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cephalexin tooth : "Khat goes by numerous names: Khat, qat , chat, qaadka, kus-es-salahin miraa, tohai, tschat,Abyssinian tea, African tea, African salad, and brown cows (in tablet form).

Khat is a plant whose leaves are sometimes chewed for their stimulant properties, especially among some members of East African communities.

Khat Catha edulis; Chaat; Gat; Kat; Miraa; Qat; Tschat

Catha edulis
Scientific classification
Kingdom: Plantae
Division: Magnoliophyta
Class: Magnoliopsida
Order: Celastrales
Family: Celastraceae
Genus: Catha
Species: C. edulis
Binomial name
Catha edulis
(Vahl) Forssk. ex Endl.

Khat (Catha edulis, family Celastraceae), pronounced "cot" and also known as qat, gat, chat, and miraa, is a flowering plant native to tropical East Africa. Believed to originate in Ethiopia, it is a shrub or small tree growing to 5–8 m tall, with evergreen leaves 5–10 cm long and 1–4 cm broad. The flowers are produced on short axillary cymes 4–8 cm long, each flower small, with five white petals. The fruit is an oblong three-valved capsule containing 1–3 seeds.

Qat leaves are crimson-brown and glossy but become yellow-green and leathery as they age. The leaves are up to 5 cm wide and up to 10 cm long and emit a strong aromatic smell and have astringent and slightly sweet taste (Sawair et al., 2007).

The stimulant effect of Khat is related to the cathinone content of the leaves (Kalix, 1990).

Cathinone is metabolized rapidly to cathine (norpseudoephedrine) and norephedrine, which possess weak central stimulant properties because of their less lipophilic character (Geisshüsler and Brenneisen, 1987).

Khat is of interest as it one of a few plants that are legally consumed for their
ethnopharmacological properties.

Debates over the legal status and health effects related to consumption of this plant are currently underway in many parts of the world on account of the spread of consumption from eastern Africa resulting from migration among East African communities (Klein, 200

Current Australian regulatory considerations

The current guidelines for important khat are clearly set out.

Guidance for completing Licence and Import Permit applications (Khat)

Control status

In 1965, the World Health Organization Expert Committee on Dependence-producing Drugs' Fourteenth Report noted, "The Committee was pleased to note the resolution of the Economic and Social Council with respect to khat, confirming the view that the abuse of this substance is a regional problem and may best be controlled at that level" [1]. For this reason, khat was not Scheduled under the Single Convention on Narcotic Drugs. In 1980 the World Health Organization classified khat as a drug of abuse that can produce mild to moderate psychic dependence.

Cathine is in Schedule IV and cathinone is in Schedule I of the U.S. Controlled Substance Act. The 1993 DEA rule placing cathinone in Schedule I noted that it was effectively also banning khat:

Cathinone is the major psychoactive component of the plant Catha edulis (khat). The young leaves of khat are chewed for a stimulant effect. Enactment of this rule results in the placement of any material which contains cathinone into Schedule I.

In the UK, Cathine and Cathinone are Class C drugs. The plant Catha edulis is uncontrolled. In Germany, Cathine is a controlled substance, and ownership and sale of the plant is illegal. Similar levels of control exist throughout most other European countries.

In Australia, the importation of khat is controlled under the Customs (Prohibited Imports) Regulations. Individual users may apply for several required licenses to import up to 5kgs per month for personal use

In 2003, the total number of khat annual permits was 294 and the total number of individual khat permits was 202."

"There are two types of import permits. The single use Permit to Import can only be used once and you must request a new permit for each time you wish to import khat.

Annual Permits are labelled as such and consist of two pages. Annual Permits allow you to import up to 5 kilograms once a month for up to twelve months."

In Australia, the importation of khat is subject to regulation 5 of the Customs (Prohibited Imports)Regulations 1956 and is prohibited unless the importer holds a licence and permit issued by the Office of Chemical Safety (OCS).

A request to AQIS for data on khat license permits resulted in the release of aggregate data for license permits for the period 2003-2008. Unfortunately these permits do not contain data on the volume of khat imported.

Permits are needed for importation and a licence/permit is required for the importation of khat for personal use. Khat import permits require details on whether the permit is for fresh or dried khat.

