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Details

Stereochemistry RACEMIC
Molecular Formula C11H15NO
Molecular Weight 177.2433
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEPHEDRONE

SMILES

Cc1ccc(cc1)C(=O)C(C)NC

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 177.2433
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
UK places generic ban on mephedrone drug family.
2010 Apr 17
Khat use and monitoring drug use in Europe: the current situation and issues for the future.
2010 Dec 1
[Mephedrone: A designer drug legally available on the Web].
2010 Jul-Aug
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
Britain moves to curtail new drug craze.
2010 Jun 15
What should be done about mephedrone?
2010 Mar 23
Home secretary bans mephedrone after taking advice from depleted council.
2010 Mar 31
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
A case of extreme agitation and death after the use of mephedrone in The Netherlands.
2011 Mar 20
Patents
Substance Class Chemical
Created
by admin
on Fri Jun 25 23:37:18 UTC 2021
Edited
by admin
on Fri Jun 25 23:37:18 UTC 2021
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 Fri Jun 25 23:37:18 UTC 2021 , Edited by admin on Fri Jun 25 23:37:18 UTC 2021
Code System Code Type Description
PUBCHEM
45266826
Created by admin on Fri Jun 25 23:37:18 UTC 2021 , Edited by admin on Fri Jun 25 23:37:18 UTC 2021
PRIMARY
HSDB
7979
Created by admin on Fri Jun 25 23:37:18 UTC 2021 , Edited by admin on Fri Jun 25 23:37:18 UTC 2021
PRIMARY
EVMPD
SUB32114
Created by admin on Fri Jun 25 23:37:18 UTC 2021 , Edited by admin on Fri Jun 25 23:37:18 UTC 2021
PRIMARY
MESH
C548233
Created by admin on Fri Jun 25 23:37:18 UTC 2021 , Edited by admin on Fri Jun 25 23:37:18 UTC 2021
PRIMARY
CAS
1189805-46-6
Created by admin on Fri Jun 25 23:37:18 UTC 2021 , Edited by admin on Fri Jun 25 23:37:18 UTC 2021
PRIMARY
FDA UNII
8BA8T27317
Created by admin on Fri Jun 25 23:37:18 UTC 2021 , Edited by admin on Fri Jun 25 23:37:18 UTC 2021
PRIMARY
DRUG BANK
DB13108
Created by admin on Fri Jun 25 23:37:18 UTC 2021 , Edited by admin on Fri Jun 25 23:37:18 UTC 2021
PRIMARY
WIKIPEDIA
MEPHEDRONE
Created by admin on Fri Jun 25 23:37:18 UTC 2021 , Edited by admin on Fri Jun 25 23:37:18 UTC 2021
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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