Khellin

Title: Khellin
CAS Registry Number: 82-02-0
CAS Name: 4,9-Dimethoxy-7-methyl-5H-furo[3,2-g][1]benzopyran-5-one
Additional Names: 5,8-dimethoxy-2-methyl-4¢,5¢-furo-6,7-chromone; 5,8-dimethoxy-2-methyl-6,7-furanochromone; 4,9-dimethoxy-7-methyl-5-oxofuro[3,2-g]-1,2-chromene; 4,9-dimethoxy-7-methyl-5-oxo-1,8-dioxabenz[f]indene; visammin
Trademarks: Ammivin; Lynamine (Memphis); Vasokellina (Angelini)
Molecular Formula: C14H12O5
Molecular Weight: 260.24
Percent Composition: C 64.61%, H 4.65%, O 30.74%
Literature References: Found in seeds of Ammi visnaga Lam., Umbelliferae; one of the active principles of the Egyptian traditional medicine known as "khella." See also: visnadine, visnagin. Isoln and structure: Späth, Gruber, Ber. 71, 106 (1938). Synthesis: Baxter et al., J. Chem. Soc. 1949, S 30; Gardner et al., J. Org. Chem. 15, 841 (1950); Schönberg, Sina, J. Am. Chem. Soc. 72, 1611, 3396 (1950); M. W. Reed, H. W. Moore, J. Org. Chem. 53, 4166 (1988). Crystal structure: J. P. Beale, Cryst. Struct. Commun. 2, 125 (1973). Toxicity data: E. Busch et al., Arzneim.-Forsch. 11, 915 (1961). GC determn in serum: A. S. Carlin et al., J. Chromatogr. 614, 324 (1993). Clinical evaluation in vitiligo: B. Ortel et al., J. Am. Acad. Dermatol. 18, 693 (1988). Comprehensive description: M. A. Hassan, M. U. Zubai, Anal. Profiles Drug Subs. 9, 371-396 (1980).
Properties: Crystals from methanol. Bitter taste. mp 154-155°. bp0.05 180-200°. uv max (alc): 250, 338 nm (E1%1cm 1600, 200). Soly in g/100 ml at 25°: water 0.025; acetone 3.0; methanol 2.6; isopropanol 1.25; ether 0.5. Much more sol in hot water and hot methanol. LD50 in mice, rats (mg/kg): 30.6, 34.4 i.v.; 50.8, 68.8 orally (Busch).
Melting point: mp 154-155°
Boiling point: bp0.05 180-200°
Absorption maximum: uv max (alc): 250, 338 nm (E1%1cm 1600, 200)
Toxicity data: LD50 in mice, rats (mg/kg): 30.6, 34.4 i.v.; 50.8, 68.8 orally (Busch)
Therap-Cat: Vasodilator (coronary). Photosensitizer in treatment of vitiligo.
Keywords: Vasodilator (Coronary).
Khellol Glucoside Kiku Oil Kininogens Kinoprene Kistrin

Khellin
Khellin
Ball-and-stick model
Identifiers
CAS number 82-02-0 YesY
PubChem 3828
KEGG C09010 N
ChEMBL CHEMBL44746 N
Jmol-3D images Image 1
Properties
Molecular formula C14H12O5
Molar mass 260.24 g mol−1
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Khellin is a furanochromone, an organic compound which is derivative of chromone (1,4-benzopyrone) and furan. It has lipophilic properties and causes vasodilation (widening of blood vessels). It is found in the plant Ammi visnaga which has been used in Egyptian folk medicine.

In Egypt, the plant "Khella" was used for renal colic. The incidence of renal colic was due mostly to schistosomiasis infections and stone formation. The plant mixture had diuretic properties that were seen to relieve renal colic in Egyptian folk medicine. After the chemical compound khellin was identified, people began to study its properties. It was found to relax the ureter and coronary arteries.

It is not used as a systemic medication because it is difficult to absorb and causes a range of undesirable side effects such as dizziness, headache, gastrointestinal disorders and nausea. However, it has been used successfully to treat vitiligo by topical application.[citation needed] In the early 20th century, researchers searched for khellin analogs with lower toxicity and better efficacy. A number of drugs were discovered through this research and amiodarone and cromolyn sodium are khellin analogs used in current medical practice.