Cathinone

CAS# 71031-15-7

Cathinone

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Chemical structure

Cathinone

3D structure

Chemical Properties of Cathinone

Cas No. 71031-15-7 SDF Download SDF
PubChem ID 62258 Appearance Cryst.
Formula C9H11NO M.Wt 149.19
Type of Compound Alkaloids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (2S)-2-amino-1-phenylpropan-1-one
SMILES CC(C(=O)C1=CC=CC=C1)N
Standard InChIKey PUAQLLVFLMYYJJ-ZETCQYMHSA-N
Standard InChI InChI=1S/C9H11NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7H,10H2,1H3/t7-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Cathinone

The herbs of Catha edulis

Biological Activity of Cathinone

Description1. Cathinone is the main psychoactive constituent of the khat leaf and this alkaloid is a natural amphetamine, cathinone shares the action of amphetamine on CNS as well as its sympathomimetic effects. 2. (-)-Cathinone has reproductive toxicity in rats. 3. Cathinone generates oxidative stress hampered antioxidant enzymes, glutathione and lipid peroxidation. 4. Cathinone induces significant behavioral changes and CNS activation in the hamster by systemic administration. 5. Cathinone causes hormonal alterations probably via changes in hypothalamo-hypophyseo-adrenocortical and gonadal axes integrity. 6. Cathinone has amphetamine-like effects, it can produce increases in blood pressure and in heart rate, and these changes are concomitant with the presence of cathinone in blood plasma, it has in humans euphorigenic and psychostimulant effects. 7. Cathinone has vasoconstrictor activity which is not due to indirect or direct sympathomimetic activity, the coronary vasoconstriction may explain the increased incidence of myocardial infarction in khat chewers, which may arise from coronary vasospasm.
TargetsNMDAR

Cathinone Dilution Calculator

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Preparing Stock Solutions of Cathinone

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 6.7029 mL 33.5143 mL 67.0286 mL 134.0572 mL 167.5716 mL
5 mM 1.3406 mL 6.7029 mL 13.4057 mL 26.8114 mL 33.5143 mL
10 mM 0.6703 mL 3.3514 mL 6.7029 mL 13.4057 mL 16.7572 mL
50 mM 0.1341 mL 0.6703 mL 1.3406 mL 2.6811 mL 3.3514 mL
100 mM 0.067 mL 0.3351 mL 0.6703 mL 1.3406 mL 1.6757 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Cathinone

Amphetamine-like effects in humans of the khat alkaloid cathinone.[Pubmed:2288828]

Br J Clin Pharmacol. 1990 Dec;30(6):825-8.

1. The chewing of khat leaves as a stimulant is common in certain countries, and the effects of this material are supposed to be due to the phenylalkylamine alkaloid Cathinone. In order to determine the effects of this substance in humans, a single oral dose of Cathinone or placebo was administered to six healthy male volunteers in a double-blind, random order crossover study. 2. Cathinone produced increases in blood pressure and in heart rate, and these changes were concomitant with the presence of Cathinone in blood plasma. 3. The physical and mental changes that the subjects reported during the experiment indicated that Cathinone has in humans euphorigenic and psychostimulant effects. 4. These observations support the assumption that Cathinone is the constituent mainly responsible for the effects of khat, and they show that this alkaloid has also in humans amphetamine-like effects.

Cathinone, an active principle of Catha edulis, accelerates oxidative stress in the limbic area of swiss albino mice.[Pubmed:25153022]

J Ethnopharmacol. 2014 Oct 28;156:102-6.

ETHNOPHARMACOLOGICAL RELEVANCE: Cathinone hydrochloride is an active principle of the khat plant (Catha edulis) that produces pleasurable and stimulating effects in khat chewers. To the best of our knowledge no data of Cathinone on oxidative stress in limbic areas of mice is available. This is the first study of Cathinone on oxidative stress in limbic areas of the brain in Swiss albino male mice. MATERIALS AND METHODS: The animals were divided into four groups. Group-I was the control group and received vehicle, while groups-II to IV received (-)-Cathinone hydrochloride (0.125, 0.25 and 0.5 mg/kg body wt., i.p.) once daily for 15 days. RESULTS: The level of lipid peroxidation (LPO) was elevated dose-dependently and was significant (p<0.05, p<0.01) with doses of 0.25 and 0.5mg/kg body wt. of Cathinone as compared to control group. In contrast, the content of reduced glutathione (GSH) was decreased significantly (p<0.01, p<0.001) with doses of 0.25 and 0.5mg/kg body wt. of Cathinone as compared to control group. The activity of antioxidant enzymes (GPx, GR, GST, CAT, and SOD) was also decreased dose-dependently: the decreased activity of GPx, GR, catalase and SOD was significant with doses of 0.25 and 0.5 mg of Cathinone as compared to control group, while the activity of GST was decreased dose-dependently and was significant with 0.5mg of Cathinone as compared to control group. CONCLUSIONS: The results indicate that the Cathinone generated oxidative stress hampered antioxidant enzymes, glutathione and lipid peroxidation.

