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Tryptoline Psychedelics?

Ham-milton

Ham-milton

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I was wondering if anyone had any knowledge of any tryptoline based psychedelics. The conformationally constrained NMT analogue is an MAOI and SNRI. That sounds like a dangerous situation, but it inhibits the reuptake of 5HT most preferentially, I think.
200px-Tryptoline_structure.png


Has there been any research into these as potential drugs of abuse (specifically if any analogues have any appreciable affinity for 5HT2a or causes an SE release).
 
Okay, this is kind of confusing to me. So tryptoline is a beta-carboline?

Okay, Wikipedia has explained this to me now.
bcarbolinecomparisonat0.jpg


So THH is the only tryptoline that's psychedelic? Or are there others? I'm only interested in those with the bond arrangement of tryptoline because they have most in common with tryptamine, I think. Or does the addition of double bonds in there alter the configuration in a positive way?
 
Harmine isn't a tryptoline, though. It has double bonds where tryptoline has none. Shulgin's right, though, the naming of these is really difficult and needlessly complicated.
 
Ham-milton said:
I'm only interested in those with the bond arrangement of tryptoline because they have most in common with tryptamine, I think. Or does the addition of double bonds in there alter the configuration in a positive way?
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The additional double bond(s) in harmine/harmaline flattens out the third ring. I don't have any idea if this is favourable for psychoactive effects... As far as the fully dehydrogenated derivative (i.e. harmine) isn't psychoactive but just "psychomodulating" (...MAOI), I would guess that sp3-hybrids like in THH are a good idea. Sorry, but no refs at hand.

Peace! Murphy

Edit: Also consider that you change a hydrogen bridge donor (-NH-) for an acceptor (=N-) when making the third ring aromatic. This could be important for the binding mode in the target...
 
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they are all B-carbolines. as this is the parent ring structure.
tryptoline is tetrahydrobetacarboline

these don't really seem to be psychedelic on their own though for a while harmine was thought to be psychedelic, In my opinion it is more a wavy vomiting toxic delerium. Some of them are dangerously neurotoxic.
 
vecktor said:
In my opinion it is more a wavy vomiting toxic delerium
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OK, that clears it out. Thx. Sounds like "fantastic" stuff. Like my QNB-thread in the other forum ;)
 
vecktor said:
these don't really seem to be psychedelic on their own though for a while harmine was thought to be psychedelic, In my opinion it is more a wavy vomiting toxic delerium. Some of them are dangerously neurotoxic.
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How interesting i didnt know until now that MPP+ is a beta carboline.

I must testify on behalf of Banisteriopsis caapi though, it is indeed psychedelic in it own right, i have consumed a highly concentrated b. caapi brew sans DMT contributing plants and was astounded by just how psychedelic it was. It felt like the onset of a mushroom trip, euphoria that caught me by surprise, wild color enhancement, i even remarked to my girlfriend at the time that i couldent believe it was not a popular recreational drug! Minutes later the euphoria became nausea, and i spent the rest of the night in the fetal position, vomiting on the bathroom floor and having ominous closed eye visuals.
 
hamhurricane said:
How interesting i didnt know until now that MPP+ is a beta carboline.
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Who said that?! It isn't.

You're definitively wrong here...somehow...:\
 
MPTP which is the actual dangerous species which makes MPP+ in vivo, theoretically MPP+ cannot hurt even if you inject it unless you get it past the BBB not that I would want to test the theory, and the betacarbolnes are close cousins, if a nitrogen bridge is made between the piperidine and phenyl of MPTP you get a tetrahydrobetacarboline, and yes this betacarboline is an effective DA neurotoxin too. it is this 'derivative' of MPTP that shulgin refers to in the back of Pihkal. there are also some pretty effective isoquinoline neurotoxins which work the same way, by becoming permanently charged inside the the brain so they can't get back out and then they spin out free radicals as the oxidase system tries to chew them up

does B caapi contain tryptamines as well as carbolines? or am I thinking of some other South American plant.

My only harmine experience was with material extracted from Aldricha chimica and it was delerium. perhaps Rue or B caapi are kinder materials though rue contains some other unpleasant alkaloids.
 
I've had the extracted stuff too, and I thought it was pretty cool stuff. I think psychedelic beta carbolines are a far better explanation for dreaming- my experience with the extract was really close to dreaming.

Not in a bad way- my mind was totally normal, but the visuals were way freaking intense and very similar to dreaming.
 
vecktor said:
does B caapi contain tryptamines as well as carbolines? or am I thinking of some other South American plant.
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Mimosa Hostilis contains tryptamines and a relatively new and still vaguely understood chemicals called yuremamine which gives the DMT oral activity but is not necessarily a MAOI or a betacarboline...

Yurema is still used for its psychoactive properties in traditional religions in Brazil [1]. However, a pharmacological explanation for the visionary effects from this sacred beverage is lacking, as DMT is not orally active because of its rapid enzymatic metabolism by MAO. [...] It is suggested herein that intramolecular hydrogen bonding of the tertiary aliphatic nitrogen of yuremamine protects it from metabolism and could allow it to act as an inhibitor of MAO, thus facilitating the oral activity of DMT in this single-plant formulation. Presently the putative pharmacology of purified yuremamine is unknown.
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Is it known if the activity is the result of yuremamine and not DMT? I sort of doubt that it's an MAOI, considering it has nothing in common with the MAOI beta carbolines. How many different structures, based around the central structure, can still result in MAOI activity?

It sure looks like a possibly active psychedelic, though it really is an oddity.

Is that drawn right? It has a quaternary nitrogen?
th.Yuremamine.jpg
 
It seems reasonable using the Pictet-Spengler reaction to form these in good yields. I'd imagine that the dotted line is simply showing the hydrogen bonding employed between the lone pair on the N and the partial positive charge on the H. Otherwise I'd expect to see an ammonium cation...
 
oh, so the hydrogen is on the oxygen and the nitrogen? Does this force that part of the molecule into a rigid form?
 
Well the hydrogen is bonded to the O, but because the electronegativity of the O pulls the electron density away from the H it creates a partial positive charge. The H isn't bonded to the N, but like I said, I'd imagine that the dotted line is showing the concept of hydrogen bonding (one reason why water has such a high boiling point, unlike other weak intermolecular forces - aka van der waals forces). I would guess this would keep it in a more rigid form, yes.
 
immaturepoop said:
I would guess this would keep it in a more rigid form, yes.
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I agree, albeit only to a very small degree. The resulting cycle is far to big to be stable. It would be even more rigid if the resulting cycle would be a 5- or 6-membered ring.

The suggested protection from metabolic degradation (for yuremamine) by this hydrogen-bond is very unlikely. It's a fairly weak bond and would be opened easily on its own or by enzymatic means.
 
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After doing a little more searching, I wonder if some of these will be inactive psychedelics because of ability to deplete catecholamines.

they're pretty similar to reserpine
220px-Reserpine.png
 
Are beta carbolines like the harmala alkaloids in ayahuasca toxic??

Mammalian brain has a beta-carboline 2N-methyltransferase activity that converts beta-carbolines, such as norharman and harman, into 2N-methylated beta-carbolinium cations, which are structural and functional analogs of the Parkinsonian-inducing toxin 1-methyl-4-phenylpyridinium cation (MPP+).
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