| Identification | Back Directory | [Name]
ISOTETRANDRINE | [CAS]
477-57-6 | [Synonyms]
NSC 97338
isosinomenina
isosinomeninea
ISOTETRANDRINE
1-isotetrandrine
O-METHYLBERBAMINE
(r,s)-tetrandrine
BERBAMINE METHYL ETHER
o,o’-dimethylobamegine
o,o’-dimethylstepholine
6,6’,7,12-tetramethoxy-2,2’-dimethyl-berbama
(4aS,16aR)-3,4,4a,5,16a,17,18,19-Octahydro-12,21,22,26-tetramethoxy-4,17-dimethyl-16H-1,24:6,9-dietheno-11,15-metheno-2H-pyrido[2',3':17,18][1,11]dioxacycloeicosino[2,3,4-ij]isoquinoline
16H-1,24:6,9-Dietheno-11,15-metheno-2H-pyrido[2',3':17,18][1,11]dioxacycloeicosino[2,3,4-ij]isoquinoline, 3,4,4a,5,16a,17,18,19-octahydro-12,21,22,26-tetramethoxy-4,17-dimethyl-, (4aS,16aR)- | [Molecular Formula]
C38H42N2O6 | [MDL Number]
MFCD00236404 | [MOL File]
477-57-6.mol | [Molecular Weight]
622.75 |
| Chemical Properties | Back Directory | [Melting point ]
180-182℃ | [Boiling point ]
710.5±60.0 °C(Predicted) | [density ]
1.172 | [RTECS ]
NX7285000 | [solubility ]
Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | [form ]
Off-white solid. | [pka]
7.70±0.20(Predicted) | [color ]
White to light yellow | [InChIKey]
WVTKBKWTSCPRNU-PKGWHCLJNA-N | [SMILES]
O(C1C(=CC2CCN(C)[C@]3([H])CC4=CC=C(OC)C(OC5C=CC(=CC=5)C[C@]5([H])N(C)CCC6C=C(OC)C(=CC=65)OC=1C3=2)=C4)OC)C |&1:9,27,r| |
| Hazard Information | Back Directory | [Description]
A bisbenzylisoquinoline alkaloid, shown to be identical with berbamine methyl
ether, this base occurs in A therosperrna rnoschaturn, Berberis japonica and
Stephania cephalantha. It is dextrorotatory with [α]17D + 146° or[α]20D +
150.7° (c 0.85, CHC13). When recrystallized from MeOH it forms colourless
crystals and furnishes a crystalline dimethiodide, m.p. 242°C. Four methoxyl
groups and two methylimino groups are present. | [Uses]
Isotetrandrine is a biscoclaurine alkaloid which inhibits G-protein mediated activation of phospholipase A2 (PLA2) but not phospholipase C (PLC) or D (PLD). Cell permeable. | [target]
IL Receptor | NF-kB | MAPK | Nrf2 | HO-1 | JNK | [References]
Kondo et al., J. Pharrn. Soc., Japan, 58,920 (1938)
Tomita, Fujita, Morai., ibid, 71,226,301 (1951)
Bick, Clezy, Crow., Austral. J. Chern., 9, III (1956)
Synthesis:
Inubushi et ai., Tetrahedron Lett., 3399 (1968)
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