Cathinone
(2S)-2-amino-1-phenylpropan-1-one
Overview
Cathinone belongs to Stimulants / Cathinones.
Effects
Subjective effects vary. What a substance feels like depends on dose, individual physiology,
mindset, and setting. The points below describe commonly reported effects, not guaranteed, uniform, or
desirable outcomes.
- Stimulant euphoria, increased alertness, talkativeness and sociability: the sought-after effects of khat chewing.
- Appetite suppression and sympathomimetic effects: raised heart rate and blood pressure, dry mouth and insomnia.
- A 'come-down' of low mood, irritability, lethargy and craving. Heavy or prolonged use can provoke anxiety or psychosis.
Dosing & duration
Harm-reduction note: These are commonly cited reference ranges, not a recommendation or a
“safe” dose. Potency, purity, body chemistry, tolerance, and drug combinations vary widely. Start
low, go slow, wait for full effects before redosing, and never assume an unknown product matches these
figures. Missing data is not evidence of safety.
Not reported
Dose ranges
Duration
Chemical & Physical Properties
| Formula | C9H11NO |
| Molar mass | 149.19 g/mol |
| State | Not reported |
| Melting point | 46.5 °C |
| Boiling point | 93 °C at 0.8 mmHg |
| Density | Not reported |
| Vapor pressure | Not reported |
| pKa | Not reported |
| LogP | 1.1 (predicted, XLogP3) |
| Solubility | Very soluble in ether, ethanol |
| Refractive index | Not reported |
Identifiers & Synonyms
| CAS | 71031-15-7 |
| CAS (enantiomer) | |
| PubChem CID | 62258 |
| InChIKey | 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 |
| SMILES | C[C@@H](C(=O)C1=CC=CC=C1)N |
Synonyms
- Cathinone
- (S)-(−)-Cathinone
- β-ketoamphetamine
- Benzoylethanamine
Pharmacodynamics & Biochemistry
Cathinone is the principal psychoactive alkaloid of khat (Catha edulis), the shrub whose fresh leaves are chewed as a stimulant across East Africa and the Arabian Peninsula. Chemically it is the β-keto analogue of amphetamine, often called a 'natural amphetamine', and the natural, more active form is (S)-(−)-cathinone. Like amphetamine, cathinone is a substrate-type releasing agent at the monoamine transporters: it is taken up into neurons and triggers release of noradrenaline and dopamine (a norepinephrine–dopamine releasing agent, NDRA), with only weak serotonin release. Reported release potencies are highest at NET and DAT (EC50 in the tens of nanomolar) and far weaker at SERT (micromolar): a DA-over-serotonin profile typical of reinforcing, high-abuse-liability stimulants. Cathinone is somewhat less potent than amphetamine. Its β-keto group makes the molecule more polar (lower logP), so it penetrates the CNS less readily. Combined with the slow oral route of khat chewing, this gives a gentler, less intense effect than injected or insufflated amphetamines. It is metabolised chiefly by reduction of the ketone to cathine (norpseudoephedrine) and norephedrine, both weaker stimulants. Because cathinone breaks down as the leaves dry, fresh khat is markedly more potent than aged material, which contains mostly cathine.
Biological targets
- DAT
- NET
Binding & functional measurements
| Target | Measurement | Species |
|---|---|---|
| Noradrenaline transporter | EC50 26 nM | Rat |
| Dopamine transporter | EC50 35 nM | Rat |
| Serotonin transporter | EC50 7,595 nM | Rat |
| Dopamine transporter | EC50 5,640 nM | Human |
| Noradrenaline transporter | Ki 3,500 ± 2,700 nM | Human |
| TAAR1 | Ki 2,100 ± 730 nM | Mouse |
| TAAR1 | Ki 2,200 ± 700 nM | Rat |
| α1A-adrenoceptor | Ki 5,400 ± 1,100 nM | Human |
| α2-adrenoceptor | Ki 8,900 ± 2,700 nM | Human |
Pharmacokinetics
| Bioavailability | Absorbed through the oral mucosa and gut during khat chewing, onset over ~15–60 min, peaking ~1.5–3.5 h |
| Tmax | Not reported |
| Half-life | Short (≈1.5–3 h) |
| Vd | Not reported |
| Protein binding | Not reported |
| Metabolism | Hepatic reduction to cathine (norpseudoephedrine) and norephedrine |
| Excretion | Not reported |
Toxicology & Safety
Harm-reduction note: Toxicity and risk depend on dose, route, purity, combinations, setting, and individual
health factors. Missing harms should never be interpreted as evidence of safety.
