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DMT Isoforms?

Morninggloryseed

Morninggloryseed

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DMT Isoforms, and beta-keto tryptamines?

In a paper that rebutes Ott's claims that bufotenine (5-HO-DMT) is a psychedelic, it is mentioned the existence of 'isoforms' of DMT and bufotenine.

http://www.erowid.org/archive/sonoran_desert_toad/pipe.htm

Ott's experiments with isolated free-base bufotenine placed the melting point at about 124-126° C. However he points out that others have reported isoforms melting from [123-]124-126[-129]° C and 146-147[-150]° C from isolated material and 146-147° C and 138-140° C from synthetic material. This suggests that there are three isoforms, and the melting point may vary depending on what one has on hand. Citing Shulgin & Shulgin 1997, Ott also mentions that three distinct DMT isoforms with melting points ranging from 44-74° C have been reported (Ott 2001), and at least two of these forms have been produced by the drug underground (Sand 2000). As well as different isoforms creating different melting points, the method of crystallization, purity, and several other factors can affect the melting point. 5-MeO-DMT has been listed as having a melting point of 67.5-68.5° C (Ott 1996). It is also worth noting that different salts will have different melting points.
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So we have mention of three 'isoforms.' What are these? I can imagine one...

DMT_ISOFORMS.jpg


Does anyone have a clue what the two others are? There is mention of two appearing on the market before! News to me. That suggests psychoactivity.

And another author went on to suggest it was one of these isoforms of bufotenine that caused the psychoactivity that Ott attritubed to the classic bufotenine (which that author contends is not a psychedelic.)

I did a search for the compound, the bufotenine analogue, and a few others and came up empty handed. I'm curious what some here think of these. Could they be a new family of psychedelics?

Also, someone wrote me asking about beta-keto tryptamines.

keto-tryptamine.jpg


If you follow the Nichols theory, then the tryptamine keto group is in the 'wrong' place to have the same interactions as an beta-oxygenated group on a PEA. But it makes a neat thing to think about.
 
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Another quick idea....cyclopropyl and butyl tryptamines. I was thinking since the same change on DOM did not abolish activity (although it did reduce potency), that perhaps these would be active along the same lines as a-MT or perhaps a-ET. I just drew them without regards to which stereoisomer would be best, as I did not know.

cyclo-indoles.jpg
 
Where, who what? WHich compound do you refer? :) This is really three threads in one, I just didn't want to clutter the forum.

DMT isoforms, beta-keto tryptamines, and 'cyclotryptamines'
 
Well I wasn't looking to smoke them (in theory if it was in front of me). I would be curious about their oral activity, or IM if not orally active.
 
I can't see MAO getting its teeth around either of the cyclotryptamines, but I'd be amazed if their activity was near that of AMT, especially considering the myriad of isomers.

Very interesting to see what effect the change in bond lengths/angles and possible conformers (and hence placement of the terminal amine in relation to the indole ring) would have though!
 
No, just drew it as a basis of comparison. bk-MDMA has a phenethylamine skeleton. I don't think the bk-tryptamines would have the same relationship to their unsubstituted analogues as the bk-PEAs do because the bk-tryptamines have the oxygen in the 'wrong' place, at least as far as my understanding goes.

So would the bk-MDMA be considerd a tryptamine? Still learning here lol.
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Yes, the key would be to try the racemates of the cis, then the trans, then the four individual isomers. But I bet someone here would have the brains to see which confirmation would best fit.

UnfortunateSquid said:
I can't see MAO getting its teeth around either of the cyclotryptamines, but I'd be amazed if their activity was near that of AMT, especially considering the myriad of isomers.

Very interesting to see what effect the change in bond lengths/angles and possible conformers (and hence placement of the terminal amine in relation to the indole ring) would have though!
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isoforms

I am not certion but I think Ott is referring to different crystal forms of DMT polymorphs, which is my chemistry understanding of isoforms rather than different structures (which is the recent biology use): which are isomers. this is analogous to say graphite and diamond (allotropes) or the different crystal forms of calcium carbonate: aragonite and whatever the other one is. same chemical, different crystal structure

I believe most of the alleged DMT isoforms are not true polymorphs or true isoforms rather they are due to impurities lowering the melting point and the ease with which freebase DMT entrains solvent when crystalising.

2CB hydrochloride is another perhaps better example of a polymorphic salt, it exists in at least two forms with different melting points depending on whether it is recrystalised from isopropanol or from water. both salts are anhydrous and pure but the crystal shape is different.

the idea that one isoform is psychoactive and another isn't is wierd and wrong, unless the term isoform is being used in a unusual way. because all isoforms will dissolve in water eventually to give exactly the same solution. unless you believe in the hippy shit concept of molecular memory and crystal energy.
 
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^I'm w/ vecktor, I always thought isoforms referred to the xtal packing or even xtal type, ie, hydrated salts vs "pure" salts.
 
Well, what does the author mean when he says a different isoform would be responsible for the intoxication reported, since he believes bufotenine is inactive? I'm confused.
 
UnfortunateSquid said:
I can't see MAO getting its teeth around either of the cyclotryptamines, but I'd be amazed if their activity was near that of AMT, especially considering the myriad of isomers.
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Is 4 a myriad, or am I missing something? Since MAO is DMTs enemy, thus a short trip, even only 1 isomer cyclotryptamines were active wouldn't it make for a longer time to come on, but potent compounds (the two thing cancelling each other out)?

If you look at the DMT skeleton buried in the LSD molecule, Shulgin noted that the 8-ethyl was twice as potent, so if we are going crazy, I vote for methyl, ethyl.
 
morninggloryseed said:
Well, what does the author mean when he says a different isoform would be responsible for the intoxication reported, since he believes bufotenine is inactive? I'm confused.
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Not as confused as me, :)
I really don't know. the way I see it and most chemists and pharmacologists too, is bufotenine is chemically 5-hydroxy NN dimethyl tryptamine if its not that then it isn't bufotenine, There has been plenty of confusion regarding dehydrobufotenine which is an extraction artifact of bufotenine and which is believed to be psychoactive rather than a violent poison dehydrobufotenine chemically and pharmacologically its a different chemical with a different structure, it isn't even an isomer of bufotenine.

I have not read the original source of the quote, but the psychedelic literature is full of tie dye authors regurgutating stuff they haven't made the effort to understand. if i get to read the original source then it might all be a bit clearer. bit I suspect there is a loss in transmission problem here.

Bufotenine in any of its isoforms will form bufotenine vapour when heated and inhaled, the vapour is exactly the same for all isoforms, so it does sound ver implausible that one isoform is active and the others aren't.
 
haribo1 said:
Is 4 a myriad, or am I missing something? Since MAO is DMTs enemy, thus a short trip, even only 1 isomer cyclotryptamines were active wouldn't it make for a longer time to come on, but potent compounds (the two thing cancelling each other out)?

If you look at the DMT skeleton buried in the LSD molecule, Shulgin noted that the 8-ethyl was twice as potent, so if we are going crazy, I vote for methyl, ethyl.
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There are only 4, but 4 is enough of a myriad when it comes to separating them!

I was comparing the compounds to alpha-methyl tryptamine, not DMT. Comparing the potency and effects of a non-orally-active compound like DMT to a most likely orally active compound such as the cyclotryptamines discussed here is difficult at best.

Are you refering to 8-ethyl DMT or 8-ethyl LSD? And which is the 8-position?

As to the 'isoform' debate, I've never heard the word isoform used to refer to anything but minor variants of proteins. But, having read the original citation again, it looks more like different crystal structures, rather than different isomers, which would lead to the different melting points observed (perhaps higher smoked potencies for the lower melting point isoforms, due to less material being combusted in the solid phase? Certainly not different effects anyway). Does the paper actually mention anything about different effects/potencies of the various isoforms? The section posted above doesn't, as far as I can see.
 
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I think he means 6 ethyl LSD, as 8 ethyl lysergic acid is known but unlikely to be synthesised.
 
yep... I'm poor at counting, 6 position of the Lysergic Acid Molecule8 8(
 
i know this is an old thread and I'm sure if this has been clarified elsewhere buy in reffering to cycloalkyltryptamines cyclopropyltryptamine has been made. It's a very potent maoi but nothing is mentioned about any psychoactivity/psychedelia/or any interaction with 5HT. This seems to correlate with the PEAs like tranylcypromine. Perhaps if it had another sub on the nitrogen, something like N,N-MethylCyclopropyl-T, I wonder if taking L-Me with nnCPT would biosynth nnMCPT.
 
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