Do trypatmines have a habit of forming tar when compared to phenethylamines?
Yes, most definitely. Purification through flash chromatography (or short-path high-vac distillation) very often has to be performed to get something which can be crystallized as a salt.
Oh, and lastly does anyone here have first hand experience of the activity of the desired product?
Yes, such descriptions can be read in None (http://www.erowid.org/library/books_online/tihkal/tihkal11.shtml)
(http://www.erowid.org/library/books_online/tihkal/tihkal11.shtml)
In this paper, they reduce indolyl-nitroalkanes with nickel boride/hydrazine hydrate, rather than Pd/C.
And they prepare their intermediate nitro compound via a method similar to the one Starlight used - but deprotonate the nitroalkane beforehand, and thus get the indolylnitroalkane directly without having to reduce anything with NaBH4...
(https://www.thevespiary.org/rhodium/Rhodium/hive/hiveboard/picproxie_imgs/pdf.gif)
(abstract and title are mentioned here: Post 448477 (https://www.thevespiary.org/talk/index.php?topic=12835.msg44847700#msg44847700)
(hest: "AMT in the MW oven", Tryptamine Chemistry))
indole_amine