573-73-9

Basic information

• Product Name: magnolamine
• Synonyms: magnolamine;(1S)-1,2,3,4-Tetrahydro-1-[[4-[4-hydroxy-5-methoxy-2-[[(1S)-1,2,3,4-tetrahydro-7-hydroxy-6-methoxy-2-methylisoquinolin-1-yl]methyl]phenoxy]phenyl]methyl]-6-methoxy-2-methylisoquinolin-7-ol
• CAS NO: 573-73-9
• Molecular Formula: C36H40N2O7
• Molecular Weight: 626.74
• Mol File: 573-73-9.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: magnolamine(CAS DataBase Reference)
• NIST Chemistry Reference: magnolamine(573-73-9)
• EPA Substance Registry System: magnolamine(573-73-9)

Safety Data

• Hazardous Substances Data: 573-73-9(Hazardous Substances Data)

Usage

Description

This bisbenzylisoquinoline alkaloid is found in the benzene-soluble portion of the total alkaloids extracted from Magnolia fuscata. When recrystallized from C6H6 it yields fine, colourless needles, soluble in alkalies, CHC13 and EtOH. It is dextrorotatory with [α]D + 111.6° and yields a crystalline picrate, m.p. 142- SoC (dec.); a picrolonate, m.p. 163-4°C and a tetramethyl ether, m.p. lSI-2°C. The latter may be oxidized by KMn04 in Me2CO to give 1-keto-6:7-dimethoxy- 2-methyltetrahydroisoquinoline, m.p. 124-5°C and magnolaminic acid, C16H1407, m.p. 280-loC. The alkaloid acts as a cardiac depressant at between 10 to 500 parts per million.

References

Proskurnina, Orekhov., Bull. Soc. Chim., 5, 1357 (1938) Proskurnina., J. Gen. Chem. USSR., 16, 129 (1946) Tomita.,J. Pharm. Soc., Japan, 1075 (1951) Tomita, Kugo., Chem. Abstr., SO, 1056 (1956) Pharmacology: Buchi., Schweiz. Apoth. Zeit., 83, 198 (1945)

Upstream product

• 80248-83-5 tribenzylmagnolamine 
• 80248-85-7 L-(+)-6'-bromo-O,O-dibenzylreticuline 
• 19777-92-5 (S)-7-Benzyloxy-1-(5-benzyloxy-2-bromo-4-methoxy-benzyl)-6-methoxy-1,2,3,4-tetrahydro-isoquinoline 
• 17958-52-0 (S)-1-(4-hydroxybenzyl)-2-methyl-6-methoxy-7-benzyloxy-1,2,3,4-tetrahydro-isoquinoline 

Relevant articles and documents

ALKALOIDS OF MICHELIA FUSCATA BLUME: THE STRUCTURE AND SYNTHESIS OF MAGNOLAMINE

The cleavage reaction of triethylmagnolamine (3) by sodium-liquid ammonia determined the location of phenolic functions in magnolamine (2).Furthermore, the synthesis of magnolamine was carried out by the Ullmann reaction of two optically active compounds (10) and (12).The synthetic product was completely identical with natural magnolamine by comparison of various spectra and t.l.c. behavior.Thus, it was clarified that the structure of magnolamine is indicated by the formula (2).