I am in pursuit of the tastiest variety of harmaloids for oral administration of pharmahuasca.
My experience with rue is that it is absolutely revolting.
Harmala HCl salt is a big step up but still not very tasty.
The freebase tastes okay but I worry that it would be less effective than the salt.
I'd like to test the tastyness of different salts. What is a good method for converting between Harmala HCl and another form, for example Harmala Fumarate?
Does anyone have anything to say about differences in taste between these compounds?

As you can see alkaloids do not taste very good. They are pretty bitter in general. Going from salt to salt really won't make that much of a difference if any at all. This is the realm of pure compounds, they just don't taste good. You know what you can do though right? Dissolve the Harmala HCl some into some orange juice(which will spoil after a long duration of time so don't plan on storing it forever). Problem solved? I guess if your really gung-ho about it remaining a solid you could cut the harmalas with raw cane sugar(sugar will turn moldy over time) or put a drop of watermelon extract onto the powder(which would probably end up tasting rancid anyways).

To go from HCl to fumarate you'd want to freebase, filter, dissolve in water with an appropriate amount of fumaric acid(going by molecular weights/molar ratios). HCl is convenient because 'harmala' chlorides are insoluble in chloride saturated solutions so it will precipitate out. While the fumarate chances are, will have to be evaporated, unless one has a good amount sodium fumarate and the common ion effect for this salt works as well(not sure if it would?).

Making sodium fumarate may seem like a menial task but it's actually a weak acid strong base titration(so you'd want to use NaOH or KOH no gypsying around this with carbonate or lime...). The pKa's for fumaric acid are 3.0 and 4.5(second ionization). And after doing as accurate of a titration as possible, this technique probably doesn't even apply and would be 'costly' on the fumaric acid side. So evaporation is probably your friend here...

So essentially, don't dump harmala hcl or freebase directly onto your tongue, put it in juice, or spend a bunch of time trying different salts and probably coming to find they will never taste 'good' due to the nature of what they are.

What I do to dose is mix Harmala HCl and DMT Fumarate into a small cup of hot water with honey.
Perhaps there isn't any difference between the taste of salts because in solution there really is no notion of salt, just ions.
It's just that there is such a dramatic difference between the taste of freebase and salt that I am hopeful there could be a way to improve the flavor.
Perhaps a really dark hot chocolate would help disguise the bitter taste.

As it has been said, pure alkaloids will in general taste pretty bad. What about putting it in capsules (and poking a hole for better efficiency) or wrap it in a bit of toilet paper or smoking paper and swallowing? This way you dont taste it.

My favourite way to dose harmalas (I only have freebase) so far is to mix with a small amount of lemon or lime juice to dissolve, then on top of this I add maybe 50–75mL apple and raspberry juice. I down the harmala solution then chase with a few glugs of alkaloid-free juice to clear any taste. For me the taste really isn’t that bad at all when dosed that way.

Another quick tip– when drinking things that don’t taste great is to keep the volume down and throw the liquid to the back of your throat, rather than letting it get all over your tongue, you will taste barely anything.

Just make sure your upper lip is in the down position LOL. Hitting your teeth with glass hurts and could potentially break them.

I just use Harmalas in freebased form, ime they absorb just fine orally, can be smoked, can be used sublingually, and they don't taste hardly bitter at all compared to the Harmala salts. I've always used Harmala freebase for oral consumption and see no reason to use salts, the freebase absorbs fine.

I was planning to try buccal harmaline benzoate later tonight, but after reading this I'll give the freebase a shot first. The benzoate appears to be sparingly soluble in water at room temperature, which is annoying. I've had impressive results with DMT benzoate, however.

Do you use anything to enhance absorption? DMSO, olive oil, CO2 etc.?

Do you have a successful way of forming harmala benzoate?

I added harmaline freebase, water, and a slight excess of benzoic acid to a shot glass, then heated it to near boiling with gentle stirring. All of the solids dissolved, and the solution was clear with the characteristic yellow color of harmaline salt solutions. After cooling there were red conglomerations each about the size of the ballpoint on a pen. I tried redissolving, but the rocks stubbornly refused. I wound up shearing off the bottom of my shot glass with thermal shock before I could try anything else.

I recently watched a YouTube video (relating to a topic that can't be discussed here), and there was a serotonin-creatine complex involved. Maybe something similar is happening with benzoate and harmaline. I'd be curious to see if anyone else gets the same results. And do harmine and thh behave differently?

A word on safety - I'm a little concerned about people replicating the DMT benzoates, giving them to a friend who gives it to another friend who tries to smoke it. Sodium benzoate is very safe when ingested whole, in fact I saw a patent that claims FDA approval for a 5meo-dmt benzoate insufflation device. However, heat could transform any AH*benzoate to benzene. I might try hydrolyzing some olive oil to its free fatty acids and use that instead. No risk is better than no risk. Perhaps it is time to raid the kitchen 👀

And for DMT benzoate I dissolved freebase DMT and benzoic acid in separate pots of heptane, then mixed them. Instant white cloud, and when it settles the heptane actually decants off nicely, no filtration required.

A few of us have tried many solvent combinations to form harmala benzoate but your process sounds interesting if it is indeed forming harmala benzoate.