You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameCathinone
Accession NumberDB01560
TypeSmall Molecule
GroupsIllicit
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
D-Cathinone
β-ketoamphetamine
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII540EI4406J
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[[email protected]](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
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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 inhibitorNon-inhibitor0.9731
CYP450 2D6 inhibitorNon-inhibitor0.8424
CYP450 2C19 inhibitorNon-inhibitor0.8337
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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 References
  1. Bentur Y, Bloom-Krasik A, Raikhlin-Eisenkraft B: Illicit cathinone ("Hagigat") poisoning. Clin Toxicol (Phila). 2008 Mar;46(3):206-10. [PubMed:17852166 ]
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcetazolamideAcetazolamide may decrease the excretion rate of Cathinone which could result in a lower serum level and potentially a reduction in efficacy.
Acetylsalicylic acidCathinone may increase the analgesic activities of Acetylsalicylic acid.
AlfentanilCathinone may increase the analgesic activities of Alfentanil.
Aluminum hydroxideAluminum hydroxide may decrease the excretion rate of Cathinone which could result in a lower serum level and potentially a reduction in efficacy.
AmitriptylineAmitriptyline may increase the stimulatory activities of Cathinone.
Ammonium chlorideThe serum concentration of Cathinone can be decreased when it is combined with Ammonium chloride.
AmoxapineAmoxapine may increase the stimulatory activities of Cathinone.
AripiprazoleAripiprazole may decrease the stimulatory activities of Cathinone.
AsenapineAsenapine may decrease the stimulatory activities of Cathinone.
AzelastineCathinone may decrease the sedative activities of Azelastine.
BrexpiprazoleBrexpiprazole may decrease the stimulatory activities of Cathinone.
BrompheniramineCathinone may decrease the sedative activities of Brompheniramine.
BuprenorphineCathinone may increase the analgesic activities of Buprenorphine.
ButorphanolCathinone may increase the analgesic activities of Butorphanol.
CaffeineCathinone may increase the analgesic activities of Caffeine.
Calcium carbonateCalcium carbonate may decrease the excretion rate of Cathinone which could result in a lower serum level and potentially a reduction in efficacy.
CarbinoxamineCathinone may decrease the sedative activities of Carbinoxamine.
CetirizineCathinone may decrease the sedative activities of Cetirizine.
ChlorphenamineCathinone may decrease the sedative activities of Chlorphenamine.
ChlorpromazineChlorpromazine may decrease the stimulatory activities of Cathinone.
ClemastineCathinone may decrease the sedative activities of Clemastine.
ClofedanolCathinone may decrease the sedative activities of Clofedanol.
ClomipramineClomipramine may increase the stimulatory activities of Cathinone.
ClozapineClozapine may decrease the stimulatory activities of Cathinone.
CodeineCathinone may increase the analgesic activities of Codeine.
CyclizineCathinone may decrease the sedative activities of Cyclizine.
CyproheptadineCathinone may decrease the sedative activities of Cyproheptadine.
DesipramineDesipramine may increase the stimulatory activities of Cathinone.
DesloratadineCathinone may decrease the sedative activities of Desloratadine.
DexbrompheniramineCathinone may decrease the sedative activities of Dexbrompheniramine.
Dexchlorpheniramine maleateCathinone may decrease the sedative activities of Dexchlorpheniramine maleate.
DiclofenamideDiclofenamide may decrease the excretion rate of Cathinone which could result in a lower serum level and potentially a reduction in efficacy.
DihydrocodeineCathinone may increase the analgesic activities of Dihydrocodeine.
DimenhydrinateCathinone may decrease the sedative activities of Dimenhydrinate.
DiphenhydramineCathinone may decrease the sedative activities of Diphenhydramine.
DoxepinDoxepin may increase the stimulatory activities of Cathinone.
DoxylamineCathinone may decrease the sedative activities of Doxylamine.
DroperidolDroperidol may decrease the stimulatory activities of Cathinone.
EthosuximideThe therapeutic efficacy of Ethosuximide can be decreased when used in combination with Cathinone.
FentanylCathinone may increase the analgesic activities of Fentanyl.
FexofenadineCathinone may decrease the sedative activities of Fexofenadine.
FlupentixolFlupentixol may decrease the stimulatory activities of Cathinone.
FluphenazineFluphenazine may decrease the stimulatory activities of Cathinone.
Fluticasone PropionateCathinone may decrease the sedative activities of Fluticasone Propionate.
HaloperidolHaloperidol may decrease the stimulatory activities of Cathinone.
HexamethylenetetramineThe serum concentration of Cathinone can be decreased when it is combined with Hexamethylenetetramine.
HydrocodoneCathinone may increase the analgesic activities of Hydrocodone.
HydromorphoneCathinone may increase the analgesic activities of Hydromorphone.
HydroxyzineCathinone may decrease the sedative activities of Hydroxyzine.
IloperidoneIloperidone may decrease the stimulatory activities of Cathinone.