The current licensing arrangements allow for the importation of 5kg of khat under one permit each month.

Using the 2007 data, it is estimated that an average of 33 kg was imported per permit in 2007

It is possible that if permits were renewed each month, on average it suggests that each permit could be responsible for 2.8 kg of imported khat each month in 2007.

As a projection of what could have been imported using the current licensing arrangements, it is possible that the market could have risen to 33,180 kg in 2007 if every permit was used to import 5 kg each month.

The expansion of the marketplace is substantial in the Australian community.

On the basis of this evidence, if there were significant harms (eg mental health, crime and acute health) associated with khat it certainly would have become evident in health and criminological data in this time period.

For example, a rudimentary analysis of the import data suggests that in 2007, the importation of khat supported a retail market of around $2.2 million (18,380 kg producing 73,520 two hundred and fifty gram bundles at $35 a bundle).

This estimate is based on an average import weight per permit per month of 2.8 kg. The market could expand under the current regulatory regime to $3.9 million annually, if every permit was used to import the maximum amount allowed under federal regulations.

Compared to other psychoactive drug markets, this is a very small marketplace. As a comparison, the retail heroin market in Smith Street Fitzroy alone was estimated in 2000 to be 10 Khat: a literature review worth approximately $10 million annually

(Fitzgerald unpublished data).


This review of the pharmacology of khat is limited to human studies. There is a substantial literature from animal studies on khat and cathinone, which have been recently reviewed (Feyissa & Kelly, 2000.

Cultivation and uses

Khat has been grown for use as a stimulant for centuries in the Horn of Africa and the Arabian Peninsula. There, chewing khat predates the use of coffee and is used in a similar social context. Its fresh leaves and tops are chewed or, less frequently, dried and consumed as tea, in order to achieve a state of euphoria and stimulation. Due to the availability of rapid, inexpensive air transportation, the drug has been reported in London, Rome, Amsterdam, Canada, Australia and the United States. The public has become more aware of this exotic drug through media reports pertaining to the United Nations mission in Somalia, where khat use is endemic, and its role in the Persian Gulf. The khat plant is known by a variety of names, such as qat in Yemen, chat in Ethiopia, jaad in Somalia and miraa in Kenya.

Khat use has traditionally been confined to the regions where khat is grown, because only the fresh leaves have the desired stimulating effects. In recent years improved roads, off-road motor vehicles and air transport have increased the global distribution of this perishable commodity. Traditionally, khat has been used as a socializing drug, and this is still very much the case in Yemen where khat-chewing is a predominantly male habit. In other countries, khat is consumed largely by single individuals and at parties. It is mainly a recreational drug in the countries which grow khat, though it may also be used by farmers and laborers for reducing physical fatigue, and by drivers and students for improving attention. This is similar to the use of the coca leaf in South America.

Khat is used for its mild euphoric and stimulating effects. Because of its anorectic effects, khat is used by some members of the Islamic faith during Ramadan, the ninth month of the Muslim year, which is spent in fasting from sunrise to sunset. It was previously only used by Muslims in Ethiopia, forbidden to those of the Orthodox faith, though today it is gaining popularity among Christians as well.


The stimulant effect of the plant was originally attributed to cathine, a phenethylamine-type substance isolated from the plant. However, the attribution was disputed by reports showing the plant extracts from fresh leaves contained another substance more behaviorally active than cathine. In 1975, the related alkaloid cathinone was isolated, and its absolute configuration was established in 1978. Cathinone is not very stable and breaks down to produce cathine and norephedrine. These chemicals belong to the PPA (phenylpropanolamine) family, a subset of the phenethylamines related to amphetamines and the catecholamines epinephrine and norepinephrine.


According to several early studies, on average around 100–300g of khat can be chewed in a 3-4 hour khat session (Nencini & Ahmed 1989; Kalix ,1990; 1994).

The most detailed account of Khat pharmacokinetics is reported by Toennes et al., (2003). In that study, Toennes et al., (2003) conducted a pharmacokinetic study following administration of 36–59 g of khat or approximately 0.5 mg/kg body weight.

