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The Big & Dandy Syrian Rue & Harmala MAOI Alkaloids Thread

Most people seem to find huge differences between the subjective effects of MAOIs within the "harmaloid" class alone. Of harmaline, harmine, and tetrahydroharmine, harmaline is generally reported to be the least recreational, and the most sedating and "stoning" of the harmala alkaloids, but the most potent MAO inhibitor. THH is, on the other hand, reportedly stimulating, euphoric, and mildly psychedelic -- and the least effective MAOI. Harmine lies somewhere in the middle.

There's a wealth of information on MAOIs / RIMAs over at the DMT-Nexus.
 
Most people seem to find huge differences between the subjective effects of MAOIs within the "harmaloid" class alone. Of harmaline, harmine, and tetrahydroharmine, harmaline is generally reported to be the least recreational, and the most sedating and "stoning" of the harmala alkaloids, but the most potent MAO inhibitor.

Thanks! I think my first Ayahuasca experience might have been 100% the result of syrian rue. It was my first time taking an maoi and my first time taking mimosa. I assumed the insanely high body load was due to dmt, or mimosa. I assumed dmt was the main course, and Rue was just a little thing to make the dmt active. Then I learned both substances are active on their own, and syrian rue can be a monster all by itself. I don't think I metaolized any dmt bc I barfed up the mimosa within about 15 minutes, and only got a few sips. I took about 5g of Syrian Rue. I didn't see any characteristic dmt lines, but did become quite dreamy, and severely dizzy, which I suspect was the result of Rue. I shall experiment with mimosa and lower of syrian rue. I'd bet even 1.5g of Syrian Rue would be enough to activate dmt.
 
I know this post is 8 years old but I remember several of my freinds would get contact highs from the rest of us being on LSD. They would usually smoke a lot of hashish or high grade pot as well. In one case we wrote down what we believed was occurring without talking about it between 5 of us. After the experience a comparison of notes showed our experiences were not just similar but identical. A truely shared experience where we were not even sure whose mind was originating a thought.
 
I'd love to hear more experiences of the harmalas alone - I've search for many and it sounds potentially promising if more nausea inducing than somethings. Thinking of trying it as well as trying smoking either harmine or a harmaline/harmine mix.

As for moclobemide mention earlier in the thread by many it is totally different as a predose to mushrooms = in truth not a fan of shrooms but harmalas are far and away superior - they add there own spirit, they are the basis of ayahuasca (and sometimes used singularly which is why they deserve more attention).

Lotsof did some research into antiaddiction with these (somewhat closer to iboga than NN tryptamines) and of course Naranjo did therapuetic work - I feel they are like bufoteine a bit of an under researched molecule.

Finally are there any guesses to useful modifications or substitutions theorised for this substance/s? I'd be interested - in a minority I guess since everyone is so petrified of the MAOIs but it's actually reversable (RIMA); most of that is a bit over the top, not fully informed.
 
That is true but without testing there aren't many clues - I was wondering since some are well versed in chem/SAR if they had any intuitions or may if the chem has come any further - I guess not. I think at the DMT nexus or eslewhere one of the minor haramalas THH (?) had been isolated and got good results; must read it all again but it doesn't seem basic questions like moving the 5Me0 to the does or sticking on a 4OH would do; that might be over simplisic and a breif look again shows the number conventions don't look the same.

Post 153 tried harmaline/harmine before a small left over dose of LSD; no potentiation - some effects from the harmalas which did particularly help raise the small acid dose into anthing more useful. Were it a fairly useless amount of shrooms I am thinking a hefty harmala dose might have given some joy; the shrooms for their faults seems better meshed with it as well as potentially stronger.
 
Any clues on alternative routes of ingestion for harmalas?

Sprinkling some onto smokable herbs seems to work fairly well, and is pleasant.
Vaporizing it from a glass pipe is incredibly harsh on the lungs and you end up loosing a huge amount coughing.
Nasally it burns like hell.
 
Short and easy Question: How much Harmala Alkaloids can you extract from 100g of Syrian Rue ? In THIKAL it says ~ 4% Alkaloids, but as they don't say Harmine/Harmaline I thought it must be every Alkaloids and this is of course not the answer to my question then. Thx !
 
From experience harmaline didn't potentiate LSD - since it's active it can have additive effects though.
 
β-carbolines found in Peganum harmala, according to a recent review:

Harmaline

Harmine

Harmalol

Harmol

Harmane

Norharmane

Tetrahydroharmine

Tetrahydroharman

Harmalidine

Harmalacidine

1-Hydroxy-7-methoxy-β-carboline

Acetylnorharmine

Harmic acid methyl ester

Harmine N-oxide

Harmalanine

3-Hydroxylated harmine

2-Aldehyde-tetrahydroharmine

6-Methoxytetrahydro-1-norharmanone

8-Hydroxy-harmine

Dihydroharmane

Tetrahydroharmol

Harmalicine


This was filtered from the list in Table 4 in this article by Grok:

Peganum spp.: A Comprehensive Review on Bioactivities and Health-Enhancing. Sharifi-Rad, J., Quispe, C., Herrera-Bravo, J., Semwal, P., Painuli, S., Özçelik, B., Hacıhasanoğlu, F. E., Shaheen, S., Sen, S., Acharya, K., Amirian, M., Castillo, C. M. S., López, M. D., Schoebitz, M., Martorell, M., Goloshvili, T., Al-Harrasi, A., Al-Rawahi, A., Kumar, M., Suleria, H. A. R., Cho, W. C. 2021. Oxid Med Cell Longev, 2021, pages 1–20, doi: 10.1155/2021/5900422

6-MeO-harmalan is also an interesting β-carboline. I don't think it's been found in nature, but it's similar to the natural ones and it is hypothesized to be endogenous in humans. It was tested in combination with 5-MeO-DMT. More info: https://www.shroomery.org/forums/showflat.php/Number/29184532
 
Need a copy of this:

Review of β-carboline and its derivatives as selective MAO-A inhibitors. Benny, F., Kumar, S., Jayan, J., Abdelgawad, M. A., Ghoneim, M. M., Kumar, A., Manoharan, A., Susan, R., Sudevan, S. T., & Mathew, B. 2023. Archiv der Pharmazie, 356(7), e2300091. doi: 10.1002/ardp.202300091

Abstract

As flavin adenine dinucleotide (FAD)-dependent enzymes, monoamine oxidases (MAOs) catalyze the oxidative deamination of various endogenous and exogenous amines. MAO-A inhibitors are thought to be effective therapeutic agents for treating neurological diseases including depression and anxiety. Due to the academic challenge of developing new human (h) MAO-A inhibitors and the potential for discovering substances with remarkable properties compared to existing MAO-A inhibitors, numerous research groups are looking into novel classes of chemical compounds that may function as selective hMAO-A inhibitors. β-Carbolines are reported to be a prominent class of bioactive molecules exhibiting MAO-A inhibition. Chemically, β-carboline is a tricyclic pyrido-3,4-indole ring. It has only recently been discovered that this chemotype has highly effective and specific MAO-A inhibitory activity. In this review, structure-activity relationship studies included in particular research publications from the 1960s to the present are discussed with regard to β-carboline and its analogs. This comprehensive information helps to design and develop a new family of MAO-A inhibitors for the management of depressive disorders.
 
Need a copy of this:

Review of β-carboline and its derivatives as selective MAO-A inhibitors. Benny, F., Kumar, S., Jayan, J., Abdelgawad, M. A., Ghoneim, M. M., Kumar, A., Manoharan, A., Susan, R., Sudevan, S. T., & Mathew, B. 2023. Archiv der Pharmazie, 356(7), e2300091. doi: 10.1002/ardp.202300091

Abstract

As flavin adenine dinucleotide (FAD)-dependent enzymes, monoamine oxidases (MAOs) catalyze the oxidative deamination of various endogenous and exogenous amines. MAO-A inhibitors are thought to be effective therapeutic agents for treating neurological diseases including depression and anxiety. Due to the academic challenge of developing new human (h) MAO-A inhibitors and the potential for discovering substances with remarkable properties compared to existing MAO-A inhibitors, numerous research groups are looking into novel classes of chemical compounds that may function as selective hMAO-A inhibitors. β-Carbolines are reported to be a prominent class of bioactive molecules exhibiting MAO-A inhibition. Chemically, β-carboline is a tricyclic pyrido-3,4-indole ring. It has only recently been discovered that this chemotype has highly effective and specific MAO-A inhibitory activity. In this review, structure-activity relationship studies included in particular research publications from the 1960s to the present are discussed with regard to β-carboline and its analogs. This comprehensive information helps to design and develop a new family of MAO-A inhibitors for the management of depressive disorders.
Annas-archive has it.
 
While I personally prefer Banisteriopsis capii to Peganum harmala, I've used countless different MAO inhibitors of various kinds over the years, especially in comibination with (typically) serotonergics. Alicia anisopeta;a was one of the strangest I've ever used, and mixing Acorus calamus root (600mg gel cappeed) the day after a 10 strip, plus about 2g of D9 tincture had me tripping for another couple days. I've spent a lot of time with "lysergahuasca", "shroomahuasca", ayahusca, "pharmahuasca", and a handful of others, so if anybody has questions feel free to ask away!
 
Even though harmine and harmaline have a substantial "stoning" effect, they've never gained mass appeal and I suspect that one of the reasons is that people don't like the effect—I don't like the effect. But I see potential in the effect, it's just that it feels too crude and dirty. I wonder, do the molecules provide any insight into why they are like this? I think it would be awesome if we took this "crude oil" and turned it into "gasoline". And that's what Shulgin-type modifications are capable of doing. Can anybody hypothesize about how the molecule can be improved to give you a better stoning, or is that kind of a black hole until another Shulgin comes along and starts experimenting?
 
I always used moclobemide when eating DMT. The moclob didnt seem to have much effect on its own - its good for shroomahuasca.

I stopped taking oral DMT when I discovered 4-aco-dmt. I find 4-aco-dmt a vastly superior drug to oral DMT - it's a better, deeper, longer-lasting, more energetic trip than oral DMT and you can redose and keep tripping all day - and none of the horrendous nausea eating DMT causes.

(its got to be real 4-aco-dmt which is white/tan in colour tho, not the fake grey shit you get in the UK)
 
One of my DMT-Nexus posts that I figured I'd copy here.


Yes, people have micro/lowdosed both oral DMT and harmalas alone. Here is one quote:

subtle increase in visual acuity, focus ability, outlook, sexual energy, social outgoingness, creativity, meditation ability, openness to love in my heart, feeling lighter on my feet, feeling energy flow through me, and a sense of tapping into a larger wisdom of the world,

Warrior, 2013-10-23, Microdosing Ayahuasca Analogue (ACRB + SR)

Another one:

In large doses ayahuasca can produce very dramatic effects including visions and a substantially altered sense of perception but in these small doses it just wakens the brain up a little, enhancing mood, creativity, inspiration, visual perception, and practical effectiveness.

Holly Paige, http://foodforconsciousness.blogspot.com/p/reactivating-pineal-gland.html


@Sabnock1990 has a ton of experience with both:

in fact for awhile there i was trying to find a way to use Aya/oral DMT as a kind of daily vitamin or supplement/medicine because on DMT (at least during the peak once the come up settles down and stabilizes) i feel more sober than sober, i am functional, i can do things more easily that i have difficulties with in my day to day, i feel great on it lol, and not like the "oh bro i'm soooo high i feel amazing!!!" kinda great, i just feel naturally good, i feel pumped up and ready to go, i'm more intelligent on it, my language skills and word flow improves, i start using more sophisticated language and words that i didn't really know or would never really use, it brings out a more expansive and higher awareness/Consciousness within myself, and i feel that as a species we are desperately lacking that higher awareness/Consciousness, which if we had it in our day to day, shit would change up real quick lol, for the better.
2024-07-10, reddit.com/r/Ayahuasca


As for what led me to drink daily for 4 years lol, nothing really, it just felt like a constantly unfolding/ongoing connection and school of sorts, i didn't take it for any specific reason, i just took it to see what would happen and what all i could do with it. Me taking it so regularly just sorta naturally happened because due to the lack of tolerance i could just go deeper and deeper and let things continue to unfold and continue to advance amongst the different levels/layers of things, there's lots and lots and lots to learn in those states.

As for changes, all i can really say is what is commonly said, there's me before Ayahuasca, and then there's me after Ayahuasca, i'm in a completely different place within myself compared to where i was prior to Ayahuasca. A lot of the changes it's brought about are moreso internal even though there's some outward signs obviously lol. My working with Aya and the experiences and understandings i've gained through it has opened me up to a whole new world i never imagined existed prior to Ayahuasca, and a lot of it has stuck around, internally, even though it's hard to remember or even communicate/express/detail but deep down it's remembered, and anytime i take the medicine and reconnect to those states/spaces, all that knowledge and information and experience and understanding comes right back and you remember everything, so as some folks i've seen have mentioned, a lot of the memories and details and understandings are like state-specific, so you have to be in a certain state for that level of connection to come back up to the surface, kinda like dreams. As far as integration goes, that's of course been challenging, as it can be, but aside from my temper flare-ups from time to time (which again, i've come to link to my Folate deficiency i'm trying to correct), i'm a much better person for having worked with Ayahuasca and i owe my life to it, i absolutely do not know where i would be today had i not worked with Ayahuasca, so much has happened in my life because of working with Ayahuasca that i wouldn't be who i am today without it, it's been the only truly real thing in this very fake/false/illusory world of ours, that i've come across, nothing else compares to the level of depth and realness and Truth that comes to the surface while on Ayahuasca, it's real shit, not saying everything experienced is real, but when Truth strikes, you'll know lol.

