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Details

Stereochemistry RACEMIC
Molecular Formula C11H15NO
Molecular Weight 177.2429
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEPHEDRONE

SMILES

CNC(C)C(=O)C1=CC=C(C)C=C1

InChI

InChIKey=YELGFTGWJGBAQU-UHFFFAOYSA-N
InChI=1S/C11H15NO/c1-8-4-6-10(7-5-8)11(13)9(2)12-3/h4-7,9,12H,1-3H3

HIDE SMILES / InChI

Molecular Formula C11H15NO
Molecular Weight 177.2429
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Mephedrone (4-methylmethcathinone) is a β-ketoamphetamine belonging to the family of synthetic cathinones, an emerging class of designer drugs known for their hallucinogenic and psychostimulant properties as well as for their abuse potential. Mephedrone is a stimulant of dopamine (DA) release and blocks its reuptake through its interaction with the dopamine transporter. Furthermore, it has some affinity for various 5-hydroxytryptamine (5-HT) receptor subtypes. Neurotoxic effect of mephedrone on 5-HT and DA systems remains controversial. Although some studies in animal models reported no damage to DA nerve endings in the striatum and no significant changes in brain monoamine levels, some others suggested a rapid reduction in 5-HT and DA transporter function. Persistent serotonergic deficits were observed after binge like treatment in a warm environment and in both serotonergic and dopaminergic nerve endings at high ambient temperature. Oxidative stress cytotoxicity and an increase in frontal cortex lipid peroxidation were also reported. Despite the re-classification of mephedrone as a Class B restricted substance by the United Kingdom and restrictive legislation by the United States, international policy regarding mephedrone control is still developing and interest in synthetic amphetamine-like drugs could drive the development of future mephedrone analogues.

