Drug info - 25i-nboh

[Synesthesiac]

This one is a MUCH more potent version of the very popular 2C-I, though it is very new and probably not easily available. Someone swim knows said he is in the process of trying to aquire it from a certain university. Though since it has no history of human consumption hardly at all, it would be highly advisable not to jump in the deep end with this one if one were to aquire it.

25I-NBOH

25I-NBOH or N-(2-hydroxybenzyl)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminoethane is a derivative of the phenethylamine derived hallucinogen 2C-I, discovered in 2006 by a team at Purdue University. It acts as a potent agonist for the 5HT2A receptor with a Ki of 0.12nM at the human 5HT2A receptor, making it some 5x the potency of 2C-I itself. In vitro tests showed this compound acted as an agonist but animal studies have not been reported. Interestingly while the N-benzyl derivatives of 2C-I were significantly increased in potency compared to 2C-I, the N-benzyl derivatives of DOI were inactive.[1]

1. Braden MR, Parrish JC, Naylor JC, Nichols DE. Molecular Interaction of Serotonin 5-HT2A Receptor Residues Phe339(6.51) and Phe340(6.52) with Superpotent N-Benzyl Phenethylamine Agonists. Molecular Pharmacology. 2006 Dec;70(6):1956-64. Archive link: http://www.drugs-forum.com/forum/loc...tid=35&id=4836

Source: wikipedia

Reputation Comments on this post:

Thank you for editing this post to increase the safety of thie thread. I appreciate your interest in these chemicals and...

[RaverHippie]

definitely looks interesting and quite the treat for anyone who is able to acquire some for their lab rats.

[Waste]

Surely as this is a derivative of the phens, it would fall under the analogue act?

[RaverHippie]

i would assume it"s too far removed to be considered an analog when considering the language of the law

n hydroxybenzyl 2C-I

[Waste]

Any more info on this one?

[Shampoo]

Nichols stopped aiming to produce 5-HT agonists with pleasant/psychedelic effects some time ago, namely after the publication of the (in)famous pihkal and Shulgin's subsequent treat, tihkal.

The Ki of this one seems pretty low, perhaps to the point where it may be...oh, I dont know... a research tool? and not a psychedelic drug?

Br-dfly and other benzodifuran derivatives (especially fully planar dfly derivatives), as well as 25I-NBOH, 25I-NBOMe, TCB-2 and the rest of the illustrious products of the Nichols/Purdue lab which have ultrapotent/sub-milligram agonist activity are not toys.

These are tools for probing receptor activity, specifically and only 5-HT-2A/sometimesC receptors. They bind with an unbelievable affinity to these receptors and are thus very useful in research, not on blotters. Stay away from these chemicals. They are not formally tested in humans in any published document (not even rogue psychonaut publishing a la Alexander Shulgin), and may have long lasting, intense effects that may not be pleasant. Enzyme assays have yet to be done either, and we have no idea what the natural byproducts of the enzymatic degradation of these compounds are: for all we know (though unlikely), the compounds resulting from 25I-NBOH degradation could be potent neurotoxins.

If you must know however, unmonitored human trials have taken place under non-experimental conditions:

General consensus seems to be that 25I-NBOH shows no oral activity.

*Activity via sublingual or parenteral starts at well below one milligram (full activity at 500-700µg) and may be fatal in high doses.

*Doses lower than one milligram have reported some visual and cognitive activity, though reports are not detailed/well-defined.

*Doses above one-two milligram(s) have produced profound effects including severe confusion, disorientation, and overwhelming visual distortions.

*Doses of more than three milligrams may produce seizures and doses of less than ten milligrams may be fatal (shown in other n-benzyl derivatives).


I would say stay away from these ones until more is known, but if you or your friends decide to dive in, document everything, if nothing else than for the enrichment of human knowledge.

But seriously, leave the hyperpotent receptor agonists to the neuroscientists/neuropharmacologists. These are- in so many words- not to be 'played' with.

Reputation Comments on this post:

	Very informative post, thank you :)
	very useful information here Shampoo
	A very valuable safety advice. Thanks.

[Waste]

Excellent post, SWIM will be leaving this one to the braver researchers, he's not a fan of taking chemicals with very little background knowledge

[Synesthesiac]

They are not formally tested in humans in any published document (not even rogue psychonaut publishing a la Alexander Shulgin)

rogue psychonaut.

Please Explain.

What would define a rogue psychonaught from a normal psychonaught?

I would say stay away from these ones until more is known, but if you or your friends decide to dive in, document everything, if nothing else than for the enrichment of human knowledge.

