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Lactucopicrin information


Lactucopicrin
Stereo wireframe of a chiral lactucopicrin tautomer
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 checkY
CompTox Dashboard (EPA)
  • DTXSID90983277 Edit this at Wikidata
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

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.

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]

  1. ^ Wesołowska, A; Nikiforuk, A; Michalska, K; Kisiel, W; Chojnacka-Wójcik, E (Sep 2006). "Analgesic and sedative activities of lactucin and some lactucin-like guaianolides in mice". Journal of Ethnopharmacology. 107 (2): 254–8. doi:10.1016/j.jep.2006.03.003. PMID 16621374.
  2. ^ Sessa, RA; Bennett, MH; Lewis, MJ; Mansfield, JW; Beale, MH (Sep 2000). "Metabolite profiling of sesquiterpene lactones from Lactuca species. Major latex components are novel oxalate and sulfate conjugates of lactucin and its derivatives". Journal of Biological Chemistry. 275 (35): 26877–84. doi:10.1074/jbc.M000244200. PMID 10858433.
  3. ^ Bischoff, TA; Kelley, CJ; Karchesy, Y; Laurantos, M; Nguyen-Dinh, P; Arefi, AG (2004). "Antimalarial activity of lactucin and lactucopicrin: sesquiterpene lactones isolated from Cichorium intybus L.". Journal of Ethnopharmacology. 95 (2–3): 455–7. doi:10.1016/j.jep.2004.06.031. PMID 15507374.
  4. ^ Rollinger, JM; Mocka, P; Zidorn, C; Ellmerer, EP; Langer, T; Stuppner, H (2005). "Application of the in combo screening approach for the discovery of non-alkaloid acetylcholinesterase inhibitors from Cichorium intybus". Current Drug Discovery Technologies. 2 (3): 185–93. doi:10.2174/1570163054866855. PMID 16472227.

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Lactucopicrin

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Lactucopicrin (Intybin) is a bitter substance that has a sedative and analgesic effect, acting on the central nervous system. It is a sesquiterpene lactone...

Word Count : 281

Lactucarium

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activity include lactucin and its derivatives lactucopicrin and 11β,13-dihydrolactucin. Lactucin and lactucopicrin were found to have analgesic effects comparable...

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Lactuca virosa

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discovered two chemicals responsible for the properties of L. virosa; lactucopicrin and lactucin. In the United States, the plant experienced a resurgence...

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Sesquiterpene lactone

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found in Artemisia annua. Lactucin, desoxylactucin, lactucopicrin, lactucin-15-oxalate, lactucopicrin-15-oxalate are some of the most prominent found in...

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Lactucin

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shown some antimalarial effects. It is also found in dandelion coffee. Lactucopicrin Wesołowska A, Nikiforuk A, Michalska K, Kisiel W, Chojnacka-Wójcik E...

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Dandelion coffee

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11-dihydrotaraxinic acid and 13-dihydrotaraxinic acid l'-glucoside Lactucopicrin Lactucin Cichorin Eudesmanolides Tetrahydroridentin-B Taraxacolide-O-β-glucopyranoside...

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Acetylcholinesterase inhibitor

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tetrahydroaminoacridine (THA) Edrophonium Huperzine A Ladostigil Ungeremine Lactucopicrin Acotiamide Hybrid/bitopic ligands Compounds which function as quasi-irreversible...

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Caffeine

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Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol...

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Chicory

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bitterness are primarily the two sesquiterpene lactones, lactucin and lactucopicrin. Other components are aesculetin, aesculin, cichoriin, umbelliferone...

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Tetrahydrocannabinol

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Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol...

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Anticholinergic

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Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol...

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Donepezil

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Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol...

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Acetylcholine

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Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol...

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Choline

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Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol...

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Itopride

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Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol...

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Nerve agent

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Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol...

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Botulinum toxin

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Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol...

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Novichok

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Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol...

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Physostigmine

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Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol...

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Carbendazim

Last Update:

Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol...

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Neostigmine

Last Update:

Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol...

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Pyridostigmine

Last Update:

Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol...

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Rivastigmine

Last Update:

Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol...

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Galantamine

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Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol...

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Malathion

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Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol...

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Dicyclohexyl phosphorofluoridate

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Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol...

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Soman

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Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol...

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Ethylcholine mustard

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Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol...

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Cholinergic

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Corydaline Corynoline Crimidine Cyclanoline Cymserine Harmaline Kobophenol A Lactucopicrin Lycorine Phosacetim Rosmarinic acid Stercuronium iodide Taspine Tetrahydrocannabinol...

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