So overall it was largely positive and beneficial and i had no negative/adverse effects/reactions to it, it's been the best medicine for someone like me, in fact i seem to be made for it, whether it's the Autism or my heritage or whether i was some shaman in a past life, idk, but i function pretty well on it and i feel right at Home with it, it's a natural part of our physiology anyways (DMT being natural to the body) so it's only natural that people feel at Home with it, it's a chemical messenger that connects us more deeply to ourselves on multiple levels and so it just feel natural, normal, right, it's only ever been a positive for me personally.
2024-07-10, reddit.com/r/Ayahuasca


In this post he mentions that he's taken harmalas in heavy doses for 12 years straight:

Also, it goes without saying, if it weren't for the DMT, Ayahuasca wouldn't really do anything, ya know? Have you taken Harmalas/Caapi/Rue on their own without DMT in heavy dosages? Sure there's some stuff there but it ain't DMT land lol. Ayahuasca needs an Entheogenic component, whether DMT, or mushrooms, or something else, even Cannabis can work in a bind if you're wired in a way for it to tap you into some of those aspects to some degree, you need a Light, otherwise the Harmalas are just medicinal and there's nothing really there, certainly nothing worth hundreds or thousands of dollars, or necessitating ceremonies, or anything even particularly spiritual, no action at all. If DMT was not in Ayahuasca, Ayahuasca wouldn't be sought out, at all, it would be completely uninteresting and unappealing, there'd be nothing there. So when you say "DMT trip", well, remove the DMT from the equation, and you don't have anything truly worthwhile.

The magick and the mysticism and the spiritual connection and all the stuff we can experience, the main action of Ayahuasca, comes from the DMT, even though the Ayahuasca effects come from the Harmalas, and so for example, Psilohuasca and Ayahuasca are both Ayahuasca even though you use different Light sources, but it's the Psychedelic/Entheogenic component that is the main element, even though the Harmalas are the main active ingredient, the DMT is the experiential component that without it there's just nothing really there, and this is coming from a guy who has taken Harmalas, in full/heavy dosages, daily pretty much, for 12 straight years and ongoing, speaking from extensive experience, there's not really much of anything to the Harmalas themselves without a Psychedelic component, and a lot of the things people experience with DMT/Ayahuasca can be experienced also with other Psychedelics/Entheogens, because it's the Psychedelic/Entheogenic component which is what gives the active effects, and so what you're really saying is that you don't seem to realize that the DMT is the most important aspect of Ayahuasca, so reducing it down to a "DMT trip" is a rather silly thing to do, because that's where all the magick comes from, without it, no magick.

Also, nevermind the fact that DMT is endogenous to the body and is very likely released at death, near-death, possibly birth and some other things, and is likely the source for spontaneous naturally occurring mystical experiences.

Btw, you can also orally activate DMT using Moclobemide, which gives you the exact same effects/experiences that you get when taking it with Harmalas, except that the Harmala effects are not in the equation, so you get to see what the DMT itself does without being filtered through the effects/synergy of the effects of the Harmalas. And i assure you, it's just the same and just like it is when using the Harmalas, so the main shebang definitely comes from the DMT, and to reduce DMT down to a "trip" is to do it a huge disservice and injustice, imo.
2024-07-10, reddit.com/r/Ayahuasca


For evidence that shows that harmalas have nootropic potential, see the bottom quote in this post: https://forum.dmt-nexus.me/threads/...n-v-carbolines-workthread.327067/post-3962597

Psychedelics also have nootropic potential:

Psychedelics Promote Structural and Functional Neural Plasticity. Ly C, Greb AC, Cameron LP, Wong JM, Barragan EV, Wilson PC, Burbach KF, Soltanzadeh Zarandi S, Sood A, Paddy MR, Duim WC, Dennis MY, McAllister AK, Ori-McKenney KM, Gray JA, Olson DE. Cell Rep. 2018 Jun 12;23(11):3170-3182. doi: 10.1016/j.celrep.2018.05.022


Psychedelic spurs growth of neural connections lost in depression. Bill Hathaway, Yale News, Jul 5, 2021


Psychedelic Mushrooms Reduced Human Cellular Aging by 57%, Increased Lifespan in Mice 30%. Andy Corbley. 2025-07-23. World at Large


Psilohuasca may be a much better option for mdosing than ayahuasca: https://forum.dmt-nexus.me/threads/...-tincture-for-microdosing.371025/post-3964770
 
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