I am for one not going to be trying this for sure, bearing in mind what you have said. And someone who isn't me does have some now which one of his friends, with near unrivalled knowledge of chemistry, synthed himself after I had a chat with him. But swim thinks its going to be destined as another chemical to put in the 'potentially dangerous' chemical drawer of his lab, not to be tried unless curiousity gets the better of him.

But seriously, leave the hyperpotent receptor agonists to the neuroscientists/neuropharmacologists. These are- in so many words- not to be 'played' with.

Agreed. Edited the OP to make it seem like less of a good idea for anyone to try this one.

Could I please enquire as to your background in this area? You have a degree in pharmacology, or a related area, I presume?

[Shampoo]

Originally Posted by Synesthesiac

rogue psychonaut.

Please Explain.

What would define a rogue psychonaught from a normal psychonaught

I suppose I should correct that. Shulgin is not so much a rogue psychonaut as his employment at DOW actually sanctioned such exploration, at least while he was working there. His work following his parting with DOW is not sanctioned nor controlled, and can only be taken as subjective interpretation in a non-experimental setting. Few psychoactives have been fully explored in an experimental setting and thus, the pure (not sure if that is the right word, perhaps ideal?) psychonaut is a rare one. In terms of maintaining objectivity in the face of exploration- a necessary trait for any respectable psychonaut- Shulgin does a fine job, but in an ideal world one would not have to settle for 'fine'.

I would say as a general rule of thumb as control in an experiment goes down, the rogue element increases. Now, I use rogue the adjective here, not the noun. I mean not to call Alexander Shulgin a rogue, but rather his actions are in some sense (particularly later in his explorations, though in some sense throughout) unorthodox and unpredictable, independant, rouge, acting outside of the desirable controls.

Could I please enquire as to your background in this area? You have a degree in pharmacology, or a related area, I presume?

I am well into the process (about 9 months away) of completing a degree in Neuroscience with a minor in Pharmacology. I have worked on several published research studies, including an MDMA-PTSD treatment Phase II trial.

[Synesthesiac]

Originally Posted by Shampoo

I have worked on several published research studies, including an MDMA-PTSD treatment Phase II trial.

I would be fascinated in the progress of these trials, and would presume you would be about the best person to ask. I have a few personal demons in my past, and although almost definately not suffering from PTSD, I'm sure some MDMA therapy could relieve some of the emotions invoked by the fiendish flashbacks I sometimes get. Can I enroll for the trials? *sarcasm intended (though I would love to!)

Withthout wanting to start hijack this thread, have you started any threads about the progress of these studies? I'm presuming that they are the studies funded by MAPS. If you could post any of the main interesting findings from the Phase I, and Phase II clinical trials then that would be most appreciated. And your opinions on what the likely outcome of the next trials will be would be great, along with what other implications MDMA may have on any other sort of psychotherapy treatments in the future, and how it will likely be recieved by the scientific community / psychotherapists / polotians / media / public. I find this whole area fascinating and would love to catch up with recent developments in MDMA's various clinical efficacies. Links to the recent studies (published or not) would be great too.

From what I've heard its proving pretty damn successful. Though this is based more on pop-sci media articles than published papers.

[Euphoric]

Can we get references for your data please shampoo?

[Shampoo]

Originally Posted by Euphoric

Can we get references for your data please shampoo?

.....

Originally Posted by Shampoo

unmonitored human trials have taken place under non-experimental conditions

So basically, no.

Most of the values are based on either anecdotal reports or intrinsic activity values from this paper:

Molecular interaction of serotonin 5 HT2A receptor residues Phe339(6.51) and Phe340(6.52) with super-potent N-benzyl phenethylamine agonists
Braden MR, Parrish JC, Naylor JC, Nichols DE
Mol. Pharmacol., 2006

There is no published, substantiated human data on this chemical. Any information that is out there is either anecdotal or speculative. If it is speculative, it is based on intrinsic activity values and comparisons to other n-benzyl derivatives.

Reputation Comments on this post:

	Thanks for the data in this thread.
	Thank you for this reference.

[RaverHippie]

I am not at all familiar with protocol but I bet there is some sort of guideline about not revealing results of an unpublished trial

I say this with the same interest in what Shampoo has to say as you Synethesiac

[fnord]

Great info on its activity shampoo,thanks you may have just saved grandma from wasting alot of money on something not so interesting. Is 25I-NBOMe predicted to have effects?

[Shampoo]

Originally Posted by fnord

Is 25I-NBOMe predicted to have effects?

This compound is also predicted to have no effects when administered orally (potentially due to high lipophilicity).

It's intrinsic activity (phosphoinositide [IP3] release assay) at 5-HT-2A receptors is 78% (compared to DOI: 77%)- though this is not always the best measure of psychedelic activity, as we have seen with many other compounds.

