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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
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 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 Interactions
Drug
AcetazolamideCarbonic Anhydrase Inhibitors may decrease the excretion of Amphetamines.
AlfentanilMay enhance the analgesic effect of Analgesics (Opioid).
Aluminum hydroxideAntacids may decrease the excretion of Amphetamines.
AmitriptylineTricyclic Antidepressants may enhance the stimulatory effect of Amphetamines. Tricyclic Antidepressants may also potentiate the cardiovascular effects of Amphetamines.
Ammonium chlorideAmmonium Chloride may decrease the serum concentration of Amphetamines. This effect is likely due to an enhanced excretion of amphetamines in the urine.
AmoxapineTricyclic Antidepressants may enhance the stimulatory effect of Amphetamines. Tricyclic Antidepressants may also potentiate the cardiovascular effects of Amphetamines.
AripiprazoleAntipsychotic Agents may diminish the stimulatory effect of Amphetamines.
AsenapineAntipsychotic Agents may diminish the stimulatory effect of Amphetamines.
AzelastineMay diminish the sedative effect of Antihistamines.
BrompheniramineMay diminish the sedative effect of Antihistamines.
BuprenorphineMay enhance the analgesic effect of Analgesics (Opioid).
ButorphanolMay enhance the analgesic effect of Analgesics (Opioid).
Calcium carbonateAntacids may decrease the excretion of Amphetamines.
CarbinoxamineMay diminish the sedative effect of Antihistamines.
CetirizineMay diminish the sedative effect of Antihistamines.
ChlorphenamineMay diminish the sedative effect of Antihistamines.
ChlorpromazineAntipsychotic Agents may diminish the stimulatory effect of Amphetamines.
ClemastineMay diminish the sedative effect of Antihistamines.
ClomipramineTricyclic Antidepressants may enhance the stimulatory effect of Amphetamines. Tricyclic Antidepressants may also potentiate the cardiovascular effects of Amphetamines.
ClozapineAntipsychotic Agents may diminish the stimulatory effect of Amphetamines.
CodeineMay enhance the analgesic effect of Analgesics (Opioid).
CyclizineMay diminish the sedative effect of Antihistamines.
CyproheptadineMay diminish the sedative effect of Antihistamines.
DesipramineTricyclic Antidepressants may enhance the stimulatory effect of Amphetamines. Tricyclic Antidepressants may also potentiate the cardiovascular effects of Amphetamines.
DesloratadineMay diminish the sedative effect of Antihistamines.
DexbrompheniramineMay diminish the sedative effect of Antihistamines.
DihydrocodeineMay enhance the analgesic effect of Analgesics (Opioid).
DimenhydrinateMay diminish the sedative effect of Antihistamines.
DoxylamineMay diminish the sedative effect of Antihistamines.
DroperidolAntipsychotic Agents may diminish the stimulatory effect of Amphetamines.
EthosuximideMay diminish the therapeutic effect of Ethosuximide. Amphetamines may decrease the serum concentration of Ethosuximide.
FentanylMay enhance the analgesic effect of Analgesics (Opioid).
FexofenadineMay diminish the sedative effect of Antihistamines.
FlupentixolAntipsychotic Agents may diminish the stimulatory effect of Amphetamines.
Fluticasone PropionateMay diminish the sedative effect of Antihistamines.
HaloperidolAntipsychotic Agents may diminish the stimulatory effect of Amphetamines.
HydrocodoneMay enhance the analgesic effect of Analgesics (Opioid).
HydromorphoneMay enhance the analgesic effect of Analgesics (Opioid).
HydroxyzineMay diminish the sedative effect of Antihistamines.
IloperidoneAntipsychotic Agents may diminish the stimulatory effect of Amphetamines.
ImipramineTricyclic Antidepressants may enhance the stimulatory effect of Amphetamines. Tricyclic Antidepressants may also potentiate the cardiovascular effects of Amphetamines.
Ioflupane I 123May diminish the diagnostic effect of Ioflupane I 123.
IsocarboxazidMAO Inhibitors may enhance the hypertensive effect of Amphetamines. While linezolid and tedizolid may interact via this mechanism, management recommendations differ from other monoamine oxidase inhibitors. Refer to monographs specific to those agents for details.
KetotifenMay diminish the sedative effect of Antihistamines.
LevocetirizineMay diminish the sedative effect of Antihistamines.
LevorphanolMay enhance the analgesic effect of Analgesics (Opioid).
LithiumLithium may diminish the stimulatory effect of Amphetamines.
LoratadineMay diminish the sedative effect of Antihistamines.
LoxapineAntipsychotic Agents may diminish the stimulatory effect of Amphetamines.
LurasidoneAntipsychotic Agents may diminish the stimulatory effect of Amphetamines.
MeclizineMay diminish the sedative effect of Antihistamines.
MethadoneMay enhance the analgesic effect of Analgesics (Opioid).
MethazolamideCarbonic Anhydrase Inhibitors may decrease the excretion of Amphetamines.
Methenamine hippurateMethenamine may decrease the serum concentration of Amphetamines. This effect is likely due to an enhanced excretion of amphetamines in the urine.
