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			{{more medical citations needed|date=April 2016}}
			<!-- EDIT BELOW THIS LINE -->
	{{Chembox		{{Chembox
			| Verifiedfields = changed
⚫	| verifiedrevid = 396746457
			| Watchedfields = changed
		⚫	| verifiedrevid = 415684280
	| ImageFile1 = Khellin.png		| ImageFile1 = Khellin.png
	| ImageSize1 = 200px
	| ImageName1 = Khellin		| ImageName1 = Khellin
	| ImageFile2 = Khellin_3D.png		| ImageFile2 = Khellin_3D.png
		⚫	| ImageName2 = Ball-and-stick model
	| ImageSize2 = 200px
		⚫	| PIN = 4,9-Dimethoxy-7-methyl-5''H''-furobenzopyran-5-one
⚫	| ImageName2 = Ball-and-stick model
			| OtherNames = amicardine, corafurone, methafrone, kelourin, rykellin, visammin; ammispasmin, ammivisnagen, gynokhellan, interkellin, interkhellin, amikellin, ammipuran, benecardin, deltoside, kelicorin, khelangin, khellamine, khellanals, khellinorm, medekellin, visammimix, viscardan, visnagalin, kalangin, kelincor
⚫	| IUPACName = 4,9-Dimethoxy-7-methylfurochromen-5-one
		⚫	|Section1={{Chembox Identifiers
	| SystematicName =
			| CASNo_Ref = {{cascite|correct|??}}
	| OtherNames = Amicardine<br>Corafurone<br>Methafrone<br>Kelourin<br>Rykellin<br>Visammin <br>Ammispasmin<br>Ammivisnagen<br>Gynokhellan<br>Interkellin<br>Interkhellin<br>Amikellin<br>Ammipuran<br>Benecardin<br>Deltoside<br>Kelicorin<br>Khelangin<br>Khellamine<br>Khellanals<br>Khellinorm<br>Medekellin<br>Visammimix<br>Viscardan<br>Visnagalin<br>Kalangin<br>Kelincor
⚫	| Section1 = {{Chembox Identifiers
	| CASNo = 82-02-0		| CASNo = 82-02-0
			| UNII_Ref = {{fdacite|changed|FDA}}
			| UNII = 5G117T0TJZ
	| PubChem = 3828		| PubChem = 3828
			| KEGG_Ref = {{keggcite|changed|kegg}}
			| KEGG = C09010
			| ChEMBL_Ref = {{ebicite|changed|EBI}}
			| ChEMBL = 44746
	| SMILES = O(C)c1c2C=COc2c(OC)c3OC(C)=CC(=O)c13		| SMILES = O(C)c1c2C=COc2c(OC)c3OC(C)=CC(=O)c13
			| EINECS = 201-392-8
⚫	}}
			| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
⚫	| Section2 = {{Chembox Properties
			| ChemSpiderID = 3696
	| Formula = C<sub>14</sub>H<sub>12</sub>O<sub>5</sub>
			| InChI = 1/C14H12O5/c1-7-6-9(15)10-11(16-2)8-4-5-18-12(8)14(17-3)13(10)19-7/h4-6H,1-3H3
	| MolarMass = 260.24 g/mol
			| InChIKey = HSMPDPBYAYSOBC-UHFFFAOYAZ
	| Appearance =
			| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
⚫	| Density =
			| StdInChI = 1S/C14H12O5/c1-7-6-9(15)10-11(16-2)8-4-5-18-12(8)14(17-3)13(10)19-7/h4-6H,1-3H3
⚫	| MeltingPt =
			| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
⚫	| BoilingPt =
			| StdInChIKey = HSMPDPBYAYSOBC-UHFFFAOYSA-N
⚫	| Solubility = }}
			| RTECS =
⚫	| Section3 = {{Chembox Hazards
	| MainHazards =		| MeSHName = C438920
		⚫	}}
⚫	| FlashPt =
		⚫	|Section2={{Chembox Properties
	| Autoignition = }}
			| C=14 | H=12 | O=5
			| Appearance = colorless needle-shaped crystals
		⚫	| Density =
		⚫	| MeltingPt = 154-155 C
		⚫	| BoilingPt =
		⚫	| Solubility =
			}}
		⚫	|Section3={{Chembox Hazards
			| MainHazards =
		⚫	| FlashPt =
			| AutoignitionPt =
			}}
	}}		}}
