2,4,6-tribromo-1,7-dimethoxy-N,N-dimethyltryptamine

[entheogenic-gnosis]

I came across this compound in my general research and was instantly intrigued, specially because of some of this compounds potential applications.

This tryptamine compound is present in aquatic invertebrates and is also known as "Convolutindole A"

2,4,6-tribromo-1,7-dimethoxy-N,N-dimethyltryptamine as well as other brominated tryptamine compounds like 5-bromo-DMT are common in some sea invertebrates and are being investigated for medical potential.

..."This chemical was tested for its ability to kill parasitic nematodes, It was found to be more effective than levamisole, a synthetic drug used to kill parasitic worms and to treat colon cancer".-Wikipedia

I heard that 5-bromo-DMT was also being investigated for anti-cancer research, but was also found to easily reduce to dimethyltryptamine. 5-bromo-DMT is found in a sea invertebrate as well.

Like lespedamine the NH group of the pyrrole ring of Convolutindole A has a methoxy group connected to it, as well as an additional methoxy group at position 7 and bromine atoms at 2, 4 and 6, a fascinating compound...

-EG

 

[downwardsfromzero]

Structural formula attached

Interesting stuff, them marine indoles.

Edit: that doesn't seem to have worked for some reason, trying again.

 

[downwardsfromzero]

Another attempt with structure diagram...

This has a transparent background, will show up if downloaded.

 

[entheogenic-gnosis]

I could not get the picture deal to work, but thank you for posting it, if there are continuing issues I can find a structural representation to attach.

substituted dimethyltryptamine compounds have some medical history, such as the "triptan" compounds (rizatriptan, Sumaritan, zolmatriptan, etc..) So I can't wait until more research is done regarding these brominated tryptamines being found in these sea invertabrates.

It's crazy how bromine shows up so much in these sea invertebrates endogenous compounds, there's far more chlorine in the ocean...

In the DMT extensions and commentary section of TIHKAL shulgin mentions these brominated tryptamines:

Two additional ring-substituted derivatives of DMT come from the marine world. 5-Bromo-DMT and 5,6-dibromo-DMT are found in the sponges Smenospongia auria and S. echina resp. I have no idea if they are active by smoking (the 5-Br-DMT just might be) but they are quantitatively reduced to DMT by stirring under hydrogen in methanol, in the presence of palladium on charcoal. A very closely related sponge, Polyfibrospongia maynardii, contains the very closely related 5,6-dibromotryptamine and the corresponding monomethyl NMT. I had the fantasy of trying to scotch the rumor I'm about to start, that all the hippies of the San Francisco Bay Area were heading to the Caribbean with packets of Zig-Zag papers, to hit the sponge trade with a psychedelic fervor. This is not true. I refuse to take credit for this myth.-TIHKAL;shulgin

Here shulgin mentions another 1-methoxy substituted DMT,lespedamine:

The compound with a methoxy group substituent at the 1-position is called Lespedamine, 1-MeO-DMT. With an NO bond, this should be classified as a substituted hydroxylamine. I would love to know if anyone anywhere has ever tried smoking it. I suspect it might very well be active, but it is, to my knowledge, untried.-shulgin; TIHKAL
(which I only mention because of this fact: The researchers who discovered the chemical drew specific attention to the methoxy group at the indole 1-position (attached to the nitrogen atom in the pentagonal ring) as being an unknown occurrence in the marine world until recently-Wikipedia)



There's some fascinating compounds being found in these sea invertebrates!


Plakohypaphorines are iodine-containing indole alkaloids named for their similarity to hypaphorine, another alkaloid related to the amino acid tryptophan.-Wikipedia

These are similar to tryptophan, only with three methyl groups off the amine nitrogen and iodo substitutions on the indole ring...These interested me because they are found in marine invertabrates and are similar to a newly discovered tryptamine found in a fungi (Inocybe aeruginascens) called "Aeruginascin" (N,N,N-trimethyl-4-phosphoryloxytryptamine) which shares this same trimethyl substitution on the amine nitrogen with the Plakohypaphorines.

the marine bryozoan Flustra foliacea produces another 2-substituted brominated tryptamine, 2-[6-bromo-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]-N-methylethanamine also known as "Desformylflustrabromine"
"dFBr has been identified as a novel positive allosteric modulator of neuronal nicotinic acetylcholine receptor with sub-type specificity for heteromeric receptor with no effect on homomeric sub-type"-Wikipedia
...some novel pharmacology for a brominated tryptamine, plus dfbr has a novel substitution at the two position and is found in yet another sea invertabrate.

