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
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
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
Title | Date | PubMed |
---|---|---|
UK places generic ban on mephedrone drug family. | 2010 Apr 17 |
|
A collapse in integrity of scientific advice in the UK. | 2010 Apr 17 |
|
A harmless high? | 2010 Aug 28 |
|
Headshop heartache: acute mephedrone 'meow' myocarditis. | 2010 Dec |
|
What should be done about mephedrone? | 2010 Mar 23 |
|
Home secretary bans mephedrone after taking advice from depleted council. | 2010 Mar 31 |
|
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 |
|
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 |
|
Neuronal changes and oxidative stress in adolescent rats after repeated exposure to mephedrone. | 2015 Jul 1 |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Jun 25 23:37:18 UTC 2021
by
admin
on
Fri Jun 25 23:37:18 UTC 2021
|
Record UNII |
8BA8T27317
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Code | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
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 | ||
---|---|---|---|---|---|
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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 | |||
|
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
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
METABOLITE -> PARENT |
IN-VIVO
URINE
|
||
|
METABOLITE -> PARENT |
IN VIVO
URINE
|
||
|
METABOLITE -> PARENT |
IN VIVO
URINE
|
||
|
METABOLITE -> PARENT |
IN VIVO
URINE
|
||
|
METABOLITE -> PARENT |
IN-VIVO
URINE
|
||
|
METABOLITE -> PARENT |
IN VIVO
URINE
|
||
|
METABOLITE -> PARENT |
IN VIVO
URINE
|
||
|
METABOLITE -> PARENT |
IN VIVO
URINE
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
IMPURITY -> PARENT |
IN VIVO
URINE
|
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |