Lactucopicrin

Lactucopicrin (Intybin) is a bitter substance that has a sedative and analgesic effect,^[1] 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.^[2] It is also found in dandelion coffee.

Quick facts Names, Identifiers ...

Lactucopicrin

Names
Preferred IUPAC name [(3aR,4S,9aS,9bR)-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
Other names Intybin
Identifiers
CAS Number	6466-74-6 (3aR,4S,9bS)
3D model (JSmol)	Interactive image
ChemSpider	152483 (3aR,4S,9bS)
MeSH	Intybin
PubChem CID	174863 (3aR,4S,9bS)
UNII	SKG846KJ3G Y
CompTox Dashboard (EPA)	DTXSID90983277
InChI InChI=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 Key: QCDLLIUTDGNCPO-AEMJNJESSA-N 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 Key: QCDLLIUTDGNCPO-AEMJNJESBM
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
Properties
Chemical formula	C23H22O7
Molar mass	410.422 g·mol−1
Pharmacology
Routes of administration	Oral, Smoked
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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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.^[3] Lactucopicrin has also been shown to act as an acetylcholinesterase inhibitor.^[4]