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
Structure for Cathinone (DB01560)
- 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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of adverse effects can be increased when Cathinone is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of adverse effects can be increased when Acetazolamide is combined with Cathinone. Acetophenazine The risk or severity of adverse effects can be increased when Acetophenazine is combined with Cathinone. Aclidinium Cathinone may increase the central nervous system depressant (CNS depressant) activities of Aclidinium. Agomelatine The risk or severity of adverse effects can be increased when Cathinone is combined with Agomelatine. Alfentanil The risk or severity of adverse effects can be increased when Alfentanil is combined with Cathinone. Alimemazine The risk or severity of adverse effects can be increased when Alimemazine is combined with Cathinone. Almotriptan The risk or severity of adverse effects can be increased when Almotriptan is combined with Cathinone. Alosetron The risk or severity of adverse effects can be increased when Alosetron is combined with Cathinone. Alprazolam The risk or severity of adverse effects can be increased when Alprazolam is combined with Cathinone. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - 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
- Bentur Y, Bloom-Krasik A, Raikhlin-Eisenkraft B: Illicit cathinone ("Hagigat") poisoning. Clin Toxicol (Phila). 2008 Mar;46(3):206-10. [Article]
- External Links
- KEGG Compound
- C08301
- PubChem Compound
- 62258
- PubChem Substance
- 46508478
- ChemSpider
- 56062
- ChEBI
- 4110
- ChEMBL
- CHEMBL2104047
- ZINC
- ZINC000053165481
- Wikipedia
- Cathinone
Clinical Trials
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
Property Value Source Water Solubility 2.46 mg/mL ALOGPS logP 0.51 ALOGPS logP 1.18 ChemAxon logS -1.8 ALOGPS pKa (Strongest Acidic) 18.65 ChemAxon pKa (Strongest Basic) 7.55 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 43.09 Å2 ChemAxon Rotatable Bond Count 2 ChemAxon Refractivity 44.31 m3·mol-1 ChemAxon Polarizability 16.28 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - 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 inhibitor Non-inhibitor 0.9731 CYP450 2D6 inhibitor Non-inhibitor 0.8424 CYP450 2C19 inhibitor Non-inhibitor 0.8337 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Drug created at July 31, 2007 13:10 / Updated at February 21, 2021 18:51