Über neue Basen des Tabaks (XIII. Mitteil. über Tabak‐Alkaloide)

Abstract

Bpath, Kesztler: [Jahrg. 70 auf dem Wasserbade vollendet, das abgeschiedene Wasser durch Evakuierung bei SOo vertrieben, bis das Gewicht nicht weiter abnahrn. Eine kleine Probe der Verbindung I1 ging bei 190° (Luftbad) und 0.03 mm als farblose olige Fliissigkeit iiber. 3.037 mg Sbst. : 5.41 ccm n/Die Hauptirienge wurde mit 3.3 g J o d m e t h y l eingeschmolzen, 16 Stdn. bei ZOO belassen und dann 9 Stdn. auf 60-700 erhitzt. Das zahfliissige, gelbrote Resktionsprodukt, das die Verbindung I11 vorstellte, wurde in 40 ccm Methylalkohol gelost, 5 ccm Wasser zugesetzt und 15 Min. unter RiickfluB gekocht. Dann wurden im offnen Becherglas 100 ccm heiBes l) B. 68, 1667 [1935]. E, B. 70, 704 [1937].

Efficient Enantiomeric Synthesis of Pyrrolidine and Piperidine Alkaloids from Tobacco

“…The optical rotation of our synthetic ( S )- N -methylanatabine 4 ([α] 20 D −157.5 ( c 0.8, MeOH)) and ( S )- N -methylanabasine 6 ([α] 20 D −132.3 ( c 0.8, MeOH)) matched those reported by Spath for the natural products, [α] 20 D −171.4 (c 0.5, MeOH) and [α] 20 D −143.8 (c 0.4, MeOH) for ( S )- N -methylanatabine 4 and ( S )- N -methylanabasine 6 respectively.…”

Pyridine alkaloids with activity in the central nervous system

“…5 ), was isolated from the leaves of N. tabacum by Spath and Kesztler in 1937; 53 its chemical structure was affirmed through total synthesis in the same study. 53 Although structurally similar to nicotine and anatabine, studies on the biological activities of N -methylanatabine are scarce in the current literature database. The interactions of N -methylanatabine and monoamine oxidase (MAO) A and B were evaluated by Castagnoli and co-workers; 54 the group established that N -methylanatabine did not produce any significant changes of MAO-A and B activities in rat brain upon administration (data not shown).…”

“…An N -methylated anatabine isomer, N -methylanatabine ( Fig. 5 ), was isolated from the leaves of N. tabacum by Spath and Kesztler in 1937; 53 its chemical structure was affirmed through total synthesis in the same study. 53 Although structurally similar to nicotine and anatabine, studies on the biological activities of N -methylanatabine are scarce in the current literature database.…”

The Chemical Constituents Of Tobacco And Tobacco Smoke

“…Nicotoin, which was not amply described, has never been found again, and isonicotein proved to be identical with 2,3'dipyridyl (314,321). Further alkaloids separated in earlier work include nornicotine (320), anabasine (316) [the chief alkaloid of N. glauca (309)], nicotyrine (317), N-methylanabasine (317), and N-methylanatabine (317), whilst several simpler bases isolated were ammonia (321), trimethylamine (321), pyrrolidine (243), N-methylpyrrolidine (314), N-methylpyrroline (37), piperidine (321), and traces of pyridine (20). A recent paper chromatographic investigation of the volatile bases of N. tabacum and N. rustica showed the presence of ammonia, methylamine, and isoamylamine, but not trimethylamine, in fresh leaves (331).…”