The mucosa of the mouth is thought to be the first absorption segment, where most of the active constituents are absorbed (mean ± SD 59 ± 21% for cathinone and 84 ± 6% for cathine). The extraction of the active constituents from the leaves by chewing is very effective with only 9.1 ± 4.2% remaining as a residue after chewing (Toennes et al., 2003). Similar findings were reported in Brenneisen et al (1990) who examined the pharmacokinetics of cathinone (0.6 mg/kg body weight). The second adsorptive segment is the stomach and small intestine.

Peak plasma levels of cathinone are obtained 1.5–3.5 h after the onset of chewing khat (Feyissa & Kelly, 200. After 1-hour of chewing, plasma levels range from 40 to 140 ng/ml (mean 83 ng/ml).,

Cathinone is detectable in plasma for up to 24 hours after khat consumption. The elimination half-life is 260 min (Widler et al., 1994). Metabolism of cathinone is rapid. Only 2% of administered cathinone was found unchanged in the urine (Brenneisen et al., 1986; Nencini & Ahmed, 1989).

Blood pressures are elevated for about 3 hours after 1 hour of chewing of 0.6 g/kg, about one quarter of the amount consumed in a traditional khat session (Toennes et al., 2003). This dose is comparable with a mean oral dose of 45 mg cathinone.
Cathamines are excreted in breast milk and detected in the urine of breast-fed babies 2-4 hours after ingestion (Graziani, et al., 200.

Cardiovascular effects Khat has direct effects on the cardiovascular system causing clear increases in heart rate and blood pressure in humans (Brenneisen et al., 1990).

Brenneisen et al (1990) examined the effects of cathinone (0.6 mg/kg body weight). This dose is equivalent to approximately 25% of a normal dose.

This dose produced pressor effects (increased blood pressure) over a 2-hour period consistent with the pharmacokinetic profile for cathinone. At this dose level the pressor effects whilst statistically significant are relatively mild. It is unclear to what extent these changes are dose dependent.

These findings have been reproduced in other pharmacokinetic studies that also monitored cardiovascular changes. Significant increases in systolic and diastolic blood pressures persist for between 3 and 4 hours after the onset of chewing
khat (Toennes et al 2003; Widler et al 1994).

There is evidence of increased risk of myocardial infarction among khat users (Al-Motarreb et al., 2005), however other studies show less convincing evidence
of the links between cardiac dysfunction and khat use (Al-Hebshi & Skaug 2005: p304).

Abuse potential Using a systematic framework to assess the harm of current and future drugs of abuse, Nutt et al., (2007) ranked a range of 20 psychoactive substances in terms of social harm, physical harm and dependence potential.

The ranking system positioned khat as the least harmful substance in the group of substances evaluated in the United Kingdom by a panel of experts.

Khat is not a scheduled drug in the United Kingdom. Following from the recommendation of the Advisory Council on the Misuse Of Drugs (ACMD, 2005) khat remains a nonscheduled substance in the United Kingdom.

Although the ACMD (2005) suggested that dependence on khat was likely, the nature of this dependence was compared to a dependence on caffeine. The ACMD noted that:

“ the vast majority of people who use khat do not use in a dependent fashion and there is no evidence of more widespread drug misuse amongst khat users”.
(ACMD, 2005: p22)

cephalexin treating colds : Cathinone (2-amino-1-phenyl propanone) is one of a number of alkaloids which can be extracted from the (fresh) leaves of Catha edulis (khat). However, the ACMD understands that most of the cathinones seized, and those that have been tested, are synthetic in origin.

3.2. Cathinone is structurally very similar to amphetamine (1-phenylpropan-2-amine), differing only in the functionality present at the β-carbon.

Cathinone possesses a ketone oxygen at the β-carbon; cathinone can therefore be considered as the ‘β-keto analogue’ of amphetamine

(see Figures 1 and 2).

Figure 1: The structural similarity between amphetamine (left) and cathinone (right)

3.3. Structural modifications to the 1-phenylpropan-2-amine (amphetamine)backbone have produced a range of different compounds, many of which are closely related structurally to amphetamine; these are known as the ‘amphetamines’. In a similar manner, the molecular architecture of 2-amino-1-phenyl propanone (cathinone) can be altered to produce a series
of different compounds which are closely structurally related to cathinone.

