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Dicentrine
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| Names
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Preferred IUPAC name
(7aS)-10,11-Dimethoxy-7-methyl-6,7,7a,8-tetrahydro-2H,5H-benzo[g][1,3]benzodioxolo[6,5,4-de]quinoline |
| Other names
(S)-(+)-Dicentrine
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| Identifiers
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| ChemSpider
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| UNII
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InChI=1S/C20H21NO4/c1-21-5-4-11-7-17-20(25-10-24-17)19-13-9-16(23-3)15(22-2)8-12(13)6-14(21)18(11)19/h7-9,14H,4-6,10H2,1-3H3/t14-/m0/s1 Key: YJWBWQWUHVXPNC-AWEZNQCLSA-N
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CN1CCc2cc3c(c-4c2[C@@H]1Cc5c4cc(c(c5)OC)OC)OCO3
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| Properties
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C20H21NO4
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| Molar mass
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339.391 g·mol−1
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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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Tracking categories (test):
Dicentrine is an aporphinic alkaloid found in several plant species, mainly from family Lauraceae, including Lindera megaphylla.[1] At high doses, dicentrine shows antinociceptive activity in a mouse model of pain.[2] It probably acts via a TRPA1-dependent mechanism.[2]
References
- ↑ Huang, Ray-Ling; Chen, Chien-Chih; Huang, Yu-Lin; Ou, Jun-Chih; Hu, Cheng-Po; Chen, Chieh-Fu; Chang, Chungming (1998). "Anti-Tumor Effects of d-Dicentrine from the Root of Lindera megaphylla". Planta Medica 64 (3): 212–215. doi:10.1055/s-2006-957411. PMID 9581516.
- ↑ 2.0 2.1 Montrucchio, Deise Prehs; Córdova, Marina Machado; Santos, Adair Roberto Soares (2013-07-04). "Plant Derived Aporphinic Alkaloid S-(+)-Dicentrine Induces Antinociceptive Effect in Both Acute and Chronic Inflammatory Pain Models: Evidence for a Role of TRPA1 Channels". PLOS ONE 8 (7): e67730. doi:10.1371/journal.pone.0067730. ISSN 1932-6203. PMID 23861794. Bibcode: 2013PLoSO...867730M.
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| TRPA | | Activators |
- 4-Hydroxynonenal
- 4-Oxo-2-nonenal
- 4,5-EET
- 12S-HpETE
- 15-Deoxy-Δ12,14-prostaglandin J2
- α-Sanshool (ginger, Sichuan and melegueta peppers)
- Acrolein
- Allicin (garlic)
- Allyl isothiocyanate (mustard, radish, horseradish, wasabi)
- AM404
- Bradykinin
- Cannabichromene (cannabis)
- Cannabidiol (cannabis)
- Cannabigerol (cannabis)
- Cinnamaldehyde (cinnamon)
- CR gas (dibenzoxazepine; DBO)
- CS gas (2-chlorobenzal malononitrile)
- Curcumin (turmeric)
- Dehydroligustilide (celery)
- Diallyl disulfide
- Dicentrine (Lindera spp.)
- Farnesyl thiosalicylic acid
- Formalin
- Gingerols (ginger)
- Hepoxilin A3
- Hepoxilin B3
- Hydrogen peroxide
- Icilin
- Isothiocyanate
- Ligustilide (celery, Angelica acutiloba)
- Linalool (Sichuan pepper, thyme)
- Methylglyoxal
- Methyl salicylate (wintergreen)
- N-Methylmaleimide
- Nicotine (tobacco)
- Oleocanthal (olive oil)
- Paclitaxel (Pacific yew)
- Paracetamol (acetaminophen)
- PF-4840154
- Phenacyl chloride
- Polygodial (Dorrigo pepper)
- Shogaols (ginger, Sichuan and melegueta peppers)
- Tear gases
- Tetrahydrocannabinol (cannabis)
- Thiopropanal S-oxide (onion)
- Umbellulone (Umbellularia californica)
- WIN 55,212-2
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| TRPC | |
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| TRPM | |
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| TRPML | |
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| TRPP | |
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| TRPV | | Activators |
- 2-APB
- 5',6'-EET
- 9-HODE
- 9-oxoODE
- 12S-HETE
- 12S-HpETE
- 13-HODE
- 13-oxoODE
- 20-HETE
- α-Sanshool (ginger, Sichuan and melegueta peppers)
- Allicin (garlic)
- AM404
- Anandamide
- Bisandrographolide (Andrographis paniculata)
- Camphor (camphor laurel, rosemary, camphorweed, African blue basil, camphor basil)<!--TRPV1 and TRPV3-->
- Cannabidiol (cannabis)
- Cannabidivarin (cannabis)
- Capsaicin (chili pepper)
- Carvacrol (oregano, thyme, pepperwort, wild bergamot, others)
- DHEA
- Diacyl glycerol
- Dihydrocapsaicin (chili pepper)
- Estradiol
- Eugenol (basil, clove)
- Evodiamine (Euodia ruticarpa)
- Gingerols (ginger)
- GSK1016790A
- Heat
- Hepoxilin A3
- Hepoxilin B3
- Homocapsaicin (chili pepper)
- Homodihydrocapsaicin (chili pepper)
- Incensole (incense)
- Lysophosphatidic acid
- Low pH (acidic conditions)
- Menthol (mint)
- N-Arachidonoyl dopamine
- N-Oleoyldopamine
- N-Oleoylethanolamide
- Nonivamide (PAVA) (PAVA spray)
- Nordihydrocapsaicin (chili pepper)
- Paclitaxel (Pacific yew)
- Paracetamol (acetaminophen)
- Phorbol esters (e.g., 4α-PDD)
- Piperine (black pepper, long pepper)
- Polygodial (Dorrigo pepper)
- Probenecid
- Protons
- RhTx
- Rutamarin (Ruta graveolens)
- Resiniferatoxin (RTX) (Euphorbia resinifera/pooissonii)
- Shogaols (ginger, Sichuan and melegueta peppers)
- Tetrahydrocannabivarin (cannabis)
- Thymol (thyme, oregano)
- Tinyatoxin (Euphorbia resinifera/pooissonii)
- Tramadol
- Vanillin (vanilla)
- Zucapsaicin
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 | Original source: https://en.wikipedia.org/wiki/Dicentrine. Read more |
-(%2B)-dicentrine.svg)