			'''Khellin''' has been used as an herbal ], with use in the Mediterranean dating back to Ancient Egypt, to treat a variety of maladies including: ], ], ], ], ], and ].<ref>{{cite journal|last1=Azim Khan|first1=Muhammad|title=Phytochemistry and Medicinal Properties of Ammi Visnaga|journal=Pak. J. Bot.|date=2014|volume=46|issue=3|pages=861–867}}</ref> It is a major constituent of the plant '']'', also known as ''Ammi visnaga'' and as bishop's weed. Once purified, khellin exists as colorless, odorless, bitter-tasting needle-shaped crystals<ref>{{cite journal|last1=Shinde|first1=P B|last2=Laddha|first2=K S|title=Development of new isolation technique and validated HPLC method development for khellin|journal=Indian Journal of Natural Products and Resources|date=March 2014|volume=5|issue=1|pages=40–43}}</ref> and is classified as a gamma-pyrone, a ] derivative. In the early 20th century, researchers searched for khellin analogs with lower ] and better ]. A number of drugs were discovered through this research, such as ] and ], which are used in current medical practice. ] is also mentioned as analog.<ref name="DewarHorler1959">{{cite journal|last1=Dewar|first1=H. A.|last2=Horler|first2=A. R.|last3=Newell|first3=D. J.|title=A Clinical Trial of Penta-Erythritol Tetranitrate, A Khellin Derivative (Recordil), and Iproniazid in Angina of Effort|journal=Heart|volume=21|issue=3|year=1959|pages=315–322|issn=1355-6037|doi=10.1136/hrt.21.3.315|pmc=1017586|pmid=13816307}}</ref>
	'''Khellin''' is a ], an organic compound which is derivative of chromone (1,4-benzopyrone) and furan.
			==Background==
	It has ] properties and causes ] (widening of blood vessels). It is found in the plant '']'' which has been used in Egyptian ].
			Khellin is found in Egypt, the Middle East, and areas surrounding the Mediterranean. It is a major constituent of the plant ''Visnaga daucoides'', existing between 0.3 and 1.2% in the leaves and seeds.<ref>{{cite journal|last1=Mesbah|first1=M.K.|title=Determination of Khellin and Visnagin in Ammi visnaga fruits and in renal teas by HPLC|journal=Egypt. J. Pharm. Sci.|date=1992|volume=33|issue=5–6|pages=897–904}}</ref> "Bishop's weed" is a name given to several species of plants; however, only ''Visnaga daucoides'' contains khellin. Khellin is rarely found in its pure form; instead it is found in ''Visnaga daucoides'' or "khella" extract. As a result, many healing properties have been attributed to khellin that are actually due to other constituents of the extract.
			''Visnaga daucoides'' preparations are commercially available and very common; however, the amount of khellin and other ingredients varies greatly between brands and even batches of the same brand. The extract is commonly found as a tea or in a pill form.
			==Medical use==
	It is not used as a medication because it is difficult to absorb and causes a range of undesirable side effects such as dizziness, headache, gastrointestinal disorders and nausea.
			Therapeutic use is often not recommended, as the risks often outweigh the benefits. Regardless of this recommendation, ''Visnaga daucoides'' is still often used in the Middle East, Egypt, and surrounding areas. Unwanted side effects include dizziness, reversible ], pseudoallergic reaction, and elevated levels of liver enzymes (transaminases and ]).<ref>{{cite book|last1=Blumenthal|first1=M|last2=Busse|first2=W.R.|last3=Goldberg|first3=A.|last4=Gruenwald|first4=J.|last5=Hall|first5=T.|last6=Riggins|first6=C.W.|last7=Rister|first7=R.S|title=The complete German commission monographs, therapeutic guide to herbal medicines|date=1998}}</ref>
			===Vitiligo===
⚫	In Egypt, the plant "Khella" was used for ]. The incidence of renal colic was due mostly to ] infections and ] formation. The plant mixture had ] properties that were seen to relieve renal colic in Egyptian ]. After the ] khellin was identified, people began to study its properties. It was found to relax the ] and ].
