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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:48:10 UTC
Update Date2017-12-07 04:29:31 UTC
HMDB IDHMDB0041923
Secondary Accession Numbers
  • HMDB41923
Metabolite Identification
Common NameMephedrone
DescriptionIn 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
Thumb
Synonyms
ValueSource
4-MethylephedroneChEBI
4-MethylmethcathinoneChEBI
4-MMCChEBI
MMCAT compoundMeSH
beta-keto-4-MethylmethamphetamineMeSH
BK-4-MethylmethamphetamineMeSH
4-MMC CompoundMeSH
Chemical FormulaC11H15NO
Average Molecular Weight177.2429
Monoisotopic Molecular Weight177.115364107
IUPAC Name2-(methylamino)-1-(4-methylphenyl)propan-1-one
Traditional Namemephedrone
CAS Registry Number1189805-46-6
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 KeyYELGFTGWJGBAQU-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location:

Role

Industrial application:

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.72 g/LALOGPS
logP1.33ALOGPS
logP2.12ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)18.66ChemAxon
pKa (Strongest Basic)8.05ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.1 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity54.13 m³·mol⁻¹ChemAxon
Polarizability20.66 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0aor-9600000000-99e304f4c8722d5f7b2fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-01ot-0900000000-63a56a651f789a893e55View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0900000000-72c24c862242c481aca4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-c5357ff91e06cdd98e2fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0900000000-a293b8fd331ba92afc2bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0900000000-ab08f3ff9c43c678a409View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-01ot-0900000000-0e8d2be244e2c2b90065View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-c36f9c805707cdca4596View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0005-0900000000-0a4988d65ddec4e44b3dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-004i-0900000000-03bb00bf907535516e3dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0900000000-692e09986df677e5ecc1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0900000000-33cea69ee5f543869c02View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-01ot-0900000000-888d4a226b1d533a2ea2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0002-0900000000-5717c7c0504ffa0c6054View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-0005-0900000000-f4e14927b85bb7d9e5b4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-03di-0900000000-3fd3aa739f1f8f082f8dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0900000000-c2af763936f70e0e62b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-2900000000-4dbb835577330ade2938View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aou-9400000000-a67ebd5163dd4b071d47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-0900000000-67c1c193c4560d0eb743View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-2900000000-8ada81709ad2898e4982View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-8900000000-da4b7522d2d2139fc9b2View in MoNA
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID21485694
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMephedrone
METLIN IDNot Available
PubChem Compound45266826
PDB IDNot Available
ChEBI ID59331
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available