477-57-6

Basic information

• Product Name: ISOTETRANDRINE
• Synonyms: 1-isotetrandrine;6,6’,7,12-tetramethoxy-2,2’-dimethyl-berbama;isosinomenina;isosinomeninea;o,o’-dimethylobamegine;o,o’-dimethylstepholine;O-METHYLBERBAMINE;BERBAMINE METHYL ETHER
• CAS NO: 477-57-6
• Molecular Formula: C₃₈H₄₂N₂O₆
• Molecular Weight: 622.75
• Product Categories: Alkaloids
• Mol File: 477-57-6.mol
• Article Data: 7

Chemical Properties

• Melting Point: 180-182℃
• Boiling Point: 710.5°Cat760mmHg
• Flash Point: 175.8°C
• Appearance: /
• Density: 1.172
• Vapor Pressure: 4.88E-20mmHg at 25°C
• Refractive Index: 1.585
• PKA: 7.70±0.20(Predicted)
• CAS DataBase Reference: ISOTETRANDRINE(CAS DataBase Reference)
• NIST Chemistry Reference: ISOTETRANDRINE(477-57-6)
• EPA Substance Registry System: ISOTETRANDRINE(477-57-6)

Safety Data

• RTECS: NX7285000
• Hazardous Substances Data: 477-57-6(Hazardous Substances Data)

Usage

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 inhibitor of G protein activation of PLA2.

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)

InChI:InChI=1/C38H42N2O6/c1-39-15-13-25-20-32(42-4)34-22-28(25)29(39)17-23-7-10-27(11-8-23)45-33-19-24(9-12-31(33)41-3)18-30-36-26(14-16-40(30)2)21-35(43-5)37(44-6)38(36)46-34/h7-12,19-22,29-30H,13-18H2,1-6H3/t29-,30+/m1/s1

Upstream product

• 186581-53-3 diazomethane 
• 38769-07-2 fangchinoline 
• 436-77-1 demethyltetrandrine 
• 66277-16-5 didehydro-N-methylcoclaurinium iodide 
• 17934-80-4 (+/-)-1-(4-hydroxybenzyl)-7-hydroxy-6-methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride 
• 1472-62-4 N-methylcoclaurine 
• 67-56-1 methanol 
• 2973-76-4 5-bromo-4-hydroxy-3-methoxybenzaldehyde 
• 38849-59-1 5-(8-bromo-6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydro-isoquinolin-1-ylmethyl)-2-methoxy-phenol 
• 1131-94-8 homoisovanillic acid 
• 56139-04-9 2-(3-bromo-4,5-dimethoxyphenyl)ethanamine 
• 54291-90-6 5-bromo-3,4-dimethoxy-1-(2-nitrovinyl)benzene 
• 6948-30-7 5-bromoveratralaldehyde 
• 22231-61-4 2-[4-(benzyloxy)-3-methoxyphenyl]ethylamine 

Downstream Products

• 477-57-6 tetrandrine 
• 3423-05-0 (R)-7-methoxy-1-(4-methoxy-benzyl)-2-methyl-1,2,3,4-tetrahydro-isoquinolin-6-ol 
• 3423-07-2 (S)-N-methylcoclaurine 
• 5701-00-8 (R)-O-methylarmepavine 
• 5096-70-8 (-)-(R)-(N)-methylcoclaurine 
• 2107-55-3 (R)-6-ethoxy-7-methoxy-1-(4-methoxy-benzyl)-2-methyl-1,2,3,4-tetrahydro-isoquinoline 
• 115439-17-3 pycmanilline 
• 58169-28-1 secophaeanthine 
• 479-37-8 (+)-obamegine 
• 436-77-1 demethyltetrandrine 

Relevant articles and documents

Full-synthetic method of racemic tetrandrine

The invention discloses a full-synthetic method of racemic tetrandrine, and belongs to the technical field of drug synthesis. The full-synthetic method of the racemic tetrandrine comprises the steps that a synthetic route adopts a convergence synthesis method, a 5-bromovanillin, namely a compound 1 and 3-hydroxy-4-methoxyphenylacetic acid, namely a compound 5 are taken as starting materials to obtain a compound 4 and a compound 6 respectively, then the compound 4 and the compound 6 are taken as raw materials to synthesize a compound 11, a compound 19 is synthesized from the compound 11, and finally, the compound 11 reacts with the compound 19. The full-synthetic method of the racemic tetrandrine has the advantages that the synthetic efficiency is higher, the yield is higher, and the cost is lower; the reaction conditions are milder, the operation is simple and convenient, the industrial value is higher, and a reference is provided for the full-synthetic method of optical voidness tetrandrine.

Alcaloides bisbenzylisoquinoleiques de Albertisia cf. A. papuana

Four new bisbenzylisoquinoline alkaloids were obtained from Albertisia cf.A. papuana Becc. (Menispermaceae).These are (-)-2,2'-bisnorphaeanthine (5), (+)-pangkoramine (7), (+)-pangkorimine (9), and (+)-2'-norcocsuline (14).They are accompanied by the known (+)-daphnoline (2), which is the main alkaloid, and by seven known dimers with one, two, or three ether bridges

New alkaloids and related artifacts from Cyclea peltata

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