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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-13 11:48:10 UTC

Update Date

2023-02-21 17:29:02 UTC

HMDB ID

HMDB0041923

Secondary Accession Numbers

HMDB41923

Metabolite Identification

Common Name

Mephedrone

Description

In 2010, unconfirmed reports speculated about the role mephedrone has played in the deaths of several young people in the UK. By July 2010, mephedrone had been alleged to be involved in 52 fatalities in the UK, but detected in only 38 of these cases. Of the nine that coroners had finished investigating, two were caused directly by mephedrone. The first death reported to be caused by mephedrone use was that of 46-year-old, John Sterling Smith, who had underlying health problems and repeatedly injected the drug. A report in Forensic Science International in August 2010 stated mephedrone intoxication has been recorded as the cause of death in two cases in Scotland. Post mortem samples showed the concentration of mephedrone in their blood was 22 mg/l in one case and 3.3 mg/l in the other. The death of a teenager in the UK in November 2009 was widely reported as being caused by mephedrone, but a report by the coroner concluded she had died from natural causes. In March 2010, the deaths of two teenagers in Scunthorpe were widely reported by the media to be caused by mephedrone. Toxicology reports showed the teenagers had not taken any mephedrone and had died as a result of consuming alcohol and the heroin substitute methadone. According to Fiona Measham, a criminologist who is a member of the ACMD, the reporting of the unconfirmed deaths by newspapers followed 'the usual cycle of exaggeration, distortion, inaccuracy and sensationalism'' associated with the reporting of recreational drug use. Mephedrone is a white substance. It is sold most commonly as crystals or a powder, but also in the form of capsules or pills. It can have a distinctive odour, reported to range from a synthetic fishy smell to the smell of vanilla and bleach, stale urine, or electric circuit boards. Mephedrone is one of hundreds of designer drugs or legal highs that have been reported in recent years, including artificial chemicals such as synthetic cannabis and semisynthetic substances such as methylhexaneamine. These drugs are primarily developed to avoid being controlled by laws against illegal drugs, thus giving them the label of designer drugs. According to the European Monitoring Centre for Drugs and Drug Addiction, the synthesis of mephedrone was first reported in 1929 by Saem de Burnaga Sanchez in the Bulletin de la Societe Chimique de France, under the name 'toluyl-alpha-monomethylaminoethylcetone',:17 but the compound remained an obscure product of academia until 2003, when it was 're-discovered' and publicised by an underground chemist on The Hive website, working under the pseudonym 'Kinetic'. Mephedrone, also known as 4-methylmethcathinone (4-MMC), or 4-methylephedrone, is a synthetic stimulant drug of the amphetamine and cathinone classes. Slang names include meph, drone, MCAT, meow meow, and bubble. It is reportedly manufactured in China and is chemically similar to the cathinone compounds found in the khat plant of eastern Africa. It comes in the form of tablets or a powder, which users can swallow, snort or inject, producing similar effects to MDMA, amphetamines, and cocaine.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 13-SEP-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-12         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       0.000   6.160   0.000  0.00  0.00           N+0
HETATM   13  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   12                                                            
CONECT    4    6    8                                                       
CONECT    5    7    8                                                       
CONECT    6    4   10                                                       
CONECT    7    5   10                                                       
CONECT    8    1    4    5                                                  
CONECT    9    2   11   12                                                  
CONECT   10    6    7   11                                                  
CONECT   11    9   10   13                                                  
CONECT   12    3    9                                                       
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0041923
HETATM    1  C1  UNL     1      -4.245   0.440   0.719  1.00  0.00           C  
HETATM    2  N1  UNL     1      -3.252  -0.611   0.838  1.00  0.00           N  
HETATM    3  C2  UNL     1      -1.942  -0.009   0.531  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.030   0.463  -0.907  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.856  -0.966   0.730  1.00  0.00           C  
HETATM    6  O1  UNL     1      -1.118  -2.131   1.113  1.00  0.00           O  
HETATM    7  C5  UNL     1       0.533  -0.607   0.496  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.556  -1.534   0.691  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.885  -1.231   0.481  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.245   0.030   0.061  1.00  0.00           C  
HETATM   11  C9  UNL     1       4.657   0.424  -0.184  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.240   0.951  -0.134  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.906   0.660   0.073  1.00  0.00           C  
HETATM   14  H1  UNL     1      -5.084   0.094   0.049  1.00  0.00           H  
HETATM   15  H2  UNL     1      -3.828   1.335   0.184  1.00  0.00           H  
HETATM   16  H3  UNL     1      -4.623   0.790   1.697  1.00  0.00           H  
HETATM   17  H4  UNL     1      -3.442  -1.386   0.162  1.00  0.00           H  
HETATM   18  H5  UNL     1      -1.885   0.883   1.197  1.00  0.00           H  
HETATM   19  H6  UNL     1      -1.219   0.091  -1.545  1.00  0.00           H  
HETATM   20  H7  UNL     1      -2.983   0.139  -1.407  1.00  0.00           H  
HETATM   21  H8  UNL     1      -2.068   1.589  -0.969  1.00  0.00           H  
HETATM   22  H9  UNL     1       1.295  -2.529   1.021  1.00  0.00           H  
HETATM   23  H10 UNL     1       3.636  -1.989   0.648  1.00  0.00           H  
HETATM   24  H11 UNL     1       4.780   0.805  -1.239  1.00  0.00           H  
HETATM   25  H12 UNL     1       4.863   1.311   0.460  1.00  0.00           H  
HETATM   26  H13 UNL     1       5.346  -0.408   0.023  1.00  0.00           H  
HETATM   27  H14 UNL     1       2.472   1.970  -0.468  1.00  0.00           H  
HETATM   28  H15 UNL     1       0.158   1.429  -0.097  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3   17
CONECT    3    4    5   18
CONECT    4   19   20   21
CONECT    5    6    6    7
CONECT    7    8    8   13
CONECT    8    9   22
CONECT    9   10   10   23
CONECT   10   11   12
CONECT   11   24   25   26
CONECT   12   13   13   27
CONECT   13   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4-Methylephedrone	ChEBI
4-Methylmethcathinone	ChEBI
4-MMC	ChEBI
MMCAT compound	HMDB
beta-Keto-4-methylmethamphetamine	HMDB
BK-4-Methylmethamphetamine	HMDB
4-MMC Compound	HMDB

