYPHEDRINE HYDROCHLORIDE
WHO-DD  
Common Name English
PROPIOPHENONE, 4'-METHOXY-2-METHYLAMINO-, HYDROCHLORIDE
Systematic Name English
Methoxyphedrine hydrochloride [WHO-DD]
Common Name English
1-PROPANONE, 1-(4-METHOXYPHENYL)-2-(METHYLAMINO)-, HYDROCHLORIDE (1:1)
Systematic Name English
Code System Code Type Description
FDA UNII
4J1F13O4DC
Created by admin on Sat Dec 16 09:09:04 GMT 2023 , Edited by admin on Sat Dec 16 09:09:04 GMT 2023
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EVMPD
SUB03228MIG
Created by admin on Sat Dec 16 09:09:04 GMT 2023 , Edited by admin on Sat Dec 16 09:09:04 GMT 2023
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SMS_ID
100000085954
Created by admin on Sat Dec 16 09:09:04 GMT 2023 , Edited by admin on Sat Dec 16 09:09:04 GMT 2023
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EPA CompTox
DTXSID80681073
Created by admin on Sat Dec 16 09:09:04 GMT 2023 , Edited by admin on Sat Dec 16 09:09:04 GMT 2023
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PUBCHEM
52988262
Created by admin on Sat Dec 16 09:09:04 GMT 2023 , Edited by admin on Sat Dec 16 09:09:04 GMT 2023
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CAS
879665-92-6
Created by admin on Sat Dec 16 09:09:04 GMT 2023 , Edited by admin on Sat Dec 16 09:09:04 GMT 2023
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