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5,6-dibromo-N,N-DMT - the 'undersea' equation... Options
 
nen888
#1 Posted : 7/23/2011 12:38:18 PM
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..thought this paper on anti-depressant effects of 5,6-dibromo-N,N-dimethyltryptamine (from sea sponges) may be of interest if you haven't seen it....
http://pubs.acs.org/doi/abs/10.1021/np070371u
 

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Pandora
#2 Posted : 7/23/2011 12:56:35 PM

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Fascinating nen888. You are just a wealth of juicy information, aren't you? Thanks so much.

Sponges ftw!
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Seraph
#3 Posted : 7/23/2011 1:25:11 PM

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Is 5,6-Br-DMT hallucinogenic or not? Also wasn't there something about atoms on the '6' position of substituted tryptamines not doing anything? If having a 'Br' atom on the '6' position does make the psychoactive effects of the molecule different from 5-Br-DMT then that means that the '6' position does do something. So what is 6-HO-DMT like then?

How did they acquire these molecules from the sponges? Could members of this forum acquire 5-Br-DMT and 5,6-Br-DMT in the same way they did?

'while 5-bromo-N,N-dimethyltryptamine (2) caused significant reduction of locomotor activity indicative of a potential sedative action'

I think that indicates that 5-Br-DMT is a hallucinogenic similar to DMT, I think the reason it wasn't moving much was that is was tripping.
 
nen888
#4 Posted : 7/23/2011 1:48:37 PM
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..here's the publshed Bio-Assay recordshttp://pubchem.ncbi.nlm.nih.gov...say/assay.cgi?cid=360251, i'll do some more research...
 
nen888
#5 Posted : 10/19/2011 4:01:39 AM
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..i agree with seraph's comment that 5-bromo-DMT is probably psychedelic..
Shulgin and Voogelbreinder (2009) think it is probably psychoactive when taken in a similar fashion to DMT..there isn't any reason a Br substitution at this position would prevent or lessen activity..

some specimens of the sponge Smenospongia aurea yeilded primarily 5-bromo-DMT (at 0.88%) while other S. aurea contained mainly 5,6-dibromo-DMT, as well as 6-bromo-4'-N-demethylaplysinopsin [Tymiak et al. 1985]
S. cerebriformis (from Florida) contained 5,6-dibromo-DMT & ilimaquinone [Kochanowska 2008]
S. echina contained 0.95% 5,6-dibromo-DMT and trace new phenol
Polyfibrospongia maynardii yielded 5,6-dibromo-tryptamine & 5.6-dibromo-N-methyltryptamine
[Van Lear et al 1973] see also S. Voogelbreinder (2009) p.309-10..

.
 
endlessness
#6 Posted : 10/19/2011 11:26:10 AM

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And again thanks for this interesting thread nen!


Im attaching the paper quoted by nen in the first post:

Secondary Metabolites from Three Florida Sponges with Antidepressant Activity
J. Nat. Prod., 2008, 71 (2), pp 186–189
Kochanowska et al

Im also attaching the Hu et al paper about brominated tryptamines and 5-ht2 binding.



Also a bit more info to add (from Trout's Notes on simple tryptamines), plus molecular structures:

General safety note: Marine organisms often contain toxic/poisonous material. Wear protective clothing, do not bioassay plants without being fully aware of the components found and what you are doing. Also do note that evaluation of gramine analogs suggests 5-bromo compounds may be more toxic than parent compounds

Interesting fact: Hydrogenation of 5-Br-DMT and 5,6-dibromo-DMT gave DMT (Djura et al 1980)



5-Bromo-DMT



Soluble in ethanol, DCM, ethyl acetate

Activity: Unknown psychoactivity. Brominated tryptamines show a high affinity for human serotonin receptors (Hu et al. 2002. )

5-Br-DMT caused significant reduction of locomotor activity in the rodent FST model (suggested to indicate a potential sedative action). It did not show any antidepressant activity in either test. (Kochanowska et al. 2008 )

Sources:

Smenospongia aurea - collected in belize, only found in one of the two specimens collected at 0.68% dry weight, postulated it might be produced from symbionts that are not in all places where sponge grow (Djura et al 1980). Nen also posted the Tymiak et al reference.

Eudisoma fragum - sea-squirt from New Caledonia, 0.02% dry weight (Debitus et al 1988 )

Verongula rigida contained 5-Br-DMT (0.00142% dry wt.) (Kochanowska et al. 2008 )



5,6-dibromo-tryptamine




Activity: Unknown psychoactivity. Brominated tryptamines show a high affinity for human serotonin receptors (Hu et al. 2002. )
Shows antibiotic activity against gram negative and gram positive bacteria in vitro but not in vivo (Van Lear et al. 1973)

Sources:

Polyfibrospongia maynardi - Caribbean sponge




5,6-dibromo-N-methyltryptamine




Activity: Unknown psychoactivity. Brominated tryptamines show a high affinity for human serotonin receptors (Hu et al. 2002. )
Shows antibiotic activity against gram negative and gram positive bacteria in vitro but not in vivo (Van Lear et al. 1973)

Sources:

Polyfibrospongia maynardi - Caribbean sponge



5,6-dibromo-DMT



Soluble in ethanol, ethyl acetate.

