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Identification
NameCathinone
Accession NumberDB01560
TypeSmall Molecule
GroupsExperimental, Illicit
Description

Cathinone (β-ketoamphetamine) is a monoamine alkaloid found in the shrub Catha edulis (Khat). Closely related to ephedrine, cathine and other amphetamines, it is probably the main contributor to the stimulant effect of Catha edulis. Cathinone differs from many other amphetamines in that its structure is a ketone. Other amphetamines to share this structure include the antidepressant bupropion and the stimulant methcathinone, among others. Internationally, cathinone is a Schedule I drug under the Convention on Psychotropic Substances. Circa 1993, the DEA added cathinone to the Controlled Substances Act’s Schedule I in order to fulfill the requirements of international law. [Wikipedia]

Structure
Thumb
Synonyms
SynonymLanguageCode
D-CathinoneNot AvailableNot Available
β-ketoamphetamineNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number71031-15-7
WeightAverage: 149.1897
Monoisotopic: 149.084063979
Chemical FormulaC9H11NO
InChI KeyPUAQLLVFLMYYJJ-ZETCQYMHSA-N
InChI
InChI=1S/C9H11NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7H,10H2,1H3/t7-/m0/s1
IUPAC Name
(2S)-2-amino-1-phenylpropan-1-one
SMILES
C[C@H](N)C(=O)C1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as acetophenones. These are organic compounds containing the acetophenone structure.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassAcetophenones
Direct ParentAcetophenones
Alternative Parents
Substituents
  • Phenylpropane
  • Acetophenone
  • Aryl alkyl ketone
  • Aryl ketone
  • Benzoyl
  • Alpha-aminoketone
  • Ketone
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9382
Caco-2 permeable+0.8723
P-glycoprotein substrateNon-substrate0.8
P-glycoprotein inhibitor INon-inhibitor0.964
P-glycoprotein inhibitor IINon-inhibitor0.9809
Renal organic cation transporterNon-inhibitor0.865
CYP450 2C9 substrateNon-substrate0.8029
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateNon-substrate0.786
CYP450 1A2 substrateNon-inhibitor0.7534
CYP450 2C9 substrateNon-inhibitor0.9731
CYP450 2D6 substrateNon-inhibitor0.8424
CYP450 2C19 substrateNon-inhibitor0.8337
CYP450 3A4 substrateNon-inhibitor0.9273
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8611
Ames testNon AMES toxic0.9105
CarcinogenicityNon-carcinogens0.707
BiodegradationReady biodegradable0.5786
Rat acute toxicity2.2186 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9486
hERG inhibition (predictor II)Non-inhibitor0.9655
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.46 mg/mLALOGPS
logP0.51ALOGPS
logP1.18ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)18.65ChemAxon
pKa (Strongest Basic)7.55ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area43.09 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.31 m3·mol-1ChemAxon
Polarizability16.28 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. Bentur Y, Bloom-Krasik A, Raikhlin-Eisenkraft B: Illicit cathinone (“Hagigat”) poisoning. Clin Toxicol (Phila). 2007 Aug 15;:1-5. Pubmed
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
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Drug created on July 31, 2007 07:10 / Updated on September 16, 2013 17:15