Editing Cathinone (section)

==History==
===Discovery===
[[Khat]] has been cultivated in the [[Horn of Africa]] and [[Arabian Peninsula]] region of the world for thousands of years. It is most commonly chewed for the [[euphoria|euphoric]] effect it produces. The active ingredient was first proposed in 1930, when [[cathine]] was identified as a predominant alkaloid in the plant.<ref name="Patel">{{cite journal | vauthors = Patel NB | title = Mechanism of action of cathinone: the active ingredient of khat (Catha edulis) | journal = East African Medical Journal | volume = 77 | issue = 6 | pages = 329–332 | date = June 2000 | pmid = 12858935 | doi = 10.4314/eamj.v77i6.46651 | doi-access = free }}</ref> Cathine was thought to be the main active ingredient in khat until the 1960s, when it was found that the amount of cathine in the khat leaves is insufficient to produce the effects observed. In 1975, the United Nations Narcotic Laboratory analyzed khat leaves from [[Yemen]], [[Kenya]] and [[Madagascar]] and found evidence of a different alkaloid, cathinone.<ref name="Patel"/> Cathinone is molecularly similar to cathine, but is much more abundant in younger plants.  This finding caused scientists to speculate that cathinone was the true active ingredient in khat.<ref name="Patel"/>

A study was conducted in 1994 to test the effects of cathinone. Six volunteers who had never chewed khat were given an active khat sample and a cathinone-free [[placebo]] sample.<ref name="Wilder">{{cite journal | vauthors = Widler P, Mathys K, Brenneisen R, Kalix P, Fisch HU | title = Pharmacodynamics and pharmacokinetics of khat: a controlled study | journal = Clinical Pharmacology and Therapeutics | volume = 55 | issue = 5 | pages = 556–562 | date = May 1994 | pmid = 7910126 | doi = 10.1038/clpt.1994.69 | s2cid = 25788465 }}</ref> The researchers analyzed the participants' moods, activity levels and blood pressure before and after consuming the khat or placebo. This analysis showed that cathinone produced amphetamine-like effects, leading the researchers to confirm that cathinone, not cathine, is the active ingredient in khat leaves.<ref name="Wilder"/>

===Cultural significance===
[[File:Qat man.jpg|thumb|left|Man chewing khat]]
Over 20 million people in the [[Arabian Peninsula]] and [[East Africa]] chew khat leaves daily.  It is an important piece of the culture and economy in this region, especially in [[Ethiopia]] (where khat is said to have originated), Kenya, [[Djibouti]], Somalia and Yemen.  Men usually chew it during parties or other social gatherings while smoking cigarettes and drinking tea.  Farmers and other workers also use khat in the afternoon to reduce fatigue and hunger as the day goes on.  It functions like the [[caffeine]] in a strong cup of coffee as an anti-fatigue drug.  Students and drivers have been known to use it to stay alert for longer periods of time.<ref name="Kirby">{{cite news| vauthors = Kirby A |title=Yemen's khat habit soaks up water |url=http://news.bbc.co.uk/2/hi/programmes/from_our_own_correspondent/6530453.stm |website=BBC News|date=7 April 2007|publisher=BBC|access-date=20 March 2015|url-status=live|archive-url= https://web.archive.org/web/20141012084142/http://news.bbc.co.uk/2/hi/programmes/from_our_own_correspondent/6530453.stm|archive-date=12 October 2014}}</ref>

In order to produce its desired effects, khat leaves should be chewed fresh.  The fresh leaves have a higher concentration of cathinone.  Waiting too long after cultivation to chew the leaf will allow the cathinone to break down into its less potent form, cathine.  Because of the need for quick chewing, it is a habit that has historically been prevalent only where the plant grows.  However, in the recent years with improvements in road and air transport, khat chewing has spread to all corners of the world.

The cultivation of khat in Yemen is a highly profitable industry for farmers.  Khat plants will grow differently depending on the climate they are grown in and each one will produce different amounts of cathinone.<ref name="Al-Motarreb">{{cite journal | vauthors = Al-Motarreb A, Baker K, Broadley KJ | title = Khat: pharmacological and medical aspects and its social use in Yemen | journal = Phytotherapy Research | volume = 16 | issue = 5 | pages = 403–413 | date = August 2002 | pmid = 12203257 | doi = 10.1002/ptr.1106 | s2cid = 9749292 }}</ref>  It generally grows best in coastal, hot climates.  In Yemen, the khat plant is named after the region in which it is grown.  The Nehmi khat plant has the highest known concentration of cathinone, 342.5&nbsp;mg/100&nbsp;g.<ref name="Al-Motarreb"/>

===Legality===
Internationally, cathinone is a [[Convention on Psychotropic Substances#Schedules of Controlled Substances|Schedule I]] drug under the [[Convention on Psychotropic Substances]].<ref name="urlwww.incb.org">{{cite web | url = http://www.incb.org/pdf/e/list/green.pdf | archive-url = https://web.archive.org/web/20120831222336/http://www.incb.org/pdf/e/list/green.pdf | archive-date = 2012-08-31 | title = List of psychotropic substances under international control | work = International Narcotics Control Board | publisher = United Nations | year = 2003 }}</ref> Circa 1993, the [[Drug Enforcement Administration|DEA]] added cathinone to the [[Controlled Substances Act]]'s Schedule I.

