B-Carbolines

Tryptamine, with glyoxylic acid to give 1,2,3,4-tetrahydro-B-carboline, 51, 136... 

Biochemistry and pharmacology of tryptamine and B-carboline derivatives A minireview." Journal of Psychoactiv Drugs 16 (1984) 347-58. 

Dennis J. McKenna, G. H. N. Towers, and F. S. Abbott. "Mono-amine oxidase inhibitors in South American hallucinogenic plants Tryptamine and B-carboline constituents of Ayahuasca". Journal of Ethnopharmacology 10 (1984) 195-223. 

Crawley J, Ninan P, Pickar D Neuropharmacological antagonism of the B-carboline-induced anxiety response in rhesus monkeys. J Neurosci 5 455-485, 1995... 

The principal reason that DMT must be administer parenterally is its rapid and efficient metabolism. It can be oxidized to the N-oxide. It can be cyclized to b-carbolines, both with and without an N-methyl group. It can be N-dealkylated to form NMT and simple tryptamine itself. Best known is its oxidative destruction, by the monoamine oxidase system, to the inactive indoleacetic acid. There is a wild biochemical conversion process known for tryptophan that involves an enzymatic conversion to kynurenine by the removal of the indole-2-carbon. A similar product, N,N-dimethylkynuramine or DMK, has been seen with DMT, when it was added to whole human blood in vitro. 

HARMAN, 6-METHOXY-1,2,3,4-TETRAHYDRO b-CARBOLINE, 6-METHOXY-1 -METHYL-1, 2,3,4-TETRAHYDRO 6-METHOXY-1,2,3,4-TETRAHYDROHARMAN 10-METHOXY-3,4,5,6-TETRAHYDROHARMAN 6-METHOXY-1 -METHYL-1,2,3,4-TETRAHYDRO-b-CARBOLINE 1-METHYLPINOLINE ADRENOGLOMERULOTROPIN ALDOSTERONE-STIMULATING HORMONE MCISAAC S COMPOUND... 

Methoxy-tetrahydroharman (6-MeO-THH) is the title chemical of this recipe. This particular b-carboline is a focal points of an ongoing controversy. To put all the cards directly on the table, this compound can in theory be made easily in the body and thus it could be present as a normal component in the brain. It has been synthesized by Mclsaac, in Texas, under physiological conditions, with acetaldehyde and 5-methoxytryptamine. And, so the reasoning goes, if it can be made under these conditions in the laboratory, why not in the brain He was completely convinced that it would be found some day to play an important role in mental health, just as he was convinced that it would prove to be a psychoactive compound. Perhaps it would be the product of some psychological trauma, or maybe be the source of such a trauma. He once told me (at a meeting years ago, over a quiet breakfast) that one of his ambitions was to assay the brains of people who were in all different kinds of mental states at the time of their deaths, and to correlate the carboline levels with that mental state. I asked him if he had personally tasted the material, and apparently he had not. 

One of the most valuable and widely used applications of C=N bond hydrogenation is in the field of reductive alkylation, in which an aldehyde or ketone is condensed with an amine and reduced in situ with an appropriate catalyst to give a substituted product. This very valuable reaction has most notably been employed for the racemic synthesis of amino acids from a-ketoesters and acids. This type of reduction can be very powerful, as illustrated by the synthesis of tetrahydro-b-carbolines 64 (76% yield) by the reductive coupling of 65 and 66 under conditions of 1 atm of hydrogen and palladium on carbon catalyst277. 

N. Ide, M. Ichikawa, K. Ryu, K. Ogasawara, J. Yoshida, S. Yoshida, T. Sasaoka, S.-I. Sumi, and H. Sumiyoshi, Antioxidants in processed garlic. II. Tetrahydro-b-carboline derivatives identified in aged garlic extract, in G, 2002, 449 150. 

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