Cathinone

Identification

Name
Cathinone
Accession Number
DB01560
Type
Small Molecule
Groups
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
  • D-Cathinone
  • β-ketoamphetamine
External IDs
C08301 / J18.754B
Categories
UNII
540EI4406J
CAS number
71031-15-7
Weight
Average: 149.1897
Monoisotopic: 149.084063979
Chemical Formula
C9H11NO
InChI Key
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

Synthesis Reference
Not 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
KEGG Compound
C08301
PubChem Compound
62258
PubChem Substance
46508478
ChemSpider
56062
ChEBI
4110
ChEMBL
CHEMBL2104047
Wikipedia
Cathinone
ATC Codes
Not Available
AHFS Codes
Not Available
PDB Entries
Not Available
FDA label
Not Available
MSDS
Not Available

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not 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 FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
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 )

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of chemical entities known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
Kingdom
Chemical entities
Super Class
Organic compounds
Class
Organic oxygen compounds
Sub Class
Organooxygen compounds
Direct Parent
Alkyl-phenylketones
Alternative Parents
Phenylpropanes / Benzoyl derivatives / Aryl alkyl ketones / Alpha-amino ketones / Organopnictogen compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives
Substituents
Alkyl-phenylketone / Phenylpropane / Benzoyl / Aryl alkyl ketone / Benzenoid / Monocyclic benzene moiety / Alpha-aminoketone / Hydrocarbon derivative / Amine / Primary amine
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
2-aminopropiophenone, monoamine alkaloid (CHEBI:4110 ) / Phenylalanine derived alkaloids (C08301 )

Drug created on July 31, 2007 07:10 / Updated on October 02, 2017 05:00