Methyl-corypalline

Nelumbium nelumbo Druce. Lian Zi Xin (Lotus) (plumule) Liensinine, isoliensinine, neferine, lotusine, methyl-corypalline, demethyl-coclaurine.33 Tranquilizing and antihypertensive. 

Methyl-corypalline Methyl eugenol Methyl isobutyl ketone Methyl isocupressate Methyl-l-propenyl disulfide Methyl-laurate Methyl-n-amyl ketone Methyl n-nonyl ketone Methyl nigakinone Methyl palmitate Methyl-pelletierine Methyl salicylate Methyl-swertianin Methylacetic acid Methylanthranilate Methylchavicol Methylcytisine... 

A new base, uberine, of structure (1), has been isolated from Dolichothele uberiformis O-Methyl-corypalline (2 R = Me) has been detected by mass spectrometry in Pilosocereus guerreronis, and corypalline (2 R = H) has been synthesized by Pictet-Spengler cyclization of N-methyI-/5-4-benzyloxy-3-methoxyphenyl-ethylamine, followed by debenzylation. A number of N-substi-tuted salsolidine derivatives (3), where R is PhCH2, PhS02, Me2CH, P-O2NC6H4,... 

Corypalline, CnHijOjN (Corydalis spp. Nos. 9, 22 list, p. 170). This phenolic base, m.p. 168°, picrate, m.p. 178°, contains one methoxyl group and on methylation yields 2-methyl-6 7-dimethoxytetrahydrof5oquinoline, Ci2Hi,02N, m.p. 82°, and on ethylation, 2-methyl-6-methoxy-7-ethoxy-tetrahydrofsoquinoline, m.p. 65°, whence the free hydroxyl appears to be at C and this has been confirmed by the synthesis of corypalline by a method analogous with that used by Spath, Orekhov and Kuffner. Corypalline is therefore hydrohydrastinine (XII) with the methylenedioxy group replaced by MeO at C and. OH at C (Manske). ... 

Corypalline (165 R = H)249 could be oxidatively dimerized electrochemi-cally in overall yields ranging from 44 to 85% depending on experimental conditions. Two types of dimers are obtained, the amount of carbon-carbon dimer 166 decreasing when R was varied from H through methyl to ethyl, and the product distribution shifted toward the carbon-oxygen-carbon dimer 167, presumably because of steric hindrance250 [Eq. (103)]. 

Isocorypal1ine (4, R =H, R =Me) has been oxidised by lead (IV) -acetate to the quinone acetal (5) which suffers Thiele acetylation to a product that may be hydrolysed and O-methylated to tehuanine (H. Hara et al.. Heterocycles, 1982, ]] (Special Issue), 293. Corypalline (4, R =Me, R =H) with lead tetra-... 

Lemaireocereine has been isolated from Backebegia militaris and a new quaternary alkaloid, pycnarrhine, identified as 7-hydroxy-6-methoxy-2-methyl-3,4-dihydroisoquinolinium chloride, has been isolated from Pycnarrhena longifoliaCorypalline (1 R = H) has been oxidised by lead tetra-acetate to the dienone (2), which reacts with veratrole and with corypalline in the presence of trifluoro-... 

On methylation it yields 2-methyl-6,7-dimethoxytetrahydroisoquinoline (m.p. 82°), and upon ethylation, 2-methyl-6-methoxy-7-ethoxytetrahydro-isoquinoline (m.p. 65°). The synthesis of corypalline was accomplished by a route parallel to that used by Spath, Orekhov, and Kuffner (39) in their synthesis of salsoline. 

C. poAlida (Thunb.) Pere. Corypalline (44) Capauridine (45) Capaurimine (45) Capaurine (45) Scoulerine (45) d-Tetrahydropalmatine (45) di-Tetrabydropalmatine (45) FSl, CttHwOgN, m.p. 171" (45), yields dl-tetrahydro-palmatine on methyls-tion Protopine (45)... 

Some simple isoquinoline alkaloids (carnegine, salsoline, corypalline, hydrohydrastinine) may be considered as bio-products of the interaction of hydroxytyramine and acetaldehyde or formaldehyde, followed by methylation. Actually, Schopf and Bayerle (93) obtained a surprisingly high yield of norcarnegine by carrying out this condensation under mild ( physiological ) conditions, that is, at pH 5 and 25°. 

Hydroxytetrahydroisoquinolines are methylated at C-8 by thiomethyla-tion followed by Raney nickel desulfurization. 8-Methylcorypalline was thus obtained from corypalline in high yield. ... 

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