Methoxy tryptamine

Julia, M., and Manoury, P. (1965) Research in the indole series. XIII. 5- and 6-Methoxy-tryptamines. Bull. Soc. Chim. Fr., 1411-1417. 

Illustrated for 5-methoxy-tryptamine (1). 1.5 g (1), 30 ml ethanol add 5 g methyl iodide (or equimoiar amount ethyl iodide) and 4.5 g dry sodium carbonate and heat five hours on water bath. Filter hot, heat precipitate with ethanol and filter hot again. Evaporate in vacuum to get 2.5 g l-methyl-5-methoxy-DMT. 

Dissolve 1 g OH-tryptamine in methanol or ether add 2.5 g diazomethane in ether and heat twenty hours. Evaporate in vacuum to get the methoxy-tryptamine. 

Dissolve 4 g glyoxylic acid monohydrate in 220 ml water and add with stirring to a solution of 10 g 4,5, or 6 methoxy-tryptamine-HCl in 80 ml water. Adjust pH to 4 with 10% KOH and stir five hours at room temperature. Filter and wash with water to get about 4.5 g precipitate. Melt to decarboxylate or to 4 g precipitate add 30 ml concentrated HCI and 100 ml water and heat at 65° one hour. Add water to dissolve the solid and add excess 10% KOH. Filter to get the title compound or analog. 

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... 

SYNS 3-(2-AMINOETHYL)-l-BENZYL-5-METHOXY-2-METHYLINDOLE HYDROCHLORIDE BAS BENANSERIN HYDROCHLORIDE BENZYL ANTISEROTONIN l-BENZYL-2-METHYL-3-(2-AiMINOETHYL)-5-METHOXYINDOLE HYDROCHLORIDE 1-BENZYL-2-METHYL-5-METHOXY-TRYPTAMINE HYDROCHLORIDE SEROTONIN BENZYL ANALOG WOOLLEY S ANTISEROTONIN... 

Of much interest is the recent discovery of substances closely related to the harmala alkaloids in animals. One of these is adrenoglomerulotropine, a hormone of the pineal body, the chemical identity of which has been indicated as 2,3,4,9-tetrahydro-6-methoxy-i-methyl-iH-pyrido (3,4,6) indole. This substance is identical to 6-methoxyletrahydroharman which has been shown to be formed in vivo from 5-methoxy tryptamine and acetaldehyde. 6-methoxytetrahydroharman is an isomer of tetrahydro-harmine, one of the alkaloids in Banisteriopsis, and in the African Leptactinia densillora. One more substance, 6-methoxyharmalan, has been shown to derive, at least in vitro, from melatonin, which results from the methylation of acetylserotonin. The enzyme which makes this possible, hydroxyindole O-methyl transferase, has only been found in the pineal body. (Naranjo, in Efron et al. 

Other workers [64] utilized the NICI mode for studying melatonin (iV-acetyl methoxy tryptamine) derivatized with pentafluoropropionic anhydride and showed that this method had a great sensitivity. 

A model (95) for structure A has been obtained by condensation of 6-methoxy-tryptamine with dihydrocorynantheal. The mass spectrum of this compound is significantly different from those of the dihydro-derivatives of (91) and (92), although on the other hand the same is true of the mass spectra of (91) and (92) themselves. However, structure B for cinchophyllamine (91) and isocincho-phyllamine (92), thought to be C(3)-epimers, is preferred to structure A. 

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... 

HTg receptors have been identified mainly using the pharmacological criteria defined by Bradley et al. [73] 1) They should be resistant to blockade by antagonists at 5-HT,-like, 5-HTg (and S-HTJ receptors 2) they should be responsive to PBG and 2-methyl-5-HT (but unresponsive to 5-methoxy-tryptamine) 3) they should be blocked by low concentrations of bemesetron, tropisetron (and the other specific 5-HTg antagonists, mainly zacopride and granisetron). Thus, 5-HTg receptors were found exclusively on neuronal membranes in the periphery and CNS. 

L-Tryptophan derivatives Serotonin, 5-methoxy-tryptamine (D 21.1) Vertebrates and invertebrates... 

The many hallucinogenic indole alkaloids, for instance, are related to serotonin and 5-methoxy-tryptamine,... 

Hydroxytryptamine is deaminated oxidatively to 5-hydroxyindole acetic acid. In addition, 5-hydroxytryptamine is catabolized in substantially smaller amounts by reduction to the corresponding alcohol, 5-hydroxytryptophol, (1868-70) is excreted in the free form and combined as the glucuronide or sulphate. 7V-Methylation of 5-hydroxytryptamine gives iV-methylsero-tonin, which can be methylated further to 7V, -dimethylserotonin (= bufotenine). The iV-methylation is catalysed by a relatively unspecific iV-methyltransferase. By acetylation of 5-hydroxytryptamine 7V-acetyl-serotonin is produced, which is an intermediary product in the course of the melatonin synthesis (= 5-methoxy-AT-acetylserotonin). The production of 5-methoxytryptamine, which we were able to demonstrate in normal human blood and urine, seems to occur fairly easily by deacetylation of melatonin, whereas a direct 0-methylation of serotonin to 5-methoxy-tryptamine, at least in vitro, takes place to a substantially smaller extent. ... 

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