I would like to report that N-amyl acetate (pentyl acetate) is a workable solvent for liquid-liquid DMT extraction - and also for DMT benzoate recrystallization. It is fairly cheap at the online retailer.

One can extract DMT from alkaline water by shaking it vigorously with a few portions of amyl acetate. Unlike naphtha or heptane, it requires no heating. The combined extracts should be washed with small amounts of brine (concentrated NaCl in water) to absorb and remove most of the dissolved water and polar impurities.

One can then add excess benzoic acid pre-dissolved in a small amount of hot acetone (or amyl acetate) and stir for half an hour to protonate DMT into DMT benzoate, which precipitates as white powder.

Since DMT benzoate is somewhat soluble in room-temperature amyl acetate, it is ideal to chill or pre-evaporate the mixture. DMT benzoate crystals are collected, washed with cold acetone, and dried in air.

DMT benzoate can be recrystallized from hot amyl acetate (or, with a larger loss, from hot water). DMT benzoate is poorly soluble in acetone but very soluble in alcohols (ethanol, butanol).

Amyl acetate has a nice pear/banana smell. I bet isoamyl acetate, and other longer-chain or branched-chain acetates and benzoates, will also work as "green" extraction solvents.

Thanks for the info. As you may know, I've used butyl acetate a bit and that seems to be quite good to work with (banana flavour too). We can probably generalise about most of these lighter esters although I do wonder if their gradation of differences in properties might serve some useful purpose in some aspects of separation.