Cathinone: Information from Answers.com



Cathinone
Systematic (IUPAC) name
(S)-2-amino-1-phenyl-1-propanone
Identifiers
CAS number	71031-15-7
ATC code	none
PubChem	62258
Chemical data
Formula	C₉H₁₁N O
Mol. mass	149.19 g/mol
Pharmacokinetic data
Bioavailability	?
Metabolism	?
Half life	?
Excretion	?
Therapeutic considerations
Pregnancy cat.	?
Legal status	Schedule III(CA) Class A(UK) Schedule I(US)
Routes	?

Cathinone (β-keto amphetamine) is a monoamine alkaloid found in the shrub Catha edulis (Khat) and is chemically similar to ephedrine, cathine and other amphetamines. Amphetamine induces the release of dopamine from striatal preparations that are prelabelled either with dopamine or its precursors, and it has been shown that cathinone also does this.^[1] It is probably the main contributor to the stimulant effect of Catha edulis. Cathinone differs from many other amphetamines in that it has a ketone functional group. Other amphetamines that 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.^[2] Circa 1993, the DEA added cathinone to the Controlled Substances Act's Schedule I in order to fulfill the requirements of international law.

The sale of khat is legal in Israel (although synthetic cathinone is not), and also in Oman, in Yemen, in United Kingdom and in the Horn of Africa.

Chemistry

The molecular structure of cathinone.

Cathinone is structurally related to methcathinone, much like how amphetamine is related to methamphetamine. Cathinone differs from amphetamine by possessing a ketone oxygen atom (C=O) on the β (beta) position of the side chain. The corresponding alcohol compound cathine is a less powerful stimulant. The biophysiological conversion from cathinone to cathine is to blame for the depotentiation of khat leaves over time. Fresh leaves have a greater ratio of cathinone to cathine than dried ones, therefore having more psychoactive effects.

Cathinone can be extracted from Catha edulis, or synthesized from α-bromo propiophenone (which is easily made from propiophenone).

References

^ Kalix, Peter (February 1981). "Cathinone, an alkaloid from khat leaves with an amphetamine-like releasing effect". Psychopharmacology 74 (3): 269–70. doi:10.1007/BF00427108. http://www.springerlink.com/content/n7v28h68627245j0/?p=95742099c2304cc9b83799274e8bbcdc&pi=2. Retrieved on 2008-02-11.
^ List of psychotropic substances under international control

This article needs additional citations for verification.
Please help improve this article by adding reliable references. Unsourced material may be challenged and removed. (December 2007)

External links

Erowid Cathinone Vault [1]
Cathinone Popularity Soars in Israel

v • d • e Amphetamines (N06BA)

Amphetamine/Dextroamphetamine · Dextromethamphetamine · Levomethamphetamine · 4-FA · 4-MTA · Benzphetamine · Ethylamphetamine · Propylamphetamine · MDMA · MDA · MDEA · Ephedrine · Parahydroxyamphetamine · Paramethoxyamphetamine · Paramethoxymethamphetamine · Paramethoxyethylamphetamine · Xylopropamine

v • d • e Stimulants

Adamantanes	Adaphenoxate • Adapromine • Bromantane • Chlodantane • Gludantane • Memantine • Midantane

Alkylamines	Cyclopentamine • Geranamine • Heptaminol • Isometheptene • Octodrine • Propylhexedrine • Tuaminoheptane (Tuamine)

Cholinergics	ABT-089 • ABT-418 • Anabasine • Arecoline • Cotinine • Cytisine • Dianicline • Epibatidine • Epiboxidine • GTS-21 • Ispronicline • Nicotine • Rivanicline • TC-5619 • Tebanicline • Varenicline

Convulsants	Bicuculline • DMCM • Flurothyl • Gabazine • Pentetrazol • Picrotoxin • Strychnine • Thujone

Eugeroics	Adrafinil • Armodafinil • Carphedon • Modafinil

Phenethylamines	1-Phenyl-2-methylaminobutan-1-one • 2-Phenyl-3-aminobutane • 2-Phenyl-3-methylaminobutane • 4-Bromomethcathinone • 4-FA • 4-Fluoromethamphetamine • 4-Fluoromethcathinone • 4-Ethylamphetamine • 4-Hydroxyephedrine (Oxilofrine) • 4-Methylamphetamine • 4-Methylmethamphetamine • Mephedrone (4-MMC) • 4-MTA • Alfetamine • Alpha-ethyl-phenethylamine • Amfepentorex • Amphechloral • Amphetamine (Dextroamphetamine, Adderall) • Amphetaminil • Benfluorex • Benzphetamine • β-Methylphenethylamine • Bupropion • Cathinone • Chlorphentermine • Clenbuterol • Clobenzorex • Clortermine • Diethylcathinone (Diethylpropion) • Dimethoxyamphetamine • Dimethylamphetamine • Dimethylcathinone • Ephedrine • Epinephrine • Ethcathinone • Ethylamphetamine • Fenbutrazate • Fencamine • Fenethylline • Fenfluramine • Fenproporex • Fludorex • Furfenorex • Levomethamphetamine • Lisdexamfetamine • MDMA (Ecstasy) • Mefenorex • Mephentermine • Methamphetamine • Methcathinone • Methoxyphedrine • Methoxyphenamine • Methylone • Norfenefrine • Octopamine • Ortetamine • Parahydroxyamphetamine • PCA • PIA • PMA • PMEA • PMMA • PPAP • Phendimetrazine • Phenmetrazine • Phenpentermine • Phenpromethamine • Phentermine • Phenylephrine • Phenylpropanolamine • Propylamphetamine • Pseudoephedrine • Selegiline • Synephrine • Tiflorex • Xylopropamine

