{{Chembox | Watchedfields = changed | ImageFile = Lactucopicrin.png | ImageClass = skin-invert-image | ImageSize = 240px | ImageName = Stereo wireframe of a chiral lactucopicrin tautomer | PIN = [(3a''R'',4''S'',9a''S'',9b''R'')-4-Hydroxy-6-methyl-3-methylidene-2,7-dioxo-2,3,3a,4,5,7,9a,9b-octahydroazuleno[4,5-''b'']furan-9-yl]methyl (4-hydroxyphenyl)acetate | OtherNames = Intybin |Section1={{Chembox Identifiers | CASNo = 6466-74-6 | CASNo_Comment = (3a''R'',4''S'',9b''S'') | UNII_Ref = {{fdacite|correct|FDA}} | UNII = SKG846KJ3G | PubChem = 174863 | PubChem_Comment = (3a''R'',4''S'',9b''S'') | ChemSpiderID = 152483 | ChemSpiderID_Comment = (3a''R'',4''S'',9b''S'') | MeSHName = Intybin | SMILES = CC1=C2[C@@H]([C@@H]3[C@@H]([C@H](C1)O)C(=C)C(=O)O3)C(=CC2=O)COC(=O)Cc4ccc(cc4)O | InChI = 1/C23H22O7/c1-11-7-16(25)20-12(2)23(28)30-22(20)21-14(9-17(26)19(11)21)10-29-18(27)8-13-3-5-15(24)6-4-13/h3-6,9,16,20-22,24-25H,2,7-8,10H2,1H3/t16-,20+,21-,22-/m0/s1 | InChIKey = QCDLLIUTDGNCPO-AEMJNJESBM | StdInChI = 1S/C23H22O7/c1-11-7-16(25)20-12(2)23(28)30-22(20)21-14(9-17(26)19(11)21)10-29-18(27)8-13-3-5-15(24)6-4-13/h3-6,9,16,20-22,24-25H,2,7-8,10H2,1H3/t16-,20+,21-,22-/m0/s1 | StdInChIKey = QCDLLIUTDGNCPO-AEMJNJESSA-N}} |Section2={{Chembox Properties | C=23 | H=22 | O=7 }} |Section3={{Chembox Pharmacology | AdminRoutes = Oral, Smoked}} }}
'''Lactucopicrin''' ('''Intybin''') is a bitter substance that has a sedative and analgesic effect,<ref>{{cite journal | last1 = Wesołowska | first1 = A | last2 = Nikiforuk | first2 = A | last3 = Michalska | first3 = K | last4 = Kisiel | first4 = W | last5 = Chojnacka-Wójcik | first5 = E | date = Sep 2006 | title = Analgesic and sedative activities of lactucin and some lactucin-like guaianolides in mice | journal = Journal of Ethnopharmacology | volume = 107 | issue = 2| pages = 254–8 | doi = 10.1016/j.jep.2006.03.003 | pmid = 16621374 }}</ref> acting on the central nervous system. It is a sesquiterpene lactone, and is a component of lactucarium, derived from the plant ''Lactuca virosa'' (wild lettuce), as well as being found in some related plants such as ''Cichorium intybus''.<ref>{{cite journal | last1 = Sessa | first1 = RA | last2 = Bennett | first2 = MH | last3 = Lewis | first3 = MJ | last4 = Mansfield | first4 = JW | last5 = Beale | first5 = MH | date = Sep 2000 | title = Metabolite profiling of sesquiterpene lactones from Lactuca species. Major latex components are novel oxalate and sulfate conjugates of lactucin and its derivatives | journal = Journal of Biological Chemistry | volume = 275 | issue = 35| pages = 26877–84 | pmid = 10858433 | doi=10.1074/jbc.M000244200| doi-access = free }}</ref> It is also found in dandelion coffee.
As well as their traditional use as sedatives and analgesics, these plants have also been used as antimalarials, and both lactucin and lactucopicrin have demonstrated antimalarial effects ''in vitro''.<ref>{{cite journal | last1 = Bischoff | first1 = TA | last2 = Kelley | first2 = CJ | last3 = Karchesy | first3 = Y | last4 = Laurantos | first4 = M | last5 = Nguyen-Dinh | first5 = P | last6 = Arefi | first6 = AG | year = 2004 | title = Antimalarial activity of lactucin and lactucopicrin: sesquiterpene lactones isolated from Cichorium intybus L. | journal = Journal of Ethnopharmacology | volume = 95 | issue = 2–3| pages = 455–7 | doi = 10.1016/j.jep.2004.06.031 | pmid = 15507374 }}</ref> Lactucopicrin has also been shown to act as an acetylcholinesterase inhibitor.<ref>{{cite journal | last1 = Rollinger | first1 = JM | last2 = Mocka | first2 = P | last3 = Zidorn | first3 = C | last4 = Ellmerer | first4 = EP | last5 = Langer | first5 = T | last6 = Stuppner | first6 = H | year = 2005 | title = Application of the in combo screening approach for the discovery of non-alkaloid acetylcholinesterase inhibitors from Cichorium intybus | journal = Current Drug Discovery Technologies | volume = 2 | issue = 3| pages = 185–93 | pmid = 16472227 | doi=10.2174/1570163054866855}}</ref>
== See also == * Lactucin
== References == <references/>
{{Acetylcholine metabolism and transport modulators}}
Category:Acetylcholinesterase inhibitors Category:Sesquiterpene lactones Category:4-Hydroxyphenyl compounds Category:Enones Category:Lactones Category:Azulenofurans Category:Acetate esters Category:Cyclopentenes Category:Vinylidene compounds