Sorry I'm a bit all over the place in this post, I've been doing quite a bit if research, and it's hard to organize it all into a quick post, but I have found these marine invertebrates to be fascinating chemists, producing all sorts of novel treasures.

-EG

 

[entheogenic-gnosis]

I found a depiction of the compound, which I have nit lost interest in...

1-methoxyindoles like Lespedamine occur in Legumes, some 1-methoxyindoles can be found in animals, but "Convolutindole A" (2,4,6-tribromo-1,7-dimethoxy-N,N-dimethyltryptamine) was one of the first 1-methoxyindoles to be found present in aquatic invertebrates.

-eg

 

[entheogenic-gnosis]

Sorry, all the depictions I tried to download would not work, so I had to do it by hand.

I'll try one more of the downloads followed by my hand drawn depiction.


-eg

 

[Ulim]

Use Chemspider you just need to dump the compound name into the search bar.

I dont think this one is active in any way. The Bromine is just way to big but eh we never no if it can be a prodrug in the body!

 

[entheogenic-gnosis]

Use Chemspider you just need to dump the compound name into the search bar.

I dont think this one is active in any way. The Bromine is just way to big but eh we never no if it can be a prodrug in the body!

From chemspider it kept saving it as an .ashx file, or something, which I can't post here...

plus I'm on a tablet, not a PC or laptop, so I don't have those capabilities.

I don't mind depicting molecules by hand, shulgin called them "dirty pictures" because of how intimately one knows the molecule after understanding the subtleties of its structure, by depicting the molecule by hand it's like building it atom by atom, you really get to know it

I think my molecules are depicted in grater detail, I write out my alkyl substitutions and side chains rather than using line representations, plus with the chemspider version, while 100% correct, is depicted upside down.

I prefer to depict things by hand, it's so much faster and easier...my penmanship isn't that bad is it?

-eg

 

[entheogenic-gnosis]

Use Chemspider you just need to dump the compound name into the search bar.

I dont think this one is active in any way. The Bromine is just way to big but eh we never no if it can be a prodrug in the body!

This chemical was tested for its ability to kill parasitic nematodes, It was found to be more effective than levamisole, a synthetic drug used to kill parasitic worms and to treat colon cancer. -Wikipedia

My interest here was not in an active psychedelic, but in an anti-cancer medication.

There are plenty of natural halogenated compounds present in marine invertebrates, many with massive potentials in medicines*, then finding that one of these brominated compounds also contained a DMT moiety is what drew me to Convolutindole A.

*

Abstract: This review presents the biological activity—antibacterial, antifungal, anti-parasitic, antiviral, antitumor, antiinflammatory, antioxidant, and enzymatic activity—of halogenated marine natural products discovered in the past five years. Newly discovered examples that do not report biological activity are not included.

Biological Activity of Recently Discovered Halogenated Marine Natural Products

This review presents the biological activity—antibacterial, antifungal, anti-parasitic, antiviral, antitumor, antiinflammatory, antioxidant, and enzymatic activity—of halogenated marine natural products discovered in the past five years. Newly discovered examples that do not report biological...

www.mdpi.com

-eg

 

[entheogenic-gnosis]

Here shulgin comments on 5-bromo-N,N-dimethyltryptamine, a related compound found in sea invertebrates mentioned in my initial post.

Two additional ring-substituted derivatives of DMT come from the marine world. 5-Bromo-DMT and 5,6-dibromo-DMT are found in the sponges Smenospongia auria and S. echina resp. I have no idea if they are active by smoking (the 5-Br-DMT just might be) but they are quantitatively reduced to DMT by stirring under hydrogen in methanol, in the presence of palladium on charcoal. A very closely related sponge, Polyfibrospongia maynardii, contains the very closely related 5,6-dibromotryptamine and the corresponding monomethyl NMT. I had the fantasy of trying to scotch the rumor I'm about to start, that all the hippies of the San Francisco Bay Area were heading to the Caribbean with packets of Zig-Zag papers, to hit the sponge trade with a psychedelic fervor. This is not true. I refuse to take credit for this myth. -TIHKAL;shulgin

Here shulgin mentions the related 1-methoxy-DMT, or "lespedamine"

The compound with a methoxy group substituent at the 1-position is called Lespedamine, 1-MeO-DMT. With an NO bond, this should be classified as a substituted hydroxylamine. I would love to know if anyone anywhere has ever tried smoking it. I suspect it might very well be active, but it is, to my knowledge, untried. I wonder why it deserves a trivial name, vis., Lespedamine? TIHKAL; shulgin

To answer shulgins question regarding the name "lespedamine", I want to mention that the compound is found in the plant "Lespedeza bicolor" so "lesped-amine" is clearly referencing this.

-eg