Phenylaminooxazoles	4-Methylaminorex • Aminorex • Clominorex • Cyclazodone • Fenozolone • Fluminorex • Pemoline • Thozalinone

Piperazines	2C-B-BZP • BZP • DBL-583 • GBR-12783 • GBR-12935 • GBR-13069 • GBR-13098 • GBR-13119 • MeOPP • MBZP • Vanoxerine

Piperidines	2-Benzylpiperidine • 4-Benzylpiperidine • BTCP • Desoxypipradrol • Diphemethoxidine • Ethylphenidate • HDMP-28 • (-)-Methyl-1-methyl-4β-(2-naphthyl)piperidine-3β-carboxylate • Methylphenidate (Dexmethylphenidate) • Nocaine • Phacetoperane (Levofacetoperane) • Pipradrol (Meretran)

Pyrrolidinophenones	α-PPP • MDPPP • MDPV • MPBP • MPHP • MPPP • MOPPP • Pyrovalerone

Tropanes	3α-Bis-(4-fluorophenyl)methoxytropane • 3α-((4-Chlorophenyl)phenylmethoxy)tropane • 3-Pseudotropyl-4-fluorobenzoate • Altropane (IACFT) • Brasofensine • CFT (WIN 35,428) • β-CIT (RTI-55) • Cocaethylene • Cocaine • β-CPPIT • Dichloropane (RTI-111) • Difluoropine • FE-β-CPPIT • FP-β-CPPIT • Ioflupane (FPCIT) • Norcocaine • PIT • PTT • RTI-31 • RTI-32 • RTI-51 • RTI-112 • RTI-113 • RTI-121 (IPCIT) • RTI-126 • RTI-150 • RTI-171 • RTI-177 • RTI-336 • Tesofensine • Troparil (β-CPT, WIN 35,065-2) • Tropoxane • WF-23 • WF-33 • WF-60

Xanthines	Aminophylline • Caffeine • Dimethazan • Paraxanthine • Theobromine • Theophylline

Others	1-(Thiophen-2-yl)-2-aminopropane • 2-Aminoindane • 5-(2-Aminopropyl)indole • Amfonelic acid • Amineptine • Amiphenazole • Bemegride • Benzydamine • BPAP • BTQ • BTS 74,398 • Clofenciclan • Cropropamide • Crotetamide • Cypenamine • Cyprodenate • Diclofensine • Dimethocaine • Diphenylprolinol • Etamivan • Fencamfamine • Feprosidnine • Gilutensin • GYKI-52895 • Hexacyclonate • Indanorex • Indanylaminopropane • Indatraline • Lefetamine • Leptacline • LR-5182 • Manifaxine • Mazindol • Meclofexonate • Mefexamide • Mesocarb • Naphthylisopropylamine • Nikethamide • Nomifensine • O-2172 • Phthalimidopropiophenone • Prolintane • Sibutramine • Tametraline • UH-232 • Yohimbine • Zylofuramine

See also Sympathomimetic amines

Dopaminergics

Receptor Ligands

Agonists	Benzazepine-derivatives: Fenoldopam • SKF 38393 • SKF 82958; Ergot-derivatives: Bromocriptine • Cabergoline • Dihydroergocryptine • Lisuride • Pergolide; Dihydrexidine-derivatives: A-86929 • Dihydrexidine • Dinapsoline • Dinoxyline • Doxathrine; Morphine-derivatives: Apomorphine • Propylnorapomorphine; Piperazine-derivatives: Aripiprazole • Piribedil • WAY-100,635; Others: A-412,997 • Aplindore • Memantine • Pramipexole • Pukateine • Quinpirole • Ropinirole • Rotigotine

Antagonists	Typical Antipsychotics: Acepromazine • Azaperone • Benperidol • Bromperidol • Clopenthixol • Chlorpromazine • Chlorprothixene • Droperidol • Flupentixol • Fluphenazine • Fluspirilene • Haloperidol • Loxapine • Mesoridazine • Methotrimeprazine • Molindone • Penfluridol • Perazine • Periciazine • Perphenazine • Pimozide • Prochlorperazine • Promazine • Sulforidazine • Thioridazine • Thiothixene • Trifluoperazine • Triflupromazine • Trifluperidol • Zuclopenthixol; Atypical Antipsychotics: Amisulpride • Asenapine • Clozapine • Iloperidone • Melperone • Olanzapine • Paliperidone • Perospirone • Quetiapine • Risperidone • Sertindole • Sulpiride • Ziprasidone • Zotepine; Antiemetics: Alizapride • Bromopride • Clebopride • Domperidone • Metoclopramide • Thiethylperazine; Others: Amoxapine • Blonanserin • Buspirone • Butaclamol • Eticlopride • Fananserin • Mosapramine • Nafadotride • Nemonapride • Nuciferine • Raclopride • Remoxipride • SB-277,011-A • SCH 23390 • Spiperone • Spiroxatrine • Stepholidine • Tetrahydropalmatine • Tiapride • UH-232 • Yohimbine

