U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C11H13NO3
Molecular Weight 207.2258
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MDMC

SMILES

CNC(C)C(=O)C1=CC=C2OCOC2=C1

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 207.2258
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

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

Unknown
139594
PubMed

PubMed

TitleDatePubMed
The disposition into hair of new designer drugs; methylone, MBDB and methcathinone.
2007 Aug 15
[Analysis of designer drugs detected in the products purchased in fiscal year 2006].
2008 Oct
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
Substance Class Chemical
Created
by admin
on Sat Dec 16 00:25:43 GMT 2023
Edited
by admin
on Sat Dec 16 00:25:43 GMT 2023
Record UNII
L4I4B1R01F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MDMC
Common Name English
1-PROPANONE, 1-(1,3-BENZODIOXOL-5-YL)-2-(METHYLAMINO)-
Systematic Name English
.BETA.K-MDMA
Common Name English
2-METHYLAMINO-1-(3,4-METHYLENEDIOXYPHENYL)PROPAN-1-ONE
Systematic Name English
M1 (PSYCHEDELIC)
Common Name English
METHYLENEDIOXYMETHCATHINONE
Common Name English
METHYLONE
Common Name English
J899.632F
Code English
3,4-METHYLENEDIOXY-N-METHYLCATHINONE
Systematic Name English
Classification Tree Code System Code
DEA NO. 7540
Created by admin on Sat Dec 16 00:25:43 GMT 2023 , Edited by admin on Sat Dec 16 00:25:43 GMT 2023
WIKIPEDIA Designer-drugs-Methylone
Created by admin on Sat Dec 16 00:25:43 GMT 2023 , Edited by admin on Sat Dec 16 00:25:43 GMT 2023
WIKIPEDIA PiHKAL
Created by admin on Sat Dec 16 00:25:43 GMT 2023 , Edited by admin on Sat Dec 16 00:25:43 GMT 2023
Code System Code Type Description
CAS
186028-79-5
Created by admin on Sat Dec 16 00:25:43 GMT 2023 , Edited by admin on Sat Dec 16 00:25:43 GMT 2023
PRIMARY
EVMPD
SUB90507
Created by admin on Sat Dec 16 00:25:43 GMT 2023 , Edited by admin on Sat Dec 16 00:25:43 GMT 2023
PRIMARY
PUBCHEM
45789647
Created by admin on Sat Dec 16 00:25:43 GMT 2023 , Edited by admin on Sat Dec 16 00:25:43 GMT 2023
PRIMARY
WIKIPEDIA
METHYLONE
Created by admin on Sat Dec 16 00:25:43 GMT 2023 , Edited by admin on Sat Dec 16 00:25:43 GMT 2023
PRIMARY
SMS_ID
100000140993
Created by admin on Sat Dec 16 00:25:43 GMT 2023 , Edited by admin on Sat Dec 16 00:25:43 GMT 2023
PRIMARY
MESH
C400939
Created by admin on Sat Dec 16 00:25:43 GMT 2023 , Edited by admin on Sat Dec 16 00:25:43 GMT 2023
PRIMARY
EPA CompTox
DTXSID80870167
Created by admin on Sat Dec 16 00:25:43 GMT 2023 , Edited by admin on Sat Dec 16 00:25:43 GMT 2023
PRIMARY
HSDB
7997
Created by admin on Sat Dec 16 00:25:43 GMT 2023 , Edited by admin on Sat Dec 16 00:25:43 GMT 2023
PRIMARY
FDA UNII
L4I4B1R01F
Created by admin on Sat Dec 16 00:25:43 GMT 2023 , Edited by admin on Sat Dec 16 00:25:43 GMT 2023
PRIMARY
Related Record Type Details
SODIUM-DEPENDENT DOPAMINE TRANSPORTER
TARGET -> INHIBITOR
CYTOCHROME P450 2B6
METABOLIC ENZYME -> SUBSTRATE
CYTOCHROME P450 1A2
METABOLIC ENZYME -> SUBSTRATE
MINOR
CYTOCHROME P450 2C19
METABOLIC ENZYME -> SUBSTRATE
MINOR
CYTOCHROME P450 2D6
METABOLIC ENZYME -> SUBSTRATE
MAJOR
Structure of MDMC, (S)-
ENANTIOMER -> RACEMATE
SODIUM-DEPENDENT NORADRENALINE TRANSPORTER
TARGET -> INHIBITOR
SODIUM-DEPENDENT SEROTONIN TRANSPORTER
TARGET -> INHIBITOR
Structure of MDMC hydrochloride
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of 3-HYDROXY-4-METHOXYMETHCATHINONE
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
Structure of BK-MDA
METABOLITE -> PARENT
IN-VITRO
Scientific Literature
Structure of BK-MDA
METABOLITE -> PARENT
IN-VIVO
URINE
Structure of DIHYDROXYMETHCATHINONE
METABOLITE -> PARENT
IN VITRO
MAJOR
Structure of 4-HMMC
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
Structure of DIHYDRO-METHYLONE
METABOLITE -> PARENT
IN VITRO
Structure of 1-(1,3-BENZODIOXOL-5-YL)-2-(HYDROXYMETHYLAMINO)-1-PROPANONE
METABOLITE -> PARENT
IN VITRO
Related Record Type Details
Structure of MDMC
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966