Methenamine mandelateMethenamine may decrease the serum concentration of Amphetamines. This effect is likely due to an enhanced excretion of amphetamines in the urine.
MethotrimeprazineAntipsychotic Agents may diminish the stimulatory effect of Amphetamines.
MoclobemideMAO Inhibitors may enhance the hypertensive effect of Amphetamines. While linezolid and tedizolid may interact via this mechanism, management recommendations differ from other monoamine oxidase inhibitors. Refer to monographs specific to those agents for details.
MorphineMay enhance the analgesic effect of Analgesics (Opioid).
NalbuphineMay enhance the analgesic effect of Analgesics (Opioid).
NortriptylineTricyclic Antidepressants may enhance the stimulatory effect of Amphetamines. Tricyclic Antidepressants may also potentiate the cardiovascular effects of Amphetamines.
OlanzapineAntipsychotic Agents may diminish the stimulatory effect of Amphetamines.
OlopatadineMay diminish the sedative effect of Antihistamines.
OxycodoneMay enhance the analgesic effect of Analgesics (Opioid).
OxymorphoneMay enhance the analgesic effect of Analgesics (Opioid).
PaliperidoneAntipsychotic Agents may diminish the stimulatory effect of Amphetamines.
PerphenazineAntipsychotic Agents may diminish the stimulatory effect of Amphetamines.
PethidineMay enhance the analgesic effect of Analgesics (Opioid).
PhenelzineMAO Inhibitors may enhance the hypertensive effect of Amphetamines. While linezolid and tedizolid may interact via this mechanism, management recommendations differ from other monoamine oxidase inhibitors. Refer to monographs specific to those agents for details.
PhenobarbitalMay decrease the serum concentration of PHENobarbital.
PhenytoinMay decrease the serum concentration of Phenytoin.
PimozideAntipsychotic Agents may diminish the stimulatory effect of Amphetamines.
PizotifenMay diminish the sedative effect of Antihistamines.
ProcarbazineMAO Inhibitors may enhance the hypertensive effect of Amphetamines. While linezolid and tedizolid may interact via this mechanism, management recommendations differ from other monoamine oxidase inhibitors. Refer to monographs specific to those agents for details.
ProchlorperazineAntipsychotic Agents may diminish the stimulatory effect of Amphetamines.
PromazineAntipsychotic Agents may diminish the stimulatory effect of Amphetamines.
ProtriptylineTricyclic Antidepressants may enhance the stimulatory effect of Amphetamines. Tricyclic Antidepressants may also potentiate the cardiovascular effects of Amphetamines.
QuetiapineAntipsychotic Agents may diminish the stimulatory effect of Amphetamines.
RasagilineMAO Inhibitors may enhance the hypertensive effect of Amphetamines. While linezolid and tedizolid may interact via this mechanism, management recommendations differ from other monoamine oxidase inhibitors. Refer to monographs specific to those agents for details.
RemifentanilMay enhance the analgesic effect of Analgesics (Opioid).
ReserpineGastrointestinal Acidifying Agents may decrease the serum concentration of Amphetamines.
RisperidoneAntipsychotic Agents may diminish the stimulatory effect of Amphetamines.
SelegilineMAO Inhibitors may enhance the hypertensive effect of Amphetamines. While linezolid and tedizolid may interact via this mechanism, management recommendations differ from other monoamine oxidase inhibitors. Refer to monographs specific to those agents for details.
Sodium bicarbonateAlkalinizing Agents may decrease the excretion of Amphetamines.
SufentanilMay enhance the analgesic effect of Analgesics (Opioid).
TapentadolMay enhance the analgesic effect of Analgesics (Opioid).
ThioridazineAntipsychotic Agents may diminish the stimulatory effect of Amphetamines.
ThiothixeneAntipsychotic Agents may diminish the stimulatory effect of Amphetamines.
TopiramateCarbonic Anhydrase Inhibitors may decrease the excretion of Amphetamines.
TramadolMay enhance the analgesic effect of Analgesics (Opioid).
TranylcypromineMAO Inhibitors may enhance the hypertensive effect of Amphetamines. While linezolid and tedizolid may interact via this mechanism, management recommendations differ from other monoamine oxidase inhibitors. Refer to monographs specific to those agents for details.
TrifluoperazineAntipsychotic Agents may diminish the stimulatory effect of Amphetamines.
TrimipramineTricyclic Antidepressants may enhance the stimulatory effect of Amphetamines. Tricyclic Antidepressants may also potentiate the cardiovascular effects of Amphetamines.
TriprolidineMay diminish the sedative effect of Antihistamines.
ZiprasidoneAntipsychotic Agents may diminish the stimulatory effect of Amphetamines.
ZonisamideCarbonic Anhydrase Inhibitors may decrease the excretion of Amphetamines.
ZuclopenthixolAntipsychotic Agents may diminish the stimulatory effect of Amphetamines.
Food InteractionsNot Available
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Drug created on July 31, 2007 07:10 / Updated on September 16, 2013 17:15