An evaluation of the male reproductive toxicity of cathinone.[Pubmed:2315943]

Toxicology. 1990 Mar 16;60(3):223-34.

(-)-Cathinone is the major psychoactive component of khat plant (Catha edulis Forssk.). Khat has been shown to produce reproductive toxicity in human beings and experimental animals. However, the chemical constituents of khat leaves responsible for sexual dysfunction are not known. In the present study Cathinone enantiomers have been investigated for their reproductive toxicity in rats. Cathinone produced a dose-dependent decrease in food consumption and suppressed the gain in body weight. There was a significant decrease in sperm count and motility and increase in the number of abnormal sperms in Cathinone treated animals. Histopathological examination of testes revealed degeneration of interstitial tissue, cellular infiltration and atrophy of Sertoli and Leydig's cells in Cathinone treated animals. Cathinone also produced a significant decrease in plasma testosterone levels of the rats. Although both enantiomers of Cathinone produced deleterious effects on male reproductive system, (-)-Cathinone was found to be more toxic. From this study it may be concluded that the Cathinone content in khat may be partially or totally responsible for the reproductive toxicity in khat chewers.

Cathinone, a natural amphetamine.[Pubmed:1508843]

Pharmacol Toxicol. 1992 Feb;70(2):77-86.

Cathinone is an alkaloid that has been discovered some fifteen years ago in the leaves of the khat bush. This plant grows in East Africa and in southern Arabia, and the inhabitants of these regions frequently chew khat because of its stimulating properties. Cathinone, which is S(-)-alpha-aminopropiophenone, was soon found to have a pharmacological profile closely resembling that of amphetamine; indeed, in a wide variety of in vitro and in vivo experiments it was demonstrated that Cathinone shares the action of amphetamine on CNS as well as its sympathomimetic effects; thus, for example, drug-conditioned animals will not distinguish between Cathinone and amphetamine. These various observations were confirmed by a clinical experiment showing that Cathinone also in humans produces amphetamine-like objective and subjective effects. Finally, it was demonstrated that Cathinone operates through the same mechanism as amphetamine, i.e. it acts by releasing catecholamines from presynaptic storage sites. Thus, much experimental evidence indicates that Cathinone is the main psychoactive constituent of the khat leaf and that, in fact, this alkaloid is a natural amphetamine.

Direct and indirect cardiovascular actions of cathinone and MDMA in the anaesthetized rat.[Pubmed:25863258]

Eur J Pharmacol. 2015 Jul 5;758:142-6.

The stimulants Cathinone (from Khat leaves) and methylenedioxymeth-amphetamine (MDMA) produce adrenoceptor mediated tachycardia and vasopressor actions that may be the result of direct receptor stimulation, actions on the noradrenaline transporter, and/or displacement of noradrenaline from nerve terminals. Effects of Cathinone or MDMA were compared with those of the indirect sympathomimetic tyramine. Male Wistar rats were anaesthetized with pentobarbitone for blood pressure and heart rate recording. Some rats were sympathectomised by treatment with 6-hydroxydopamine. In the anaesthetised rat, Cathinone, MDMA and tyramine (all 0.001-1 mg/kg) produced marked tachycardia, tyramine produced marked pressor responses and MDMA produced small pressor responses. The tachycardia to Cathinone and MDMA was almost abolished by propranolol (1mg/kg). Pretreatment with cocaine (1mg/kg) did not significantly affect the tachycardia to Cathinone or MDMA, but reduced the response to tyramine. However, in sympathectomised rats, the tachycardia to Cathinone or MDMA was markedly attenuated, but the tachycardia to tyramine was only partially reduced. Blood pressure effects of tyramine and MDMA were also markedly attenuated by sympathectomy. The results demonstrate firstly that cocaine may not be the most suitable agent for assessing direct versus indirect agonism in cardiovascular studies. Secondly, the use of chemical sympathectomy achieved the desired goal of demonstrating that cardiac beta-adrenoceptor mediated actions of Cathinone and MDMA are probably largely indirect.

