Harmalane carbolines

To synthesize 6-methoxy-3,4-dihydro-beta-carboline (10-meth-oxy-harmalan), add 5-methoxy-tryptamine to acetic anhydride and let stand twelve hours at 10°. Dilute with water, basify and extract with methylene Cl and dry, evaporate in vacuum to get melatonin (I). Reflux (1) in xylene in the presence of P205 to get the title compounds. Other References JMC 7,136(1964) JPS 57,1364 (1968), 59,1446(1970) JACS 70,219(1948) JCS 1602(1921), 1203(1951), 4589,4593(1956) Organic Synthesis 51, 136... 

Since these molecules have been isolated and synthesized, a number of other p -carboline alkaloids have been developed in the laboratory. Michael Valentine Smith describes the preparation of several analogues in his Psychedelic Chemistry. The 6- or 10-methoxy isomer of harmaline, sometimes known as 10-methoxy-harmalan, is about half again as potent by weight as harmaline. 

To synthesize 6-methoxy-3,4-dihydro-beta-carboline (10-meth-oxy-harmalan), add 5-methoxy-tryptamine to acetic anhydride and let stand twelve hours at 10°. Dilute with water, basify and extract with methylene Cl and dry, evaporate in vacuum to get melatonin... 

The failure of AT-acetyltryptamine to act as a precursor for the tetrahydro- -carboline alkaloid eleagnine (54), in contrast to its successful incorporation into the j -carboline harman (53), has led to the suggestion that they may arise by different routes." This is supported by the successful isolation by radioisotope dilution of iV-acetyltryptamine from P. edulis, " but failure under similar conditions to detect it in E. angustifolia. In contrast, however, eleagnine (54) and harmalan (59) are efficiently and specifically incorporated into harman in P. 

Using this system of nomenclature the compounds which are most commonly encountered in the older literature and are there designated by trivial names are described as follows harmine = 7-methoxy-l-methyl-jS-carboline, harmol = 7-hydroxy-l-methyl-j3-carboline, harman= 1-methyl-j8-carboline, norharmine = 7-methoxy-)S-carboline, norharman = /3-carlx>-line, harmaUne = 7-methoxy-l-methyl-3,4-dihydro-j8-carboline, harmalol = 7-hy iroxy-l-methyl-3,4-dihydro-/5-carboline, and harmalan = 1-methyl-3,4-dihydro-j8-carboline. 

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