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Details

Stereochemistry RACEMIC
Molecular Formula C11H13NO3
Molecular Weight 207.2262
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYLONE

SMILES

CC(C(=O)c1ccc2c(c1)OCO2)NC

InChI

InChIKey=VKEQBMCRQDSRET-UHFFFAOYSA-N
InChI=1S/C11H13NO3/c1-7(12-2)11(13)8-3-4-9-10(5-8)15-6-14-9/h3-5,7,12H,6H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C11H13NO3
Molecular Weight 207.2262
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Methylone (3, 4-Methylenedioxy-N-methylcathinone), a β-keto analog of 3,4-methylenedioxy-N-methylamphetamine (MDMA) is a stimulant and psychoactive drug. Methylone is a popular drug of abuse that strongly increases the release of the three monoamines: dopamine, serotonin (5-HT) and norepinephrine. In addition, methylone inhibits plasma membrane catecholamine transporters but only weakly inhibit the vesicle transporter. In April 2013, methylone was listed in the Schedule 1 substance under the Controlled Substances Act.

Approval Year

PubMed

PubMed

TitleDatePubMed
Methylone and mCPP, two new drugs of abuse?
2005 Dec
Metabolism of the recently encountered designer drug, methylone, in humans and rats.
2006 Aug
The disposition into hair of new designer drugs; methylone, MBDB and methcathinone.
2007 Aug 15
Combined intoxication with methylone and 5-MeO-MIPT.
2007 Jan 30
The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain.
2007 Mar 22
[Analysis of designer drugs detected in the products purchased in fiscal year 2006].
2008 Oct
Cytotoxic effects of 3,4-methylenedioxy-N-alkylamphetamines, MDMA and its analogues, on isolated rat hepatocytes.
2009 Jan
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
Head shop compound abuse amongst attendees of the Drug Treatment Centre Board.
2010 May
Modulation of human GABAA receptor function: a novel mode of action of drugs of abuse.
2011 Dec
Substance Class Chemical
Created
by admin
on Sat Jun 26 01:37:11 UTC 2021
Edited
by admin
on Sat Jun 26 01:37:11 UTC 2021
Record UNII
L4I4B1R01F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHYLONE
Common Name English
1-PROPANONE, 1-(1,3-BENZODIOXOL-5-YL)-2-(METHYLAMINO)-
Systematic Name English
2-METHYLAMINO-1-(3,4-METHYLENEDIOXYPHENYL)PROPAN-1-ONE
Systematic Name English
METHYLENEDIOXYMETHCATHINONE
Common Name English
BK-MDMA
Common Name English
M1
Common Name English
J899.632F
Code English
3,4-METHYLENEDIOXY-N-METHYLCATHINONE
Common Name English
Classification Tree Code System Code
DEA NO. 7540
Created by admin on Sat Jun 26 01:37:11 UTC 2021 , Edited by admin on Sat Jun 26 01:37:11 UTC 2021
Code System Code Type Description
CAS
186028-79-5
Created by admin on Sat Jun 26 01:37:11 UTC 2021 , Edited by admin on Sat Jun 26 01:37:11 UTC 2021
PRIMARY
EVMPD
SUB90507
Created by admin on Sat Jun 26 01:37:11 UTC 2021 , Edited by admin on Sat Jun 26 01:37:11 UTC 2021
PRIMARY
PUBCHEM
45789647
Created by admin on Sat Jun 26 01:37:11 UTC 2021 , Edited by admin on Sat Jun 26 01:37:11 UTC 2021
PRIMARY
WIKIPEDIA
METHYLONE
Created by admin on Sat Jun 26 01:37:11 UTC 2021 , Edited by admin on Sat Jun 26 01:37:11 UTC 2021
PRIMARY
MESH
C400939
Created by admin on Sat Jun 26 01:37:11 UTC 2021 , Edited by admin on Sat Jun 26 01:37:11 UTC 2021
PRIMARY
HSDB
7997
Created by admin on Sat Jun 26 01:37:11 UTC 2021 , Edited by admin on Sat Jun 26 01:37:11 UTC 2021
PRIMARY
FDA UNII
L4I4B1R01F
Created by admin on Sat Jun 26 01:37:11 UTC 2021 , Edited by admin on Sat Jun 26 01:37:11 UTC 2021
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
MINOR
METABOLIC ENZYME -> SUBSTRATE
MINOR
METABOLIC ENZYME -> SUBSTRATE
MAJOR
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE -> PARENT
No free form was detected. After hydrolysis, 74 ng/mL of 3-HMMC was observed in a methylone abuser's urine specimen.
IN-VIVO
URINE
METABOLITE -> PARENT
IN-VITRO
Scientific Literature
METABOLITE -> PARENT
IN-VIVO
URINE
METABOLITE -> PARENT
IN VITRO
MAJOR
METABOLITE -> PARENT
No free form was detected. After hydrolysis, 170 ng/mL of $-HMMC was observed in a methylone abuser's urine specimen.
IN-VIVO
URINE
METABOLITE -> PARENT
IN VITRO
METABOLITE -> PARENT
IN VITRO
Related Record Type Details
ACTIVE MOIETY