Approval Year

PubMed

PubMed

TitleDatePubMed
[Smoking by people addicted to drugs].
2010
Multiple-drug toxicity caused by the coadministration of 4-methylmethcathinone (mephedrone) and heroin.
2010 Apr
A harmless high?
2010 Aug 28
Headshop heartache: acute mephedrone 'meow' myocarditis.
2010 Dec
Beta-keto amphetamines: studies on the metabolism of the designer drug mephedrone and toxicological detection of mephedrone, butylone, and methylone in urine using gas chromatography-mass spectrometry.
2010 Jun
Metabolism of designer drugs of abuse: an updated review.
2010 Jun 1
Britain moves to curtail new drug craze.
2010 Jun 15
Mephedrone is an amphetamine "by another name," drug adviser tells MPs.
2010 Mar 24
Home secretary bans mephedrone after taking advice from depleted council.
2010 Mar 31
Head shop compound abuse amongst attendees of the Drug Treatment Centre Board.
2010 May
Case series of individuals with analytically confirmed acute mephedrone toxicity.
2010 Nov
Mephedrone use and associated adverse effects in school and college/university students before the UK legislation change.
2010 Nov
Dependence and psychosis with 4-methylmethcathinone (mephedrone) use.
2010 Nov 3
Mephedrone: still available and twice the price.
2010 Nov 6
Methaemoglobinaemia due to mephedrone ('snow').
2010 Oct 22
Recreational use of mephedrone (4-methylmethcathinone, 4-MMC) with associated sympathomimetic toxicity.
2010 Sep
The serotonin syndrome as a result of mephedrone toxicity.
2010 Sep 20
Mephedrone (4-methylmethcathinone)-related deaths.
2011 Apr
Clinical pattern of toxicity associated with the novel synthetic cathinone mephedrone.
2011 Apr
Clinical characteristics of mephedrone toxicity reported to the U.K. National Poisons Information Service.
2011 Aug
[Mephedrone -- an old-new drug of abuse].
2011 Jul 24
A case of extreme agitation and death after the use of mephedrone in The Netherlands.
2011 Mar 20
Emergency department visits after use of a drug sold as "bath salts"--Michigan, November 13, 2010-March 31, 2011.
2011 May 20
Mephedrone: use, subjective effects and health risks.
2011 Nov
Instability of the ecstasy market and a new kid on the block: mephedrone.
2011 Nov
Neuronal changes and oxidative stress in adolescent rats after repeated exposure to mephedrone.
2015 Jul 1
Patents
Substance Class Chemical
Created
by admin
on Thu Jul 06 06:49:38 UTC 2023
Edited
by admin
on Thu Jul 06 06:49:38 UTC 2023
Record UNII
8BA8T27317
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MEPHEDRONE
Common Name English
4-METHYLMETHCATHINONE
Common Name English
4-METHYLEPHEDRONE
Common Name English
M-CAT
Common Name English
BATH SALTS COMPONENT MEPHEDRONE
Common Name English
J2.756.280I
Code English
MEOW MEOW
Common Name English
2-METHYLAMINO-1-P-TOLYLPROPANE-1-ONE
Common Name English
1-PROPANONE, 2-(METHYLAMINO)-1-(4-METHYLPHENYL)-
Systematic Name English
4-MMC
Common Name English
Classification Tree Code System Code
DEA NO. 1248
Created by admin on Thu Jul 06 06:49:38 UTC 2023 , Edited by admin on Thu Jul 06 06:49:38 UTC 2023
WIKIPEDIA Designer-drugs-4-Methylmethcathinone
Created by admin on Thu Jul 06 06:49:38 UTC 2023 , Edited by admin on Thu Jul 06 06:49:38 UTC 2023
Code System Code Type Description
PUBCHEM
45266826
Created by admin on Thu Jul 06 06:49:38 UTC 2023 , Edited by admin on Thu Jul 06 06:49:38 UTC 2023
PRIMARY
EPA CompTox
DTXSID20891437
Created by admin on Thu Jul 06 06:49:38 UTC 2023 , Edited by admin on Thu Jul 06 06:49:38 UTC 2023
PRIMARY
HSDB
7979
Created by admin on Thu Jul 06 06:49:38 UTC 2023 , Edited by admin on Thu Jul 06 06:49:38 UTC 2023
PRIMARY
EVMPD
SUB32114
Created by admin on Thu Jul 06 06:49:38 UTC 2023 , Edited by admin on Thu Jul 06 06:49:38 UTC 2023
PRIMARY
MESH
C548233
Created by admin on Thu Jul 06 06:49:38 UTC 2023 , Edited by admin on Thu Jul 06 06:49:38 UTC 2023
PRIMARY
SMS_ID
100000124430
Created by admin on Thu Jul 06 06:49:38 UTC 2023 , Edited by admin on Thu Jul 06 06:49:38 UTC 2023
PRIMARY
CAS
1189805-46-6
Created by admin on Thu Jul 06 06:49:38 UTC 2023 , Edited by admin on Thu Jul 06 06:49:38 UTC 2023
PRIMARY
FDA UNII
8BA8T27317
Created by admin on Thu Jul 06 06:49:38 UTC 2023 , Edited by admin on Thu Jul 06 06:49:38 UTC 2023
PRIMARY
CHEBI
59331
Created by admin on Thu Jul 06 06:49:38 UTC 2023 , Edited by admin on Thu Jul 06 06:49:38 UTC 2023
PRIMARY
DRUG BANK
DB13108
Created by admin on Thu Jul 06 06:49:38 UTC 2023 , Edited by admin on Thu Jul 06 06:49:38 UTC 2023
PRIMARY
WIKIPEDIA
MEPHEDRONE
Created by admin on Thu Jul 06 06:49:38 UTC 2023 , Edited by admin on Thu Jul 06 06:49:38 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
SALT/SOLVATE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
In vitro studies suggest that mephedrone metabolic disposition is regulated by the highly polymorphic isoenzyme of CYP2D6 (Pedersen et al., 2013).
TARGET -> INHIBITOR
TARGET -> INHIBITOR
IC50
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