Not reported
Cathinone is a sympathomimetic stimulant. Acute effects include raised heart rate and blood pressure, and khat use is linked to cardiovascular strain (hypertension, arrhythmia and an increased risk of myocardial infarction) as well as psychiatric effects (anxiety, insomnia and, with heavy use, psychosis). Chronic khat chewing is associated with dental and oral disease (including oral cancer), gastrointestinal problems and psychological dependence with a withdrawal syndrome (lethargy, low mood, craving). Risks rise when khat is combined with other stimulants, alcohol or tobacco.[4][2]
Legal Status
Legal note: Legal status can change over time and may vary by country, region, formulation, analogue status,
prescription context, and enforcement practice. Always confirm with current official sources before relying on this section.
US: Schedule I. UK: Class C. DE: BtMG Anlage I
Interactions & Contraindications
Drug interactions
Stimulants (amphetamines, cocaine) Additive cardiovascular and CNS stimulation with other sympathomimetics, raising the risk of hypertension, arrhythmia and anxiety or psychosis.[4]
Other serotonergic drugs, MAOIs Can compound sympathomimetic effects and blood-pressure spikes, caution with antidepressants.[2]
Alcohol, Caffeine Khat is commonly taken with tobacco, alcohol and caffeine, compounding cardiovascular load.[4]
Contraindications
Cardiovascular disease, hypertension or arrhythmia hypertension, ischaemic heart disease or arrhythmia.[4]
Personal or family history of psychosis, schizophrenia or bipolar disorder psychotic disorders or severe anxiety.[4]
Pregnancy or breastfeeding khat use is associated with low birth weight.[2]
Concurrent MAOI, SSRI/SNRI or other serotonergic medication concurrent MAO inhibitors, or other stimulants.[4]
No interactions or contraindications listed.
Usage & Context
- The active principle of khat (Catha edulis), whose fresh leaves are chewed as a traditional social stimulant in East Africa and the Arabian Peninsula.
- Not used therapeutically. Controlled internationally as a drug of abuse. Structurally it is the parent of the large 'synthetic cathinone' family (mephedrone, methylone, MDPV and others).
- Because cathinone degrades to cathine as leaves dry, khat is traded and consumed fresh: a fact that shapes its distribution and potency.
Sources & Evidence
- PubChem: Cathinone (CID 62258) — identifiers & computed properties
- Wikipedia: Cathinone (khat alkaloid — pharmacology, metabolism & legal status) CC BY-SA 4.0
- Kalix P (1992). Cathinone, a natural amphetamine. Pharmacol Toxicol 70:77-86.
PMID 1508843 · doi:10.1111/j.1600-0773.1992.tb00434.x
- Feyissa AM, Kelly JP (2008). A review of the neuropharmacological properties of khat. Prog Neuropsychopharmacol Biol Psychiatry 32:1147-66.
PMID 18561890 · doi:10.1016/j.pnpbp.2007.12.033
- Blough BE, Decker AM, Landavazo A, et al. (2019). The dopamine, serotonin and norepinephrine releasing activities of a series of methcathinone analogs in male rat brain synaptosomes. Psychopharmacology (Berl) 236:915-924.
PMID 30341459 · doi:10.1007/s00213-018-5063-9
- Fitzgerald LR, Gannon BM, Walther D, et al. (2024). Structure-activity relationships for locomotor stimulant effects and monoamine transporter interactions of substituted amphetamines and cathinones. Neuropharmacology 245:109827.
PMID 38154512 · doi:10.1016/j.neuropharm.2023.109827
- Simmler LD, Buser TA, Donzelli M, et al. (2013). Pharmacological characterization of designer cathinones in vitro. Br J Pharmacol 168:458-70.
PMID 22897747 · doi:10.1111/j.1476-5381.2012.02145.x