1.2- Dimethyl-6-methoxytryptamine

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. 

D. oreophila contain N,N-dimethyl-5-methoxytryptamine, 2-methyl-6-methoxy-l,2,3,4-tetrahydro-6-carboline, together with hordenine and kokusaginine, and the stem bark contains kokusaginine and three other furanoquinoline bases. The leaves of D. drupacea yielded N,N-dimethyl-5-methoxytryptamine again the stem bark contained only quinoline alkaloids. 

The second route begins with l,2-dimethyl-6-methoxytryptamine, which is condensed with diethylethoxymethylenemalonate to give 726. When this vinylogous urethane was heated with acetic anhydride acetic acid (3 2), the vinylogous amide 725 was obtained in 52% yield as a mixture of epimers. The corresponding intermediate in the synthesis of vindorosine (99) was prepared from 1,2-dimethyltryptamine in 65% yield (309). 

Galeffi, C. et al. 1983, W-Dimethyl-5-methoxytryptamine, a comporient of a dart poison of the Tianoamd Indians Journal cfNatural Products 46 j ) 586-587. 

Gross, H. and Franzen, Fr., Tryptamine, A, A-dimethyltryptamine, AT,iV-dimethyl-5-hydroxytryptamine and 5-methoxytryptamine in human blood and urine. Nature 206, 1052 (1965). 

Phalaris tuberosus.- This species, which contains W,iV-dimethyl-tryptamine and 5-methoxy-ff,ff-dimethyltryptamine as its main alkaloids, served as a source of two ff-methyltransferases which catalyzed the transfer of a methyl group from 5-adenosyl-L-methionine to tryptamine and 5-methoxytryptamine °. These enzymes also catalyzed the methylation of other indole-ethylamines... 

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