			Vitiligo is a disease which causes loss of pigmentation in portions of skin. When khellin is applied topically in combination with UVA light, it is able to stimulate ] (cells that produce melanin) in hair follicles for successful treatment of vitiligo. One such method is blister roof transplantation; in which, blisters are formed on an unaffected area and are then grafted onto a vitiligo affected area. When khellin is applied topically and treated with UV light, pigmentation returns to treated areas.<ref>{{cite journal|last1=Leeuw|first1=J de|last2=Assen|first2=YJ|last3=Bjerring|first3=P|last4=Neumann|first4=HA Martino|title=Treatment of vitiligo with khellin liposomes, UV light and blister roof transplantation|journal=J Eur Acad Dermatol Venereol|date=2011|volume=25|issue=1|pages=74–81|doi=10.1111/j.1468-3083.2010.03701.x|pmid=20477914|s2cid=20632501 }}</ref>
			When taken systemically, khellin induces elevated liver enzyme levels and broad photosensitivity; however, topical application reduces these side effects. ] are commonly used for vitiligo treatment, but have higher phototoxic and DNA mutagenic effects. While khellin treatment in conjunction with UV therapy is successful, accelerated photoaging and increased risk of skin cancer is another concern.<ref>{{cite journal|last1=Plettenberg|first1=Heidi|last2=Assmann|first2=Till|last3=Ruzicka|first3=Thomas|title=Childhood vitiligo and tacrolimus|journal=Arch. Dermatol.|date=2003|volume=139|issue=5|pages=651–654|doi=10.1001/archderm.139.5.651|pmid=12756103}}</ref>
			===Kidney stones===
	In the early 20th century, researchers searched for khellin analogues with lower ] and better ]. A number of drugs were discovered in researching khellin analogues. ] and ] are khellin analogues used in current medical practice.
			When ''Visnaga daucoides'' extract is taken daily, as a tea or as a pill, ] ] formation is inhibited, making it a good treatment for ] (a condition in which there is excessive oxalate excretion in the urine, causing kidney stones). Khellin was thought to slow or prevent calcium oxalate nucleation, preventing stones from forming. However, studies have shown that khellin is not the active ingredient in ''Visnaga daucoides'' extract. Upon studying calcium oxalate nucleation, ''Visnaga daucoides'' extract as a whole was shown to prolong nucleation time as well as change stone conformation, while khellin alone had no effect.<ref>{{cite journal|last1=Vanachayangkul|first1=P.|last2=Chow|first2=N.|last3=Khan|first3=S. R.|last4=Butterweck|first4=Veronika|title=Prevention of renal crystal deposition by an extract of Ammi visnaga L. and its constituents khellin and visnagin in hyperoxaluric rats|journal=Urol. Res.|date=2011|volume=39|issue=3|pages=189–195|doi=10.1007/s00240-010-0333-y|pmid=21069311|pmc=3663934}}</ref><ref>{{cite journal|last1=Abdel-Aal|first1=E.A.|last2=Daosukho|first2=S.|last3=El-Shall|first3=H.|title=Effect of supersaturation ratio and Khella extract on nucleation and morphology of kidney stones|journal=Journal of Crystal Growth|date=2009|volume=311|issue=9|pages=2673–2681|doi=10.1016/j.jcrysgro.2009.02.027|bibcode=2009JCrGr.311.2673A }}</ref>
		⚫	Khellin has also been used to treat renal colic, which is due mostly to ] infections and ] formation. The plant mixture had ] properties that were seen to relieve renal colic by relaxing the ] and acting as a ].
⚫	==See also==
⚫	* ]
			===Other===
			Intramuscular injections of khellin can also be used to treat asthma. Khellin acts as a bronchodilator; however, the common side effects including nausea present difficulties.<ref>{{cite journal|last1=Kennedy|first1=M.C.S|last2=Stock|first2=J.P.P|title=The bronchodilator action of khellin|journal=Thorax|date=1952|volume=7|issue=1|pages=43–65|doi=10.1136/thx.7.1.43|pmc=1019140|pmid=14913500}}</ref>
			Khellin has been used to relieve the pain associated with ] by acting as a selective coronary vasodilator.<ref>{{cite journal|last1=Osher|first1=Harold|last2=Katz|first2=Kermit|last3=Wagner|first3=Donald|title=Khellin in the treatment of angina pectoris|journal=The New England Journal of Medicine|date=1951|volume=244|issue=9|pages=315–321|doi=10.1056/nejm195103012440901|pmid=14806755}}</ref> This can be done either orally or intramuscularly; however nausea is a major side effect regardless of how the medication is taken.<ref>{{cite journal|last1=Conn|first1=James J.|title=The treatment of angina pectoris with khellin|journal=Annals of Internal Medicine|date=1952|volume=36|issue=5|pages=1173–1178|doi=10.7326/0003-4819-36-5-1173|pmid=14924454}}</ref>
		⚫	== See also ==
		⚫	* ]
	* ], an antimitotic drug		* ], an antimitotic drug
			* ]
	==External links==		== References ==
			{{reflist}}
			== External links ==
	*		*
	*		*
		⚫	]
	{{Furanochromone}}
			]
	]		]
⚫	]
	]
	]