Coronary and aortic vasoconstriction by cathinone, the active constituent of khat.[Pubmed:15255816]

Auton Autacoid Pharmacol. 2003 Oct-Dec;23(5-6):319-26.

1. The psychostimulant constituent of khat leaves, S-(-)-Cathinone, was examined for vascular activity on the coronary vasculature of guinea-pig-isolated perfused hearts and aortic ring preparations. 2. Cathinone caused coronary vasoconstriction, negative inotropy and negative chronotropy in isolated hearts. The major metabolite of Cathinone after its ingestion, 1R.2S-(-)-norephedrine (norephedrine), also caused coronary vasoconstriction comparable with that by Cathinone. Norephedrine, however, had no effect on force or rate of cardiac contractions. 3. Cocaine (10 microm) potentiated the coronary vasoconstriction and positive inotropy by noradrenaline indicating inhibition of neuronal uptake. The vasoconstriction and negative inotropy by Cathinone, however, were not affected, indicating that its action was not via release of noradrenaline from sympathetic neurones. 4. The alpha(1)-adrenoceptor antagonist, prazosin, blocked the vasoconstriction by noradrenaline, but not that produced by Cathinone in the presence of cocaine. This indicates that the coronary vasoconstriction by Cathinone was not due to an action on alpha(1)-adrenoceptors either directly or indirectly through noradrenaline release. 5. Three repeated doses of Cathinone displayed the same coronary vasoconstrictor responses, indicating a lack of tachyphylaxis and therefore confirming that the response was unlikely to be due to indirect sympathomimetic activity through release of noradrenaline. 6. In guinea-pig aortic rings, the order of vasoconstrictor activity was: noradrenaline > norephedrine > Cathinone, with each causing approximately equivalent maximum responses. The time to reach plateau contractions was shortest for noradrenaline (5.1 +/- 0.5 min), then norephedrine (9.3 +/- 1.5 min) and Cathinone the longest (25.4 +/- 3.2 min, 335 microm dose). 7 These results indicate that Cathinone has vasoconstrictor activity which is not due to indirect or direct sympathomimetic activity. The precise mechanism for this vasoconstriction remains to be determined. The coronary vasoconstriction may explain the increased incidence of myocardial infarction in khat chewers, which may arise from coronary vasospasm.

Cathinone increases body temperature, enhances locomotor activity, and induces striatal c-fos expression in the Siberian hamster.[Pubmed:24287379]

Neurosci Lett. 2014 Jan 24;559:34-8.

Cathinone is a beta-keto alkaloid that is the major active constituent of khat, the leaf of the Catha edulis plant that is chewed recreationally in East Africa and the Middle East. Related compounds, such as methCathinone and mephedrone have been increasing in popularity as recreational drugs, resulting in the recent proposal to classify khat as a Class C drug in the UK. There is still limited knowledge of the pharmacological effects of Cathinone. This study examined the acute effects of Cathinone on core body temperature, locomotor and other behaviors, and neuronal activity in Siberian hamsters. Adult male hamsters, previously implanted with radio telemetry devices, were treated with Cathinone (2 or 5mg/kg i.p.), the behavioral profile scored and core body temperature and locomotor activity recorded by radio telemetry. At the end of the study, hamsters received vehicle or Cathinone (5mg/kg) and neuronal activation in the brain was determined using immunohistochemical evaluation of c-fos expression. Cathinone dose-dependently induced significant (p<0.0001) increases in both temperature and locomotor activity lasting 60-90min. Cathinone (2mg/kg) increased rearing (p<0.02), and 5mg/kg increased both rearing (p<0.001) and lateral head twitches (p<0.02). Both Cathinone doses decreased the time spent at rest (p<0.001). The number of c-fos immunopositive cells were significantly increased in the striatum (p<0.0001) and suprachiasmatic nucleus (p<0.05) following Cathinone, indicating increased neuronal activity. There was no effect of Cathinone on food intake or body weight. It is concluded that systemic administration of Cathinone induces significant behavioral changes and CNS activation in the hamster.

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