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
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
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
Title | Date | PubMed |
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Analyses of second-generation 'legal highs' in the UK: initial findings. | 2010 Aug |
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A harmless high? | 2010 Aug 28 |
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Mephedrone is an amphetamine "by another name," drug adviser tells MPs. | 2010 Mar 24 |
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Home secretary bans mephedrone after taking advice from depleted council. | 2010 Mar 31 |
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Dependence and psychosis with 4-methylmethcathinone (mephedrone) use. | 2010 Nov 3 |
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Methaemoglobinaemia due to mephedrone ('snow'). | 2010 Oct 22 |
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Recreational use of mephedrone (4-methylmethcathinone, 4-MMC) with associated sympathomimetic toxicity. | 2010 Sep |
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The serotonin syndrome as a result of mephedrone toxicity. | 2010 Sep 20 |
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Mephedrone: use, subjective effects and health risks. | 2011 Nov |
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Instability of the ecstasy market and a new kid on the block: mephedrone. | 2011 Nov |
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Neuronal changes and oxidative stress in adolescent rats after repeated exposure to mephedrone. | 2015 Jul 1 |
Patents
Substance Class |
Chemical
Created
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admin
on
Edited
Sat Dec 16 00:23:35 GMT 2023
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Sat Dec 16 00:23:35 GMT 2023
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Record UNII |
8BA8T27317
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Validated (UNII)
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1248
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WIKIPEDIA |
Designer-drugs-4-Methylmethcathinone
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MEPHEDRONE
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In vitro studies suggest that mephedrone metabolic disposition is regulated by the highly polymorphic isoenzyme of CYP2D6 (Pedersen et al., 2013).
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