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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-13 11:48:23 UTC
Update Date2023-02-21 17:29:02 UTC
HMDB IDHMDB0041927
Secondary Accession Numbers
  • HMDB41927
Metabolite Identification
Common NameMethcathinone
DescriptionInjecting this substance has recently been associated with symptoms similar to those seen in patients with Parkinson's Disease (Manganism) due to the compound manganese dioxide which is a byproduct of synthesis with permanganate. Methcathinone (α-methylamino-propiophenone or ephedrone) is a psychoactive stimulant, sometimes used as a recreational drug and considered addictive. It is usually snorted, but can be smoked, injected, or taken orally. Methcathinone is currently a DEA Schedule I controlled substance in the United States. Methcathinone is a beta-keto N-methylampthetamine and is closely related to the naturally occurring compounds, cathinone and cathine. It is also very closely related to methamphetamine, differing by only the ketone substituent and differing from amphetamine by both a keto and N-methyl substituent. The C=O bond at the R-position (directly right of the benzene ring) is slightly polar, and as a result the drug does not cross the lipid blood-brain barrier quite as well as amphetamine. Nevertheless, it is a potent CNS stimulant and dopamine reuptake inhibitor. Chronic high dosage use may result in acute mental confusion ranging from mild paranoia to psychosis. These symptoms typically disappear quickly if use is stopped.
Structure
Thumb
Synonyms
ValueSource
2-(Methylamino)-1-phenyl-1-propanoneHMDB
2-(Methylamino)propiophenoneHMDB
2-Methylamino-1-phenylpropanoneHMDB
alpha-MethylaminopropiophenoneHMDB
CatHMDB
EphedroneHMDB
MonomethylpropionHMDB
Monomethylpropion hydrochloride, 14C-labeledHMDB
MethcathinoneMeSH
Chemical FormulaC10H13NO
Average Molecular Weight163.2163
Monoisotopic Molecular Weight163.099714043
IUPAC Name2-(methylamino)-1-phenylpropan-1-one
Traditional Namemethcathinone
CAS Registry Number5650-44-2
SMILES
CNC(C)C(=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C10H13NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,11H,1-2H3
InChI KeyLPLLVINFLBSFRP-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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Phenylpropane
  • Benzoyl
  • Aryl alkyl ketone
  • Benzenoid
  • Monocyclic benzene moiety
  • Alpha-aminoketone
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
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
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID1519
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethcathinone
METLIN IDNot Available
PubChem Compound1576
PDB IDNot Available
ChEBI ID149677
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available