ImipramineImipramine may increase the stimulatory activities of Cathinone.
Ioflupane I 123Cathinone may decrease effectiveness of Ioflupane I 123 as a diagnostic agent.
IsocarboxazidIsocarboxazid may increase the hypertensive activities of Cathinone.
Lactic AcidSodium lactate may decrease the excretion rate of Cathinone which could result in a lower serum level and potentially a reduction in efficacy.
LevocetirizineCathinone may decrease the sedative activities of Levocetirizine.
LevorphanolCathinone may increase the analgesic activities of Levorphanol.
LithiumLithium may decrease the stimulatory activities of Cathinone.
LoratadineCathinone may decrease the sedative activities of Loratadine.
LoxapineLoxapine may decrease the stimulatory activities of Cathinone.
LurasidoneLurasidone may decrease the stimulatory activities of Cathinone.
Magnesium hydroxideMagnesium hydroxide may decrease the excretion rate of Cathinone which could result in a lower serum level and potentially a reduction in efficacy.
MeclizineCathinone may decrease the sedative activities of Meclizine.
MethadoneCathinone may increase the analgesic activities of Methadone.
MethazolamideMethazolamide may decrease the excretion rate of Cathinone which could result in a lower serum level and potentially a reduction in efficacy.
MethotrimeprazineMethotrimeprazine may decrease the stimulatory activities of Cathinone.
MoclobemideMoclobemide may increase the hypertensive activities of Cathinone.
MorphineCathinone may increase the analgesic activities of Morphine.
NalbuphineCathinone may increase the analgesic activities of Nalbuphine.
NortriptylineNortriptyline may increase the stimulatory activities of Cathinone.
OlanzapineOlanzapine may decrease the stimulatory activities of Cathinone.
OlopatadineCathinone may decrease the sedative activities of Olopatadine.
OxycodoneCathinone may increase the analgesic activities of Oxycodone.
OxymorphoneCathinone may increase the analgesic activities of Oxymorphone.
PaliperidonePaliperidone may decrease the stimulatory activities of Cathinone.
PentazocineCathinone may increase the analgesic activities of Pentazocine.
PerphenazinePerphenazine may decrease the stimulatory activities of Cathinone.
PethidineCathinone may increase the analgesic activities of Pethidine.
PhenelzinePhenelzine may increase the hypertensive activities of Cathinone.
PhenobarbitalThe serum concentration of Phenobarbital can be decreased when it is combined with Cathinone.
PhenytoinThe serum concentration of Phenytoin can be decreased when it is combined with Cathinone.
PimozidePimozide may decrease the stimulatory activities of Cathinone.
PizotifenCathinone may decrease the sedative activities of Pizotifen.
ProcarbazineProcarbazine may increase the hypertensive activities of Cathinone.
ProchlorperazineProchlorperazine may decrease the stimulatory activities of Cathinone.
PromazinePromazine may decrease the stimulatory activities of Cathinone.
ProtriptylineProtriptyline may increase the stimulatory activities of Cathinone.
QuetiapineQuetiapine may decrease the stimulatory activities of Cathinone.
RasagilineRasagiline may increase the hypertensive activities of Cathinone.
RemifentanilCathinone may increase the analgesic activities of Remifentanil.
ReserpineThe serum concentration of Cathinone can be decreased when it is combined with Reserpine.
RisperidoneRisperidone may decrease the stimulatory activities of Cathinone.
SelegilineSelegiline may increase the hypertensive activities of Cathinone.
Sodium bicarbonateSodium bicarbonate may decrease the excretion rate of Cathinone which could result in a lower serum level and potentially a reduction in efficacy.
SufentanilCathinone may increase the analgesic activities of Sufentanil.
TapentadolCathinone may increase the analgesic activities of Tapentadol.
ThioridazineThioridazine may decrease the stimulatory activities of Cathinone.
ThiothixeneThiothixene may decrease the stimulatory activities of Cathinone.
TopiramateTopiramate may decrease the excretion rate of Cathinone which could result in a lower serum level and potentially a reduction in efficacy.
TramadolCathinone may increase the analgesic activities of Tramadol.
TranylcypromineTranylcypromine may increase the hypertensive activities of Cathinone.
TrifluoperazineTrifluoperazine may decrease the stimulatory activities of Cathinone.
TrimipramineTrimipramine may increase the stimulatory activities of Cathinone.
TriprolidineCathinone may decrease the sedative activities of Triprolidine.
Vitamin CThe serum concentration of Cathinone can be decreased when it is combined with Vitamin C.
ZiprasidoneZiprasidone may decrease the stimulatory activities of Cathinone.
ZonisamideZonisamide may decrease the excretion rate of Cathinone which could result in a lower serum level and potentially a reduction in efficacy.
ZuclopenthixolZuclopenthixol may decrease the stimulatory activities of Cathinone.
Food InteractionsNot Available
Comments
comments powered by Disqus
Drug created on July 31, 2007 07:10 / Updated on August 17, 2016 12:23