Activity: Unknown psychoactivity. Brominated tryptamines show a high affinity for human serotonin receptors (Hu et al. 2002. )

5,6-diBr-DMT showed significant antidepressant activity in the Porsolt forced swim test in rodents and in the chick anxiety-depression continuum model. (Kochanowska et al. 2008 )

5,6-dibromo-N,N-dimethyltryptamine produced significant antidepressant-like activity in the forced swim test and in the tail suspension test. It did not induce hyperlocomotion indicating that nonspecific stimulant effects did not account for the observed antidepressant-like action. (Diers et al. 2008 )

Sources:

Smenospongia aurea
contained 5,6-diBr-DMT (over 0.2% dry wt.) and 4 other alkaloids. (Kochanowska et al. 2008 )

Smenospongia cerebriformis contained 5,6-diBr-DMT as a minor alkaloid. (Kochanowska et al. 2008 )

Verongula gigantea
had 5,6-diBr-DMT identified in one of five specimens analyzed via spectroscopic means. (Ciminiello P., et al. 2000)

Verongula rigida
contained 5,6-diBr-DMT (0.35% dry wt.) (Kochanowska et al. 2008 )
 
PrimalWisdom
#7 Posted : 10/19/2011 12:21:12 PM

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Interesting read Nen!!!

Go sponges!

Off-topic:
Am I the only one who sees the Domain unregistered. to view register at bit.ly/imageshack-domain thing instead of pics? I've noticed it appears in alot of threads. seems like the Nexus needs to register the site on imageshack or something?

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Ginkgo
#8 Posted : 10/19/2011 12:35:27 PM

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Wow this is interesting! I've heard about bromo-DMT before, but wasn't aware that it was so much information out there. Could you elaborate the claim "Also do note that evaluation of gramine analogs suggests 5-bromo compounds may be more toxic than parent compounds", endlessness? Do you refer to Beng et al. 1970, the article attached?
 
endlessness
#9 Posted : 10/19/2011 1:02:04 PM

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Hey Gingko!

Yeah, this warning was in Trout's notes and indeed the source was the paper you just attached. It says its an indication but clearly no proof, also we're dealing with animals there and not humans.

By the way, another interesting thing about these bromo compounds is that they could be from bacterial origin, not biosynthesized by the sponges, due to the presence in morphologically distinct areas of the sponges. (Kochanowska et al. 2008 )

PS: Can others see the images with the molecular structures or do they also get the image shack error?
 
joedirt
#10 Posted : 10/20/2011 12:06:43 AM

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Great find.

There is so much chemical diversity from natural products that has yet to be isolated it boggles the mind.

BTW I can see the images endless
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nen888
#11 Posted : 10/21/2011 5:10:19 AM
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endlessness wrote
Quote:
By the way, another interesting thing about these bromo compounds is that they could be from bacterial origin, not biosynthesized by the sponges, due to the presence in morphologically distinct areas of the sponges. (Kochanowska et al. 2008 )
..if such a bacteria could be found and cultivated..that could be the answer to world-wide mass DMT production..!
.
 
nen888
#12 Posted : 10/22/2011 4:21:41 AM
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..imagine a kind of entheogenic yoghurt in which bacteria convert tryptophan (from aging milk) into tryptamine and then DMT..the yoghurt is cultured for a few weeks then extracted..Smile

and if the Kochanowska et al. (2008 ) bacteria in Smenospongia hypothesis were correct,
then imagine being a sea-sponge..you find a nice spot in florida or the caribbean to set up for life,
and then you catch a bacteria that gives you (5br)DMT! ..permenantly..what a life..
.
 
Tordyveln
#13 Posted : 2/16/2012 3:49:49 PM

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nen888 wrote:
..imagine a kind of entheogenic yoghurt in which bacteria convert tryptophan (from aging milk) into tryptamine and then DMT..the yoghurt is cultured for a few weeks then extracted..


Here's a guy that show you how to alter yoghurt bacteria dna in your home.
Everything I write as Tordyveln is made up. I lie all the time.

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fidget
#14 Posted : 3/17/2012 3:48:21 PM
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This is interesting stuff...makes you wonder just what else is out there undiscovered in our oceans and rain forests.
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nen888
#15 Posted : 5/9/2012 3:21:34 AM
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Tordyvein wrote:
Quote:
Here's a guy that show you how to alter yoghurt bacteria dna in your home.
..thanks Tordyvein, you must've forgotten to add the link..here's the Hacking Yoghurt vid: http://www.youtube.com/watch?v=Co8NOnErrPU..very interesting..
.
 
nen888
#16 Posted : 5/9/2012 3:23:05 AM
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fidget wrote:
Quote:
makes you wonder just what else is out there undiscovered in our oceans and rain forests.
..as far as oceans go, i recall giant sea kelp seaweed contains DMT, some sea-cucumbers contain harmalas, and then there's the Norflok Island Dreamfish (see Psychoactive Animals thread)
.
 
Nicita
#17 Posted : 3/31/2013 11:18:25 PM

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I wanted to share something about 5,6-Bromo-DMT and hey, there a topic about it! Big grin

Bioassay report of a Chemist synthecising and bioassaying. Wink
 
InMotion
#18 Posted : 4/1/2013 8:50:35 PM
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Awesome post nicita! Thanks for that
 
nen888
#19 Posted : 4/2/2013 5:19:13 AM
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..yes, thank you nicitaSmile..really takes the thread forward..
 
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#20 Posted : 4/12/2013 8:05:57 PM

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heres the obvious question,

where can i get me some spongesTwisted Evil
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