It's activity via parenteral routes is in accordance with its Ki for 5-HT-2A (i.e. very, very potent), active at 300µg or less, full +++ experiences at 500-700µg, symptoms of overdose at 2mg.

Massive variance has also been reported. Some reports of no activity at 4mg intranasal, and others of full +++ activity at 400µg via the same route from the same batch.

Please take note of this in the earlier post

Originally Posted by Shampoo

These are tools for probing receptor activity, specifically and only 5-HT-2A/sometimesC receptors. They bind with an unbelievable affinity to these receptors and are thus very useful in research, not on blotters. Stay away from these chemicals. They are not formally tested in humans in any published document (not even rogue psychonaut publishing a la Alexander Shulgin), and may have long lasting, intense effects that may not be pleasant. Enzyme assays have yet to be done either, and we have no idea what the natural byproducts of the enzymatic degradation of these compounds are: for all we know (though unlikely), the compounds resulting from 25I-NBOH degradation could be potent neurotoxins.

I would say stay away from these ones until more is known, but if you or your friends decide to dive in, document everything, if nothing else than for the enrichment of human knowledge.

But seriously, leave the hyperpotent receptor agonists to the neuroscientists/neuropharmacologists. These are- in so many words- not to be 'played' with.

For more information, see "Molecular Interaction of Serotonin 5-HT2A Receptor Residues Phe339 and Phe340 with Superpotent N-Benzyl Phenethylamine Agonists" - Braden et al. 2006.

Reputation Comments on this post:

	More usefull data. Thanks.
	Great info, detail and even a citation. Quality post.
	excellent contributions to, and expansion of knowledge in thread.

[slownerveaction]

Nichols stopped aiming to produce 5-HT agonists with pleasant/psychedelic effects some time ago, namely after the publication of the (in)famous pihkal and Shulgin's subsequent treat, tihkal.

That strikes me as untrue. He published a review in 2004, PMID 14761703, and the abstract reads thusly:

Hallucinogens (psychedelics) are psychoactive substances that powerfully alter perception, mood, and a host of cognitive processes. They are considered physiologically safe and do not produce dependence or addiction. Their origin predates written history, and they were employed by early cultures in a variety of sociocultural and ritual contexts. In the 1950s, after the virtually contemporaneous discovery of both serotonin (5-HT) and lysergic acid diethylamide (LSD-25), early brain research focused intensely on the possibility that LSD or other hallucinogens had a serotonergic basis of action and reinforced the idea that 5-HT was an important neurotransmitter in brain. These ideas were eventually proven, and today it is believed that hallucinogens stimulate 5-HT(2A) receptors, especially those expressed on neocortical pyramidal cells. Activation of 5-HT(2A) receptors also leads to increased cortical glutamate levels presumably by a presynaptic receptor-mediated release from thalamic afferents. These findings have led to comparisons of the effects of classical hallucinogens with certain aspects of acute psychosis and to a focus on thalamocortical interactions as key to understanding both the action of these substances and the neuroanatomical sites involved in altered states of consciousness (ASC). In vivo brain imaging in humans using [(18)F]fluorodeoxyglucose has shown that hallucinogens increase prefrontal cortical metabolism, and correlations have been developed between activity in specific brain areas and psychological elements of the ASC produced by hallucinogens. The 5-HT(2A) receptor clearly plays an essential role in cognitive processing, including working memory, and ligands for this receptor may be extremely useful tools for future cognitive neuroscience research. In addition, it appears entirely possible that utility may still emerge for the use of hallucinogens in treating alcoholism, substance abuse, and certain psychiatric disorders.

That seemed pretty supportive to me, but maybe I'm just overoptimistic. In addition, in his 2006 paper in J. Med. Chem. where he identified the brominated benzocyclobutane, PMID 16970404, he does a treated-water replacement test with LSD and something else and it compete nanogram-per-nanogram with LSD. So he's at least asking the questions in some way if not tasting them himself, as his old mentor did.

[Synesthesiac]

While I dont think that Nichols is anti-drug in any way I dont think that he wants the sort of negative attention and press that Shulgin has had heaped on him for all the chemicals that he's created. I think that Shulgin is a great (yet often misunderstood) scientist, who, although has not always followed what is considered the *respectable* scientific method of documenting his discoveries, is never the less still a great guy. But by creating these chemicals this gives people who are complete irresponsible idiots with drug use a person to blambe when something goes terribly wrong. Even some of the drug fatalities that have happened over the years get blambed on Shulgin by overtly capricious people. I think that this is what Nichols wants to avoid.

[terrapinzflyer]

I have added an experiences page

Hopefully an intelligent labrat can stumble in and give swim & swiy some first hand experience one of these days.