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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
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
Categories
CAS number71031-15-7
WeightAverage: 149.1897
Monoisotopic: 149.084063979
Chemical FormulaC9H11NO
InChI KeyInChIKey=PUAQLLVFLMYYJJ-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenethylamines
Direct parentAmphetamines and Derivatives
Alternative parentsAcetophenones; Benzoyl Derivatives; Ketones; Enolates; Polyamines; Monoalkylamines
Substituentsbenzoyl; ketone; enolate; polyamine; amine; primary amine; primary aliphatic amine; carbonyl group; organonitrogen compound
Classification descriptionThis compound belongs to the amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
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
Property Value Probability
Human Intestinal Absorption + 1.0
Blood Brain Barrier + 0.9382
Caco-2 permeable + 0.8723
P-glycoprotein substrate Non-substrate 0.8
P-glycoprotein inhibitor I Non-inhibitor 0.964
P-glycoprotein inhibitor II Non-inhibitor 0.9809
Renal organic cation transporter Non-inhibitor 0.865
CYP450 2C9 substrate Non-substrate 0.8029
CYP450 2D6 substrate Non-substrate 0.9115
CYP450 3A4 substrate Non-substrate 0.786
CYP450 1A2 substrate Non-inhibitor 0.7534
CYP450 2C9 substrate Non-inhibitor 0.9731
CYP450 2D6 substrate Non-inhibitor 0.8424
CYP450 2C19 substrate Non-inhibitor 0.8337
CYP450 3A4 substrate Non-inhibitor 0.9273
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8611
Ames test Non AMES toxic 0.9105
Carcinogenicity Non-carcinogens 0.707
Biodegradation Ready biodegradable 0.5786
Rat acute toxicity 2.2186 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9486
hERG inhibition (predictor II) Non-inhibitor 0.9655
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
water solubility2.46e+00 g/lALOGPS
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 area43.09ChemAxon
rotatable bond count2ChemAxon
refractivity44.31ChemAxon
polarizability16.28ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
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
ResourceLink
KEGG CompoundC08301
PubChem Compound62258
PubChem Substance46508478
ChemSpider56062
WikipediaCathinone
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
Drug created on July 31, 2007 07:10 / Updated on September 16, 2013 17:15