Indole Alkaloids of Acer saccharinum (the Silver Maple), Dictyoloma incanescens, Piptadenia colubrina, and Mimosa hostilis
Irwin J. Pachter, David E. Zacharias, Oscar Ribeiro
J. Org. Chem. 24, 1285-1287 (1959)
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_imgs/pdf.gif)
Abstract
Gramine was isolated from the leaves of Acer saccharinum L., N,N-dimethyl-5-methoxytryptamine from the bark of
Dictyobma incanescens D.C., bufotenine from the seeds of Piptadenia colubrina Benth., and N,N-dimethyltryptamine from the roots of Mimosa hostilis Benth.
Old and New Alkaloids from Zanthoxylum arborescens
Jonas A. Grina, Matthew R. Ratcliff, Frank R. Stermitz;
J. Org. Chem. 47, 2648-2651 (1982)
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_imgs/pdf.gif)
Abstract
The new alkaloids (2S,5S)-2,5-dibenzyl-1,4-dimethylpiperazine, 8-hydroxy-4,7-dimethoxyfuranoquinoline, and 8-isopentenyloxy-4,7-dimethoxyfuranoquinoline were isolated from Zanthoxylum arborescens (Rutaceae). The 6-D-glucopyranoside of hordenine (previously known only as a synthetic) was also found. The known alkaloids skimmianine, tembetarine, hordenine, N,”-dimethyltryptamine, N-methyltryptamine, l-methyl-3-(2’-phenylethyl)-1H,3H-quinazoline-2,4-dione and 1-methyl-3-[ 2’-(4’’-methoxyphenyl)ethyl]-1H,3H-quinazoline-2,4-dione also were isolated. Structure proof of the two new furanoquinoline alkaloids necessitated a revision in the previously suggested structure for perfamine, a cyclohexadienone alkaloid from Haplophyllum perforatum.
Swap the gramine with a cyanide ion, get the indoleacetonitrile.
And then Post 354293 (https://www.thevespiary.org/talk/index.php?topic=13167.msg35429300#msg35429300)
(Rhodium: "This together with what's been posted in Post ...", Tryptamine Chemistry) and Post 351772 (https://www.thevespiary.org/talk/index.php?topic=12580.msg35177200#msg35177200)
(Barium: "Nitriles to tertiary amines", Tryptamine Chemistry)
You will have DMT
Gramine can be used as a starting material for AMT and AET too, see https://www.thevespiary.org/rhodium/Rhodium/chemistry/it-290.html (https://www.thevespiary.org/rhodium/Rhodium/chemistry/it-290.html)