Beta-carbolines structure

Mclsaac, W., Estevez, V. Structure-action relationship of beta-carbolines as monoamine oxidase inhibitors. Biochem. Pharmacol. 15 1625, 1966. 

Structures 23, 24. Harman (82) and norharman (83) have been isolated from cigarette smoke (175), and Janiger and deRios (122) have suggested that some of the tobacco-induced altered states reported by South American Indians might be related to the cumulative effects of these beta-carbolines. 

Compounds such as LSD or the beta-carbolines do not possess a primary amino group, are not rapidly metabolized in comparison to, for example, tryptamine, and enter the brain readily certain substituent groups can alter this situation. Members of the phenylalkylamine and indolealkylamine families of hallucinogens can produce similar effects in animals but may be capable of producing distinctive effects in man. As yet, there is no satisfactory and comprehensive structure-activity relationship that encompasses both major classes of compounds. This may be due in part to unique metabolic and distributional characteristics associated with the individual ring systems. 

Figure 1. Structures of representative phototoxic plant products from various phytochemical classes. (I) 1-phenylhepta-1,2,3-triyne (acetylenic polyine) (II) 6-methoxyeuparin (benzofuran) (III) harmane (beta-carboline alkaloid) (IV) khellin (furo-chromone) (V) 8-methoxypsoralen (furocoumarin) (VI) dictamnine (furoqulnoline alkaloid) (VII) nordihydroguaiaretic acid (lignan) and (VIII) alpha-terthienyl (thiophene).

Albores, R., Neafsey, E.J., Drucker, G Fields, J.Z. and Collins, M.A. (1990) Mitochondrial respiratory inhibition by Al-methylated beta-carboline derivatives structurally resembling Al-methyI-4-phenylpyridine. Proc. Natl. Acad. Sci. USA 87 9368-9372. 

Fig. 19.1 Structure of some P-carbolines synthesized biologically and chemically (1) Prom plant (a, b, c, d, e, f, and g) (2) Prom animals (a, d, g,h, i, j, and k) (3) Synthesized chanically (1 and m). (a) Harman (b) harmaline (c) harmine (d) norharman (e) hatmol (f) harmalol (g) tetrahydrohatmine (h) tryptoline (i) pinoline (j) l-(2-guanidinoethyl)-l,2,3,4-tetrahydro-6-hydroxymethyl)-P-carboline [37] (k) manzamine A [39] (1) 3-ethyl-l-phenyM,9-dihydro-3//-beta-carbolme (m) lV-butyl-1-(4-dimethylammo)phenyl-l,2,3,4-tetrahydro-P-carboline-3-carboxamide [40]...

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