Together these are known as the ‘cathinones’ or ‘cathinone derivatives’.

3.4. The N-methyl derivative known as methcathinone or ephedrone is the cathinone analogue of methylamphetamine, while 3,4-methylene-dioxymethcathinone (methylone) is the cathinone analogue of MDMA(ecstasy); 4-methylmethcathinone (mephedrone) has no commonly used amphetamine equivalent.

3.5. The basic cathinone structure (see Figure 2) can be altered in a number of predictable ways, such as the inclusion of additional functionality to the aromatic ring (ring substitution, R4), N-alkylation (or inclusion of the nitrogen atom in a ring structure, R2 and R3), and variation of the (typically alkyl) α-carbon substituent (R1). Multiple modifications may of course be present in a single derivative; cathinones are all usually N-alkylated (or the
nitrogen is incorporated into a ring structure, typically pyrrolidine) and many also bear ring substituents.

Figure 2: Generic sites for structural variation of cathinone, detailing α and β positions 2 .

3.6. The genesis of synthetic cathinone chemistry is rooted in the synthesis of cathinone over 120 years ago. Since this time, many synthetic cathinones have been reported, the vast majority of which have not been used in a medicinal setting. However, a handful of cathinones, such as diethylpropion, bupropion and pyrovalerone have been used in
pharmaceutical preparations, and the properties of novel cathinones (such as napthylpyrovalerone (Meltzer et al., 2006)) is still an area of active research.

3.7. Bupropion (page 42) is used medically as an antidepressant and an aid to smoking cessation and is a prescribed drug, marketed under the trade name Zyban®. Although it is a ring substituted cathinone no samples of Bupropion have been encountered in forensic analysis of seizures in the UK, and there is no evidence for its misuse.

3.8. The misuse of selected synthetic cathinones is not new; methcathinone (ephedrone), originally used as an antidepressant in the former Soviet Union in the 1930’s, went on to be used recreationally there (especially during the 1970s and 1980s) and in the USA (1990s). The emergence of six synthetic cathinones in Germany was reported between 1997 and

All six substances bear an α-pyrrolidino functionality and are therefore closely related to pyrovalerone (page 41).

3.9. More recently, there have been an increasing number of reports of other synthetic cathinones encountered within the European Union. Although many of these compounds are simply β-keto analogues of well-known amphetamines, the presence of the ketone functionality often circumvents any control measures which may already be in place for the related amphetamine congeners.

Since 2006, the following cathinones have been reported in the European Union (see Table 1; for the position of the substituents R1 to R4, see Figure 2). According to data from UK forensic providers, since January 2006 six of these have been encountered in the
UK (emboldened in Table 1).

***The generic cathinone backbone (see Figure 2) possesses a chiral centre (the α-carbon
atom if R1≠H); cathinone and its derivatives can therefore exist as stereoisomers, the
potencies of which may be markedly different. Although it is the S-enantiomer of cathinone
which is found in the fresh leaves of Catha edulis, the chirality of the cathinones is not
determined during routine forensic analysis of seizures. There is, however, no evidence to
suggest that the synthetic cathinones currently available are enantiopure; it is instead likely
that they are supplied as racemic mixtures. The qualitative or quantitative differences
between the enantiomers of the non-controlled cathinones is not known.

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cephalexin treatment uti : Structure Activity Relationships

Cathinone derivatives have a range of effects (e.g. stimulant, empathogen and antidepressant).The cathinone derivatives without ring substituents (e.g. diethylpropion,methcathinone, buphedrone, N,N-dimethylcathinone) are mostly stimulants.

Most of the cathinone derivatives encountered as legal highs are ring substituted compounds with a secondary amino group (R2 = methyl or ethyl and R3 = hydrogen) or with a cyclic amino group (NR2R3 = pyrrolidino group or phthalimido group). These substances are primarily stimulants, with varying degrees of empathogenic effects (i.e. similar in effects to MDMA). Ring substituents (R4) have included alkyl, alkoxy, methylenedioxy and halide.

