NAV

Cathinone

Identification

Generic Name
Cathinone
DrugBank Accession Number
DB01560
Background

Cathinone 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 categorized as a Schedule I drug. Cathinone was added to the Controlled Substances Act's Schedule I in 1993 in compliance with international laws.

Type
Small Molecule
Groups
Illicit
Structure
3D
Similar Structures
Weight
Average: 149.1897
Monoisotopic: 149.084063979
Chemical Formula
C9H11NO
Synonyms
  • alpha-Aminopropiophenone
  • Cathinone
  • Cathinonum
  • Catinona
  • D-Cathinone
  • Norephedrone
External IDs
  • C08301
  • J18.754B

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
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1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when Cathinone is combined with 1,2-Benzodiazepine.
AcetazolamideThe risk or severity of adverse effects can be increased when Acetazolamide is combined with Cathinone.
AcetophenazineThe risk or severity of adverse effects can be increased when Acetophenazine is combined with Cathinone.
AclidiniumCathinone may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
AgomelatineThe risk or severity of adverse effects can be increased when Cathinone is combined with Agomelatine.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Cathinone.
AlimemazineThe risk or severity of adverse effects can be increased when Alimemazine is combined with Cathinone.
AlmotriptanThe risk or severity of adverse effects can be increased when Almotriptan is combined with Cathinone.
AlosetronThe risk or severity of adverse effects can be increased when Alosetron is combined with Cathinone.
AlprazolamThe risk or severity of adverse effects can be increased when Alprazolam is combined with Cathinone.
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
Kingdom
Organic compounds
Super Class
Organic oxygen compounds
Class
Organooxygen compounds
Sub Class
Carbonyl 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 / Alpha-aminoketone / Amine / Aromatic homomonocyclic compound / Aryl alkyl ketone / Benzenoid / Benzoyl / Hydrocarbon derivative / Monocyclic benzene moiety / Organic nitrogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
2-aminopropiophenone, monoamine alkaloid (CHEBI:4110) / Phenylalanine derived alkaloids (C08301)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
540EI4406J
CAS number
71031-15-7
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[C@H](N)C(=O)C1=CC=CC=C1

References

General References
  1. Bentur Y, Bloom-Krasik A, Raikhlin-Eisenkraft B: Illicit cathinone ("Hagigat") poisoning. Clin Toxicol (Phila). 2008 Mar;46(3):206-10. [Article]
KEGG Compound
C08301
PubChem Compound
62258
PubChem Substance
46508478
ChemSpider
56062
ChEBI
4110
ChEMBL
CHEMBL2104047
ZINC
ZINC000053165481
Wikipedia
Cathinone

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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)18.89ChemAxon
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

Drug created at July 31, 2007 13:10 / Updated at February 21, 2021 18:51