Short version: Can aqueous harmaloid bases be refluxed for an hour without being oxidized?

I was doing a VDS pH metric separation of 6 grams of harmine + harmaline as a trial run before scaling up. At the end I had chloride-free pH 9.70 waste water that was deep yellow that I dumped out, but I now somewhat regret that. Upon calculating yields of the three dried products I saw that I had a loss of 16% of the starting alkaloid mass, this is on par with the loss in manske precips.
In manske waste streams people have observed that basing wont get any meaningful portion out and, due to the solution being half saturated with salt, cooking it down is impractical. But in a pH metric separation there would be no problem there.
Since tryptamines and other indoles [including harmaloids?] tend to be destroyed by strong acids the ammoniacal solution could be neutralized with citric acid or similar prior to concentration, but most convenient would be if I could just distill the based solution down in my lab until most of the alkaloid base precipitated.
Has anyone attempted something similar to this?

So you suspect your alks are based, but don't all precipitate? Have you tried adding more ammonia to see if more crashes out?

I didn't know concentration was an issue with freebase precipitation. In my extractions I base like 10 liters of unreduced 200-300g rue tea and still get good yields (~5% post-Manske).

Also I don't know about harmalas being destroyed by strong acids. The DHH -> THH reduction can be done with HCl instead of vinegar. I've acidified my harmaline with HCl to pH 1.0 and still got yields similar to those at higher pH levels.

Well I didnt want to be wasteful of ammonia, it would take a significant quantity of ammonia to get substantially higher than the 9.70 I stopped at and even if adding NaOH it would require a fair bit to get past the buffering effect of ammonium acetate.
I get harmala seed for the 'cost' of harvesting and cleaning them myself whereas I have to pay for lye and ammonia [both of which are considered suspicious sales]. Add to that what I've seen in archives here of people loosing 10%+ per manske cycle and not recovering the loss by basing and simple distillation to reduce volume by 80% seems an attractive option, if viable. When given a choice of investing time or money/risk I usually choose time
I've been distilling solvents and reagents every few days lately so one extra distillation cycle would seem trivial.

I also never observed any oxidation. I was once lazy and converted harmine, DHH and THH bases to HCl salt by dumping conc. HCl over them and evaporating the water. Harmalas crystallized just fine and no oxidation products were observed.

The DHH -> THH conversion was compromised by excess air exposure though (strong overhead stirring for 24+ hours), forming some weird burgundy-colored side product and noticeable loss of yield.