The side chain substituent (R1) has mostly been a single alkyl group. However there are examples with allyl (an alkenyl) and propargyl (an alkynyl)groups and also examples with a second alkyl group attached to the same carbon atom as R1, but these compounds are not within the proposed scope.

No haloalkyl substituents (e.g. trifluoromethyl –CF3 as found in piperazine derivatives) in the ring (R4) or on the side chain (R1) have been encountered or reported in the literature. However, replacement of the ring methyl group, as in mephredrone, with a trifluoromethyl group is likely to produce substances with similar activities. It is recommended therefore that haloalkyl substituents be included in the generic definition for ring substituents.

Cathinone derivatives with a primary amino group (i.e. no N-alkyl substituents) are rarely encountered, possibly because of their instability. There are only two known examples, bk-MDA (known to substitute for MDMA in rats) and cathinone (a stimulant).

The NR2R3 amino groups reported in the scientific literature have included alkylamino (R2 = alkyl, R3 = H), dialkylamino (R2 =alkyl, R3 = alkyl), the cyclic pyrrolidino group and a large number of other cyclic amines. However, for the pyrovalerone analogues an increase in size of the nitrogen containing ring from a five-membered pyrrolidine ring to a six-membered piperidine ring resulted in a substantial loss in binding potency. There are also examples of N-allyl, N-propargyl and N-cycloalkyl substituents.

The anti-depressant drug bupropion has a tertiary-butyl group on the nitrogen atom and several other substances investigated for their potential as smoking cessation drugs also have a bulky alkyl group on the nitrogen atom, e.g.tertiary-butyl, iso-propyl or cycloalkyl, or the alkyl amino group is replaced by
a cyclic piperidino group (a cyclic amino group with 6 membered ring).

Salts, stereoisomers, esters and ethers

Cathinone derivatives with the generalised structure in Figure 1, Annex A, all have an asymmetric α-carbon atom giving rise to R and S stereoisomers. With the exception of the phthalimido derivatives, all cathinone derivatives have a basic nitrogen atom and can therefore form salts.

There is no definition of esters and ethers in the Misuse of Drugs Act 1971,but from a chemical perspective esters usually only applies to derivatives of acids with a hydroxyl group, and derivatives of alcohols and phenols.

Likewise ethers usually only applies to derivatives of alcohols and phenols.

On this basis the cathinone derivatives would not form esters or ethers.

However, keto compounds, R1R2C=O, can form ketals, R1R2C(OR’)2, which arguably might be described as a special form of an ether. Ketals of cathinone derivatives have been discussed on drug forums in the context of a pro-drug and are mentioned in the scientific literature, usually as a means of protecting the keto group during chemical syntheses.

Generic definition for the control of cathinone derivatives

Any compound (not being bupropion or a substance for the time being specified in paragraph 2.2) structurally derived from 2-amino-1-phenyl-1-propanone by modification in any of the following ways, that is to say,

(i)by substitution in the phenyl ring to any extent with alkyl, alkoxy,alkylenedioxy, haloalkyl or halide substituents, whether or not further substituted in the phenyl ring by one or more other univalent

(ii)by substitution at the 3-position with an alkyl substituent;

(iii)by substitution at the nitrogen atom with alkyl or dialkyl groups, or by inclusion of the nitrogen atom in a cyclic structure.

• the parent compound is cathinone
• “any” is taken to mean one or more Comments
This is a definition that includes all permutations for the three substitution
areas, i.e. in the ring (R4), in the side chain (R1) and on the nitrogen (NR2R3).
• All the cathinone derivatives would be in the same Class which would
result in some anomalies for compounds already controlled.
• Includes all the compounds in Appendix 1.
• Includes primary amines without ring substituents (no known examples,
except cathinone which is not included within the scope of this definition).
• Includes ring substituted primary amines (bk-MDA is the only example).
• The term “cyclic structure” has a very wide scope (e.g. all ring sizes, all
heterocyclic nitrogen compounds and structures with ring substituents).

cephalexin treatments : So, are these posts copy-pasted information from copyrighted sources?

cephalexin trigger imha : I think that the numbered bulletpoints are probably a little advanced and technical for most people, people who don't understand what a cathinone is aren't going to be helped by systematic nomenclature.


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