1 -Hydroxymethyl-1,2,3,4-tetrahydro-/!-carboline

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]...

Hydroxymethyl tetrahydro beta carboline formed from serotonin... 

Non-oxidative conversion of a tetrahydro-)8-carboline into a 3,4-dihydro derivative has also been described. Dehydration of 1-hydroxymethyl-1,2,3,4-tetrahydro-j8-carboline (146) yielded 1-methyl-3,4-dihydro-j8-carboline (135). Harmaline and l-methyl-3,4-dihydro-j8-carboline-3-carboxylic acid were obtained in an analogous manner. ... 

Mannich reaction, and this method has recently been extended and repeatedly applied (see Section IV, B, 2). It involves treating a 1-m-hydroxybenzyl-1,2,3,4-tetrahydro-jS-carboline derivative (389) with formaldehyde at pH 4.4. When the aqueous solution of the hydrochloride of the hydroxymethyl derivative so formed is made basic with sodium carbonate, the pentacyclic base (390) precipitates. 

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