They live in the gulf of mexico, and turn dark purple when exposed to oxygen.
(Hm, kind of like magic mushrooms Hopefully they are overpopulated )

WOW!!!! I see these sponges all the time when i dive around where I live and I never knew they contained DMT/DMT analogues. Unfortunately, I don't want to harvest them because harvesting sponges is a felony where I live and do not want to risk pissing off the local marine patrol. If any nexian gets the guts to procure some sponges and extract some 5,6 Bromo DMT from these guys please let us know how it works out! I'm listening with all three of my ears.

I'm no chemist, but I woner if the Bromo makes the hallucinogen inactive, I only have one relative example which is 2Bromo-LSD which is not a hallucinogen but shows promise for Cluster Headache Treatment. http://en.wikipedia.org/wiki/2-Bromo-LSD

Come on, who is going to be the first to try and smoalk a bowl of sponge? *Taps foot*.

Well, Bromo-DragonFLY and 2C-B are obviously both active, so a bromine atom in a compounds chemical makeup is not enough to render a compound inactive.

But I'm also no chemist, so I don't know how the position of the bromine atom(s) might alter a compound's potential for activity.

Ah thanks I forgot about those guys have Bromo attachments

Given that DMT is active when a variety of other functional groups are stuck on the 5 position, I would expect 5-Br-DMT, although depending on how DMT binds to 5-HT receptors, the size of the Br group might cause steric strain. Does anyone know exactly what the active site on the 5-HT2AR (or any other 5-HTRs) looks like?

Nichols did a lot of work looking at the activity of various substituted hallucinogenic tryptamines. Here's the abstract, I'll post the full text when I have a moment to dig it up
http://www.ncbi.nlm.nih.gov/pubmed/11101361

^^^
..we have this first known bioassay report of 5-Br-DMT (p.1) , with activity, apparently about half the potency of DMT..

Nice, I had thought that was looking at 5,6-Br-DMT, not just 5-Br-DMT.

Where does Hamilton work that he has access to GC-MS and NMR for random samples of drugs?

Does anyone on this forum have the faintest idea as to how to extract alkaloid from sponges? I found GOADS of these sponges growing all over some rocks down the street from my place and was wondering if anyone here had any experience with extracting from sea life. Should I do several freeze and thaws before hand, blend sponge prior to boiling, and what solvent should i use, etc etc? The bioassays sounded promising and colorful results from this molecule and I cannot wait to begin my journey with it!

Hold your horses there. Before you start extracting from mystery sponges, you should 1) double check the identity of the sponge, and 2) make sure there's nothing toxic in the sponges in addition to the tryptamines that you might pull.

In theory though, an extraction from a sponge would work like any normal extraction. Just stick them in a blender.

I'm sure *everyone* would love to know what you find.

If we have a reliable source for 5-Br-DMT, that could make getting the various substituats of DMT much easier. There are tons of reactions that will allow you to replace the halide with a functional group like hydroxy or methoxy. 5-MeO for the masses!

There are not necessarily 'tons' of reactions that would a) do this without turning the indole into a tarry mess and/or b) be easily achievable by the kitchen chemist.

Also, you'd better start farming and nurturing these poor critters before setting off (yet another) extinction just because some of you 'want to get high'.

Try breath exercises first (it will help with the sponge diving, after all )

interesting...
are there any known Km values for this compound?

depends on the bulkiness of the overall molecule. halides are quite bulky themselves

How do you tell from sight what kinds of molecules will have activity at certain receptors? Do you know that shape of the active site of the 5-HT2A? I also see people do this with opioid drugs, saying "XYZ will obviously be more potent because the ABC in the 123 position."

that's precisely how it's done, using visualization programs like Pymol, Sybyl, and Discovery Studio.
Of course, the molecule has to fit in the binding pocket of the active site. Inhibitors typically bind allosteric sites.

it's not always cut-and-dry by looking at what position a functional group is, if a compound will be active or not, especially when stereochemistry is involved.

Do you mind if I keep asking you questions? I'm trying to study molecular neuroscience at school, but these questions about psychopharmacology are a little beyond the professors I'm currently talking to.

What causes some molecules with similar binding profiles to have different effects? DMT and 5-MeO-DMT are both 5-HT2AR agonists, but produce subjectively dissimilar effects. I know things like the rate at which a molecule crosses the BBB can effect things like come-up intensity, but variations in how visual a drug is (like N,N vs. 5-MeO) seem like they would be caused by something else.

I also know there are 5-HT2AR agonists that don't have psychedelic effects.

Is it possible that different molecules change protein conformation in different ways, causing different downstream effects?

yes.

some may act allosterically as partial antagonists on receptors. this is common with structurally complex molecules, like ibogaine and LSD, which display stereochemistry. this may account for the various somatic effects experienced, and why higher doses inhibit some effects, and enhance others.

one of the central tenets in biochemistry is that structure determines function; and while this is largely used to describe macromolecules (proteins), this also applies to ligands (small molecules).

^..what benzyme says,

and also the compounds to do not merely act on the 5HT2 receptors (which themselves have a number a sub-types eliciting different CNS and physiologic functions)..they act on other receptors as well..e.g. DMT and NMT are also TAAR1 agonists, amongst other things..

(ps. Km values of 5-Br-DMT i do not know of)