# Lactucopicrin
> Mediated Wiki article. Canonical URL: https://mediated.wiki/source/Lactucopicrin
> Markdown URL: https://mediated.wiki/source/Lactucopicrin.md
> Source: https://en.wikipedia.org/wiki/Lactucopicrin
> Source revision: 1330319481
> License: Creative Commons Attribution-ShareAlike 4.0 International (https://creativecommons.org/licenses/by-sa/4.0/)
{{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](/source/sedative) and [analgesic](/source/analgesic) effect,[{{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 }}] acting on the [central nervous system](/source/central_nervous_system). It is a [sesquiterpene lactone](/source/sesquiterpene_lactone), and is a component of [lactucarium](/source/lactucarium), derived from the plant ''[Lactuca virosa](/source/Lactuca_virosa)'' (wild lettuce), as well as being found in some related plants such as ''[Cichorium intybus](/source/Cichorium_intybus)''.[{{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 }}] It is also found in [dandelion coffee](/source/dandelion_coffee).
As well as their traditional use as sedatives and analgesics, these plants have also been used as [antimalarials](/source/Antimalarial_drug), and both lactucin and lactucopicrin have demonstrated antimalarial effects ''in vitro''.[{{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 }}] Lactucopicrin has also been shown to act as an [acetylcholinesterase inhibitor](/source/acetylcholinesterase_inhibitor).[{{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}}]
== See also ==
* [Lactucin](/source/Lactucin)
== 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
---
Adapted from the Wikipedia article [Lactucopicrin](https://en.wikipedia.org/wiki/Lactucopicrin) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Lactucopicrin?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.