6-methoxytryptamine

Spath and Lederer have published a simplified synthesis of harmaline consisting in treating the acetyl derivative of 6-methoxytryptamine (XXIX) with phosphorus pentoxide in boiling xylene, the harmaline thus produced being converted into harmine by catalytic dehydrogenation at 200°. 

The polyamines putrescine, cadaverine, spermidine, and spermine, which are seen at elevated levels in some victims of cancer, were separated on a Technicon (The Technicon Company Chauncey, NY) TSM Amino Acid Analyzer packed with an 8% divinylbenzene-co-polystyrene sulfonated resin with post-column ninhydrin detection.111 Amines such as ethanolamine, noradrenaline, hexamethylene diamine, methoxytryptamine, spermine, and spermidine were separated from amino acids on a DC-4A cation exchange resin.112 A similar approach, using a Beckman Model 121M amino acid analyzer equipped with an AA-20 column, was also successful.113 A Polyamin-pak strong cation exchange column (JASCO) was eluted with a citrate buffer for the detection of putrescene, spermine, cadaverine, and 1,5-diaminohex-ane from rat thymus.114 A post-column o-phthaldehyde detection system was used. 

DeMontigny, C., and Aghajanian, G. K. (1977) Preferential action of 5-methoxytryptamine and 5-methoxydimethyltryptamine on presynaptic serotonin receptors A comparative ion-tophoretic study with LSD and serotonin. Neuropharmacology, 16 811-818. 

Heinze, W. J., Schlemmer, R. F., Williams, J., and Davis, J. M. (1980) The acute and chronic effect of 5-methoxytryptamine on selected members of a primate social colony. Biol. Psychiatry, 15 829-839. 

Vogel, W. H. (1969) Physiological disposition of 5-methoxytryptamine and the rope climbing performance of rats. Psychopharmacologia, 15 88-95. 

Martin and co-workers (142,143) have found that, in animals, tryptamine produced many of the physiologic effects characteristic of LSD however, it does not appear to elicit behavioral effects similar to those of LSD. At relatively high doses, 5-methoxytryptamine (24) does produce some behavioral effects in rats (66,242) and in nonhuman primates (101). Vogel (242) has suggested that the disruptive effects of 5-methoxytryptamine might be due to the peripheral actions of this agent. Tryptamine had no effect on acquisition of avoidance behavior, whereas 5-methoxytryptamine slightly decreased such behavior (240). Both tryptamine and 5-methoxytryptamine produced discriminative effects in rats... 

Tryptamines that are unsubstituted on the terminal amine are good substrates for oxidative deamination by MAO. Furthermore, it has been demonstrated that tryptamine and 5-methoxytryptamine cross the blood-brain barrier with great difficulty administration of 50 mg/kg 5-methoxytryptamine to rats results in a low brain/plasma ratio when measured 15 min postadministration (242). 

In general, in animal research, it is well to be cautious, whether bufotenin or 5-methoxylated tryptamines or other substances postulated to be useful hallucinogenic tools are used and to be aware of the status of knowledge of their effects in humans, let alone on a characteristic battery of effects in animals. In rat, for example, 5-methoxytryptamine (20 mg/kg) appeared to markedly increase 5-HT metabolism as judged by 5-HIAA, although interfering factors in measurement were not ruled out (29). 

Melatonin is A-acetyl-5-methoxytryptamine, a simple derivative of serotonin. It is a natural hormone secreted by the pineal gland in the brain during the hours of darkness. It is involved in controlling the body s day-night... 

HT4 CNS and myenteric neurons, smooth muscle Gs, t cAMP 5-Methoxytryptamine, renzapride, metoclopramide ... 

Melatonin is /V-acetyl-5-methoxytryptamine (Figure 16-2), a simple methoxylated and /V-acetylated product of serotonin found in the pineal gland. It is produced and released primarily at night and has long been suspected of playing a role in diurnal cycles of animals and the sleep-wake behavior of humans. 

Evodia rutaecarpa (Juss.) Berth Wu Zhu Yu (Evodia) (fruit) Alkyl methyl quinolone alkaloids, evodiamine, limonin, evocarpine, rutaecarpine, N-methyl anthranilic acid, evodol, hydroxyevodiamine, N-methylanthranflamide, N,N-dimethyl-5 -methoxytryptamine, dehydroevodiamine.32,33,237 Antiemetic, analgesic, lower blood pressure, antibacterial. 

TRYPTAMINE, N-ACETYL-5-METHOXY INDOLE, 3-(2-ACETAMIDOETHYL)-5-METHOXY SEROTONIN, N-ACETYL-O-METHYL ACETAMIDE, N-[2-(5-METHOXYINDOL-3-YL)ETHYL] N-ACETYL-5-METHOXYTRYPTAMINE 3-(2-ACETAMIDOETHYL)-5-METHOXYINDOLE N-ACETYL-O-METHYLSEROTONIN N-[2-(5-METHOXYINDOL-3-YL)ETHYL]ACETAMIDE REGULIN... 

To a well-stirred, warm suspension of 6.0 g LAH in 100 mL anhydrous dioxane, there was added a warm solution of 3.2 g of 5-methoxy-3-indolylglyoxylamide in 100 mL of anhydrous THF. The mixture was held at reflux for 38 h, cooled, and the excess hydride decomposed by the sequential addition of wet dioxane followed by 10 mL 5% aqueous NaOH. The resulting solids were removed by filtration, and extracted several times with boiling dioxane. The filtrate and washings were combined, dried over solid KOH, stripped of solvent under vacuum yielding an oily residue. This was dissolved in 80 mL warm benzene, decolorized with charcoal, and the filtered solution treated with an anhydrous solution of HCI in EtOH until it was acidic. The precipitate that formed weighed, after air drying, 1.1 g (29%) with mp 230-235 °C. This solid was recrystallized from EtOH, which provided the product 5-methoxytryptamine hydrochloride... 

To a solution of 0.2 g 5-methoxytryptamine in 4 mL of glacial HOAc there was added 2.0 mL acetic anhydride and heated at steam-bath temperature for 1 min. The volatiles were removed under vacuum and the residue was ground up under a mixture of and petroleum ether to yield 0.2 g (82%) of a white solid. This, after recrystallization from an ethanol / petroleum ether mixture, provided N-acetyl-5-methoxytryptamine (melatonin) as white crystalline solid with a mp 116-118 °C. MS (in m/z) 173 (100%) indolemethylene+ 160 (97%) parent ion 232 (28%). IR (in cm-1) 713, 794, 825, 925, 1042, 1101, 1177. 

SYNTHESIS (from 5-methoxytryptamine) A solution of 0.95 g of free-base 5-methoxytryptamine was dissolved in 10 mL warm I PA and, after returning to room temperature, treated first with 2.8 mL diisopropylethylamine followed by 1.2 mL bromoethane. After 3 days, TLC showed considerable starting material, so there was added an additional 2.8 g of the amine and 1.2 g of the bromide and the room-... 

---