The sale of khat is legal in some jurisdictions, but illegal in others (see [[Khat#Regulation|Khat (Regulation)]]). [[Substituted cathinone]]s were also often used as the key ingredient of recreational drug mixes commonly known as "[[Bath salts (drug)|bath salts]]" in the United States.<ref>{{cite news |url=https://www.pbs.org/newshour/bb/science/july-dec12/bathsalts_09-20.html | archive-url = https://web.archive.org/web/20121229055853/https://www.pbs.org/newshour/bb/science/july-dec12/bathsalts_09-20.html | archive-date = 29 December 2012 |title=Synthetic Street Drug Camouflaged as Bath Salts Has Dangerous, Bizarre Effects |publisher=PBS NewsHour |date=20 September 2012 |access-date=7 December 2013 |url-status=dead }}</ref><ref>{{cite web| vauthors = Urquhart C | date =  4 September 2004 | work = The Guardian | url = https://www.theguardian.com/world/2004/sep/04/Israel | title = Drugs and dance as Israelis blot out intifada | archive-url = https://web.archive.org/web/20161108053442/https://www.theguardian.com/world/2004/sep/04/israel | archive-date = 8 November 2016 | access-date = 19 April 2015 }}</ref><ref>{{cite web | vauthors = Chai C | date = 16 April 2015 | work = Globalnews.ca | url = http://globalnews.ca/news/1942263/what-you-need-to-know-about-flakka-the-latest-drug-causing-erratic-behaviour/ | title = What you need to know about flakka, the latest drug causing erratic behaviour | archive-url = https://web.archive.org/web/20150420001955/http://globalnews.ca/news/1942263/what-you-need-to-know-about-flakka-the-latest-drug-causing-erratic-behaviour/ | archive-date = 20 April 2015 | access-date = 19 April 2015 }}</ref><ref name="Chemistry World">{{cite web |vauthors=Extance A |title=The rising tide of 'legal highs' |url=https://www.chemistryworld.com/feature/the-rising-tide-of-legal-highs/3007738.article |website=Chemistry World |access-date=3 August 2018 |language=en |archive-date=3 August 2018 |archive-url=https://web.archive.org/web/20180803224149/https://www.chemistryworld.com/feature/the-rising-tide-of-legal-highs/3007738.article |url-status=live }}</ref>

The table below shows the legality of khat and cathinone in various countries:
{| class="wikitable"
|-http://www.who.int/countries/eri/en/
! Region !! Regulation
|-
| Eritrea || Legal
|-
| Ethiopia || Legal
|-
| Somalia || Legal
|-
| Djibouti || Legal
|-
| Kenya || Khat is legal but cathinone and cathine are classified as Class C substances
|-
| South Africa || Khat is a protected plant
|-
| China || Illegal
|-
| Israel || Legal – The khat plant leaves are allowed to be chewed and beverages containing khat are legal, but it is illegal to sell pills based on cathinone extracts
|-
| Malaysia || Illegal
|-
| Saudi Arabia || Illegal
|-
| Yemen || Khat is legal but the cultivation and selling of the plant is regulated by the government
|-
| Denmark || Illegal
|-
| Finland || Illegal
|-
| France || Khat is prohibited as a stimulant
|-
| Germany || Khat is illegal but a derivative of cathinone is available upon prescription
|-
| Ireland || Illegal unless authorized
|-
| Netherlands || Cathinone and cathine have been illegal but khat was announced as illegal in 2012
|-
| Norway || Illegal
|-
| Poland || Illegal
|-
| Sweden || Illegal
|-
| Switzerland || Illegal
|-
| United Kingdom || Illegal
|-
| Canada || Illegal to obtain unless approved by a medical practitioner
|-
| United States || Illegal
|-
| Australia || Illegal
|-
| New Zealand || Illegal
|-
| Georgia || The khat plant itself is allowed to be sold and chewed, but it is illegal to sell or make beverages containing khat
|-
| Turkey || Illegal <ref>{{Cite web|url=https://www.resmigazete.gov.tr/eskiler/2011/02/20110213-4.htm|title=Başbakanlık Mevzuatı Geliştirme ve Yayın Genel Müdürlüğü|website=www.resmigazete.gov.tr}}</ref>
|-
| Bulgaria || Illegal under List I - "Plants and substances with a high risk to the public health due to their harmful effect of misuse, prohibited for use in human and veterinary medicine"<ref>{{cite web |url=http://www.mh.government.bg/media/filer_public/2015/06/19/naredba-red-za-klasifitsirane-na-rasteniyata-i-veshtestvata-kato-narkotichni-08-11-2013.pdf | title = НАРЕДБА за реда за класифициране на растенията и веществата като наркотични | language = Bulgarian | trans-title=REGULATION on the procedure for classifying plants and substances as narcotic | work = Ministry of Health | publisher = Republic of Bulgaria |access-date=2017-08-26 |url-status=live |archive-url=https://web.archive.org/web/20170827003245/http://www.mh.government.bg/media/filer_public/2015/06/19/naredba-red-za-klasifitsirane-na-rasteniyata-i-veshtestvata-kato-narkotichni-08-11-2013.pdf |archive-date=2017-08-27 }}</ref>
|}