From Wikipedia, the free encyclopedia
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
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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).
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Chemical compound
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
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^ 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.
- ^
a
b 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.
Bibcode:
2013PLoSO...867730M.
doi:
10.1371/journal.pone.0067730.
ISSN
1932-6203.
PMC
3701576.
PMID
23861794.
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TRPA | Activators |
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4-Hydroxynonenal
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4-Oxo-2-nonenal
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4,5-EET
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12S-HpETE
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15-Deoxy-Δ12,14-prostaglandin J2
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α-Sanshool (
ginger,
Sichuan and
melegueta peppers)
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Acrolein
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Allicin (
garlic)
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Allyl isothiocyanate (
mustard,
radish,
horseradish,
wasabi)
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AM404
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ASP-7663
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Bradykinin
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Cannabichromene (
cannabis)
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Cannabidiol (
cannabis)
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Cannabigerol (
cannabis)
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Cinnamaldehyde (
cinnamon)
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CR gas (dibenzoxazepine; DBO)
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CS gas (2-chlorobenzal malononitrile)
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Cuminaldehyde (
cumin)
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Curcumin (
turmeric)
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Dehydroligustilide (
celery)
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Diallyl disulfide
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Dicentrine (
Lindera spp.)
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Farnesyl thiosalicylic acid
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Formalin
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Gingerols (
ginger)
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Hepoxilin A3
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Hepoxilin B3
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Hydrogen peroxide
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Icilin
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Isothiocyanate
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JT-010
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Ligustilide (
celery,
Angelica acutiloba)
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Linalool (
Sichuan pepper,
thyme)
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Methylglyoxal
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Methyl salicylate (
wintergreen)
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N-Methylmaleimide
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Nicotine (
tobacco)
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Oleocanthal (
olive oil)
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Paclitaxel (
Pacific yew)
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Paracetamol (acetaminophen)
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PF-4840154
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Phenacyl chloride
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Polygodial (
Dorrigo pepper)
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Shogaols (
ginger,
Sichuan and
melegueta peppers)
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Tear gases
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Tetrahydrocannabinol (
cannabis)
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Tetrahydrocannabiorcol
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Thiopropanal S-oxide (
onion)
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Umbellulone (Umbellularia californica)
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WIN 55,212-2
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Blockers | |
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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 |
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2-APB
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5',6'-EET
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9-HODE
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9-oxoODE
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12S-HETE
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12S-HpETE
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13-HODE
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13-oxoODE
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20-HETE
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α-Sanshool (
ginger,
Sichuan and
melegueta peppers)
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Allicin (
garlic)
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AM404
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Anandamide
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Bisandrographolide (
Andrographis paniculata)
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Camphor (
camphor laurel,
rosemary,
camphorweed,
African blue basil,
camphor basil)
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Cannabidiol (
cannabis)
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Cannabidivarin (
cannabis)
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Capsaicin (
chili pepper)
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Carvacrol (
oregano,
thyme,
pepperwort,
wild bergamot, others)
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DHEA
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Diacyl glycerol
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Dihydrocapsaicin (
chili pepper)
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Estradiol
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Eugenol (
basil,
clove)
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Evodiamine (
Euodia ruticarpa)
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Gingerols (
ginger)
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GSK1016790A
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Heat
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Hepoxilin A3
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Hepoxilin B3
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Homocapsaicin (
chili pepper)
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Homodihydrocapsaicin (
chili pepper)
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Incensole (
incense)
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Lysophosphatidic acid
- Low
pH (acidic conditions)
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Menthol (
mint)
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N-Arachidonoyl dopamine
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N-Oleoyldopamine
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N-Oleoylethanolamide
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Nonivamide (PAVA) (
PAVA spray)
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Nordihydrocapsaicin (
chili pepper)
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Paclitaxel (
Pacific yew)
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Paracetamol (acetaminophen)
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Phenylacetylrinvanil
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Phorbol esters (e.g.,
4α-PDD)
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Piperine (
black pepper,
long pepper)
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Polygodial (
Dorrigo pepper)
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Probenecid
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Protons
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RhTx
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Rutamarin (
Ruta graveolens)
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Resiniferatoxin (RTX) (
Euphorbia resinifera/
pooissonii)
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Shogaols (
ginger,
Sichuan and
melegueta peppers)
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Tetrahydrocannabivarin (
cannabis)
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Thymol (
thyme,
oregano)
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Tinyatoxin (
Euphorbia resinifera/
pooissonii)
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Tramadol
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Vanillin (
vanilla)
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Zucapsaicin
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Blockers | |
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