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517-66-8

517-66-8 Structure

517-66-8 Structure
IdentificationBack Directory
[Name]

Dicentrin
[CAS]

517-66-8
[Synonyms]

Nsc406035
dicentrine
DICENTRINE95%
(S)-dicentrine
o,N-Dimethyllitseferine
1,2-Methylenedioxy-9,10-dimethoxyaporphine
9,10-Dimethoxy-1,2-(methylenedioxy)aporphine
1,2-(Methylenedioxy)-9,10-dimethoxy-6aalpha-aporphine
9,10-Dimethoxy-1,2-(methylenedioxy)-6aalpha-aporphine
6A.alpha.-Aporphine, 9,10-dimethoxy-1,2-(methylenedioxy)-
(7aS)-6,7,7a,8-Tetrahydro-10,11-dimethoxy-7-methyl-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline
5H-Benzo[G]-1,3-benzodioxolo[6,5,4-de]quinoline, 6,7,7A,8-tetrahydro-10,11-dimethoxy-7-methyl-, (S)-
5H-Benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline,6,7,7a,8-tetrahydro-10,11-dimethoxy-7-methyl-, (7aS)-
[Molecular Formula]

C20H21NO4
[MDL Number]

MFCD00210492
[MOL File]

517-66-8.mol
[Molecular Weight]

339.39
Chemical PropertiesBack Directory
[Melting point ]

177-178℃
[Boiling point ]

481℃
[density ]

1.266
[refractive index ]

1.6250 (estimate)
[Fp ]

143℃
[storage temp. ]

4°C, protect from light
[solubility ]

Soluble in DMSO
[form ]

Solid
[pka]

6.65±0.20(Predicted)
[color ]

Off-white to light brown
[InChI]

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
[InChIKey]

YJWBWQWUHVXPNC-AWEZNQCLSA-N
[SMILES]

N1(C)[C@]2([H])C3=C(C4=C(C=C3CC1)OCO4)C1=CC(OC)=C(OC)C=C1C2
Questions And AnswerBack Directory
[Description]

D-Dicentrine is an aporphinic alkaloid found in several plant species, mainly from family Lauraceae, including Lindera megaphylla. D-Dicentrine shows antinociceptive activity in a mouse model of pain. It probably acts via a TRPA1-dependent mechanism. D-Dicentrine is an alpha 1-adrenoceptor antagonist effective against human hyperplastic prostates.

[Anti-cancer Activity]

D-Dicentrine, a naturally occurring aporphine type isoquinoline alkaloid, isolated from the root of Lindera megaphylla Hemsl. (Lauraceae), was evaluated for its potential anti-cancer activity. Huang RL etc. found d-dicentrine significantly inhibited the growth of human hepatoma cell line HuH-7 by delaying its doubling time in tissue culture. An in vitro colony forming assay showed that d-dicentrine decreased the colony formation efficiency in both hepatoma cell lines, HuH-7 and MS-G2, used in our study.

Hazard InformationBack Directory
[Uses]

d-Dicentrine is a natural aporphine alkaloid extracted from the root of L. megaphylla which displays antitumor effects through inhibition of topoisomerase II.
[Definition]

ChEBI: Dicentrine is an aporphine alkaloid.
[IC 50]

α adrenergic receptor
[storage]

4°C, protect from light
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