Reuptake Inhibitors

Plasmalemmal

DAT Inhibitors	Piperazine-derivatives: DBL-583 • GBR-12935 • Nefazodone • Vanoxerine; Piperidine-derivatives: BTCP • Desoxypipradrol • Dextromethylphenidate • Ethylphenidate • HDMP-28 • Methylphenidate • Phencyclidine • Pipradrol; Pyrovalerone-derivatives: MDPV • Pyrovalerone; Tropane-derivatives: β-CPPIT • Altropane • Brasofensine • CFT • Cocaine • Dichloropane • Difluoropine • FE-β-CPPIT • FP-β-CPPIT • Ioflupane • Lometopane • RTI-121 • RTI-126 • RTI-150 • RTI-336 • Tenocyclidine • Tesofensine • Troparil • Tropoxane • WF-11 • WF-23 • WF-31 • WF-33; Others: Amfonelic Acid • Amineptine • Benztropine • Bromantane • BTQ • BTS 74,398 • Bupropion • Cypenamine • Diclofensine • Dimethocaine • Diphenylprolinol • Dizocilpine • DOV 102,677 • DOV 21,947 • DOV 216,303 • Ethcathinone • Fencamfamine • GYKI-52895 • Indatraline • Ketamine • Lefetamine • LR-5182 • Manifaxine • Mazindol • Medifoxamine • Mesocarb • Nisoxetine • Nomifensine • NS2359 • O-2172 • Prolintane • Radafaxine • SEP-225289 • SEP-227162 • Sibutramine • Tametraline

TRPC6 Activators	Adhyperforin • Hyperforin

Vesicular

VMAT Inhibitors

Ibogaine • Reserpine • Tetrabenazine

Releasing Agents

Alkylamine-derivatives: Cyclopentamine • Propylhexedrine; Aminopropane-derivatives: Indanylaminopropane • Naphthylaminopropane; Oxazoline-derivatives: 4-Methylaminorex • Aminorex • Pemoline; Phenethylamine-derivatives: 4-Fluoroamphetamine • 4-Fluoromethamphetamine • Amphetamine • Amphetaminil • Amfepentorex • Benzphetamine • Butylone • Cathine • Cathinone • Clobenzorex • Dextroamphetamine • Diethylcathinone • Dimethylamphetamine • Dimethylcathinone • Ethylamphetamine • Ethylone • Fenethylline • Fenproporex • Flephedrone • Furfenorex • Lisdexamfetamine • MBDB • MDA • MDEA • MDMA • Mefenorex • Mephedrone • Methamphetamine • Methcathinone • Methylone • Phendimetrazine • Phenethylamine • Phenmetrazine • PMA • PMEA • PMMA • Propylamphetamine • Tyramine • Xylopropamine; Piperazine-derivatives: BZP • MBZP • MeOPP; Others: 4-Benzylpiperidine • Zylofuramine

Enzyme Inhibitors

Anabolism

PAH Inhibitors	3,4-Dihydroxystyrene

TH Inhibitors	3-Iodotyrosine • Aquayamycin • Bulbocapnine • Metirosine • Oudenone

AAAD Inhibitors	Benserazide • Carbidopa

Catabolism

MAO Inhibitors	Nonselective: Iproclozide • Iproniazid • Isocarboxazid • Nialamide • Phenelzine • Pheniprazine • Tranylcypromine; MAO-A Selective: Befloxatone • Brofaromine • Cimoxatone • Clorgiline • Harmala Alkaloids • Minaprine • Moclobemide • Pirlindole • Toloxatone • Tyrima; MAO-B Selective: Lazabemide • Pargyline • Rasagiline • Selegiline

COMT Inhibitors	Entacapone • Tolcapone

DBH Inhibitors	Disulfiram • Nepicastat • Tropolone

Others

Precursors	L-Phenylalanine • L-Tyrosine • L-DOPA

Cofactors	Iron • Tetrahydrobiopterin • Vitamin B3 (Niacin/Nicotinamide/NADPH) • Vitamin B6 (Pyridoxine/Pyridoxamine/Pyridoxal 5-Phosphate) • Vitamin B9 (Folic Acid/Tetrahydrofolic Acid) • Vitamin C (Ascorbic Acid) • Zinc

Others	Activity Enhancers: BPAP • PPAP; Others: Amantadine • Memantine • Rimantadine

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	What is the uses of cathinone?
	What is the pka of cathinone?

	khat
	staff tree (tree, plant)
	Stimulants