Chemical Formula

C₁₁H₁₅NO

Average Molecular Weight

177.2429

Monoisotopic Molecular Weight

177.115364107

IUPAC Name

2-(methylamino)-1-(4-methylphenyl)propan-1-one

Traditional Name

mephedrone

CAS Registry Number

1189805-46-6

SMILES

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

InChI Identifier

InChI=1S/C11H15NO/c1-8-4-6-10(7-5-8)11(13)9(2)12-3/h4-7,9,12H,1-3H3

InChI Key

YELGFTGWJGBAQU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-phenylketones

Alternative Parents

Substituents

Alkyl-phenylketone
Phenylpropane
Benzoyl
Aryl alkyl ketone
Toluene
Monocyclic benzene moiety
Benzenoid
Alpha-aminoketone
Secondary aliphatic amine
Secondary amine
Organonitrogen compound
Organic nitrogen compound
Organic oxide
Organopnictogen compound
Hydrocarbon derivative
Amine
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

amphetamines (CHEBI:59331 )
propanone (CHEBI:59331 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0041923)

Source

Exogenous

Exogenous (HMDB: HMDB0041923)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	143.1	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.72 g/L	ALOGPS
logP	1.33	ALOGPS
logP	2.12	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	18.66	ChemAxon
pKa (Strongest Basic)	8.05	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.1 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	54.13 m³·mol⁻¹	ChemAxon
Polarizability	20.66 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	142.7	31661259
DarkChem	[M-H]-	140.117	31661259
DeepCCS	[M+H]+	143.493	30932474
DeepCCS	[M-H]-	140.714	30932474
DeepCCS	[M-2H]-	176.652	30932474
DeepCCS	[M+Na]+	152.191	30932474
AllCCS	[M+H]+	139.5	32859911
AllCCS	[M+H-H2O]+	135.2	32859911
AllCCS	[M+NH4]+	143.5	32859911
AllCCS	[M+Na]+	144.7	32859911
AllCCS	[M-H]-	142.9	32859911
AllCCS	[M+Na-2H]-	143.9	32859911
AllCCS	[M+HCOO]-	145.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.99 minutes	32390414
Predicted by Siyang on May 30, 2022	10.636 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.01 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	41.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1260.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	296.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	131.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	179.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	85.0 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	303.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	363.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	122.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	895.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	357.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1003.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	220.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	284.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	348.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	220.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	64.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Mephedrone	CNC(C)C(=O)C1=CC=C(C)C=C1	1934.5	Standard polar	33892256
Mephedrone	CNC(C)C(=O)C1=CC=C(C)C=C1	1432.0	Standard non polar	33892256
Mephedrone	CNC(C)C(=O)C1=CC=C(C)C=C1	1472.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Mephedrone,1TMS,isomer #1	CC1=CC=C(C(=O)C(C)N(C)[Si](C)(C)C)C=C1	1600.1	Semi standard non polar	33892256
Mephedrone,1TMS,isomer #1	CC1=CC=C(C(=O)C(C)N(C)[Si](C)(C)C)C=C1	1676.1	Standard non polar	33892256
Mephedrone,1TBDMS,isomer #1	CC1=CC=C(C(=O)C(C)N(C)[Si](C)(C)C(C)(C)C)C=C1	1859.9	Semi standard non polar	33892256
Mephedrone,1TBDMS,isomer #1	CC1=CC=C(C(=O)C(C)N(C)[Si](C)(C)C(C)(C)C)C=C1	1878.3	Standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB13108

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

21485694

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Mephedrone

METLIN ID

Not Available

PubChem Compound

45266826

PDB ID

Not Available

ChEBI ID

59331

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Mephedrone (HMDB0041923)

MOL for HMDB0041923 (Mephedrone)

3D MOL for HMDB0041923 (Mephedrone)

3D SDF for HMDB0041923 (Mephedrone)

3D-SDF for HMDB0041923 (Mephedrone)

PDB for HMDB0041923 (Mephedrone)

3D PDB for HMDB0041923 (Mephedrone)

SMILES for HMDB0041923 (Mephedrone)

INCHI for HMDB0041923 (Mephedrone)

Structure for HMDB0041923 (Mephedrone)

3D Structure for HMDB0041923 (Mephedrone)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized