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DOC-NBOMe HCL

stonerish

stonerish

Bluelighter
Joined
Jul 13, 2010
Messages
134
That is:

[2-(4-Chloro-2,5-dimethoxy-phenyl)-1-methyl-ethyl]-(2-methoxy-benzyl)-amine hydrochloride


Any thoughts? Relative shots at potency, general nature, anything really...
 
when one considers that NBOMe-2C-C is about 100 times more potent than 2C-C, then an educated guess would be that NBOMe-DOC could be active in the 10 microgram range. that is only speculation, of course, but it still gets my imagination going. even think of its dragonfly analogue, or what happens if you conformally restrict it (a la TCB-2), or if you replace the chloro by a trifluoromethyl group... sorry, my fantasy goes trough with me.
 
ungelesene_bettlek said:
when one considers that NBOMe-2C-C is about 100 times more potent than 2C-C, then an educated guess would be that NBOMe-DOC could be active in the 10 microgram range.
Click to expand...


Maybe this is the chem Nichols was talking about in the recent news story focused on him.
 
Its probably inactive.
NBOMe-2C-I is active but the DOI version is not and I would expect it so behave in the same way.
 
ungelesene_bettlek said:
when one considers that NBOMe-2C-C is about 100 times more potent than 2C-C, then an educated guess would be that NBOMe-DOC could be active in the 10 microgram range. that is only speculation, of course, but it still gets my imagination going. even think of its dragonfly analogue, or what happens if you conformally restrict it (a la TCB-2), or if you replace the chloro by a trifluoromethyl group... sorry, my fantasy goes trough with me.
Click to expand...

All work thus far shows that PEA SARs don't follow thru to their NBOMe counterparts.
 
According to Erny: "NBOMe amphetamines are about ten times weaker than their phenylethylamine counterparts."
Click to expand...

Correct. Also, yay!...we'll have a compound that's sufficiently weak to avoid the unwieldy task of measuring in the low single milligram to microgram range. Ideas on subjective effects?

ebola
 
You'll get more out of it by hydrolyzing the amine, as it is it's probably not very active, I'd guess 3-10mg would be an active dose. I'd be cautious, as always, though.

The better one which is probably orally active is gotten by methylating the alpha position on the non-phenethylamine moiety...
 
my gut tells me that this very well could just convert to "plain old" DOC in vivo but honestly i'm a moron when it comes to this stuff so that's just pure intuition...
 
It seems that extending the effective length and bulk of the NBOMe phenethylamines (and vastly more so the alpha-methyl homologs leaves relatively little room for increased bulk where the 4-position action is, if a chloro functional group is present and fully active, but that podgy bugger of an iodine is inactive, or at least, not active at any dose yet tested properly.

IIRC the NBOMe homolog of 2C-H is actually active, although I may recall reading that at least one person found it unpleasant, its just something lurking in the back of my mind though, I may be mistaken there, but it is definately reported active. As such, I have a distinct feeling that a 3-trifluoromethyl derivative would be if not inactive, the increased bulk would make the activity threshhold take a rather significant dive.

As for the dragonflies, well if the SAR holds through for the conformationally restricted dragonflies, or phenethylamines, and for that matter the hemi-fly compounds, both the fully rigid, much more planar, and likely more potent than the non-aromatic derivatives.

I would be interested to see what effect bulk at the 2, and 5-positions has, and what may come of an NBOMe-phenethylamine tweetio. Perchance careful study could yield some valuable information as to the deepest bowels and structure of the 5HT2a receptor.

Is there a better model of the 5HT2a receptor available now that is closer to being accurate than rhodopsin or beta-adrenoreceptor crystal structure?
 
NBOMe-2CI is active, just slightly less potent than NBOMe-2CC. Even NBOMe-2CCF3 showed reasonable activity in vitro though no human trials seem to have been reported. And NBOH-2CT7 was said to be active though again slightly reduced in potency. So there is still a reasonable amount of bulk tolerance at the 4-position, though apparently less than in the regular phenethylamine or amphetamine derivatives.

NBOMe-2CB-Fly is a known compound and has very high binding affinity at 5HT2A, though seems to be a fairly weak partial agonist. Again only in vitro studies have been reported though. Looking at the binding and activity of a tweetio like NBOMe-2CT2-5EtO, or a 3,4 disubstituted derivative like NBOMe-2CG5, would be very interesting for assessing how much further the N-benzyl derivatives are pushed into the binding site, and what effect this has.

And as nuke notes, alpha methylation of the phenethyl portion dramatically reduces both affinity and efficacy, so NBOMe-DOC will be weak at best. But alpha methylation of the benzyl portion seems to retain activity, though again only in vitro results are known.
 
mad_scientist said:
NBOMe-2CB-Fly is a known compound and has very high binding affinity at 5HT2A, though seems to be a fairly weak partial agonist.
Click to expand...

Could you mention what study you are thinking of that showed it to be a weak partial agonist?

Someone pointed out to me that there were variations in the efficacy results depending on the assay and Lab, and I am trying to compile the various published data on this compound you mentioned.

It seems as though the efficacy is dependent on whether the ex vivo rat tissue or in vitro human ectopically expressed receptor model systems are used. Do you know what system the NBOMe-2CB-Fly study(s) your referring to used? I am guessing from Heim (which used rat tissue)?
 
Yeah from the Heim thesis, and while the Silva thesis and that early paper by Elz et al report the same result, Vecktor is correct in pointing out that all three sources are published by the same group and so quite likely could have used the same data.

The more recent paper by Ettrup et al showed NBOMe-2CB-Fly to be a close to full agonist but it still had lower efficacy than NBOMe-2CI, NBOMe-2CC etc which were compared alongside, so I'm thinking they used a different assay and still found the same trend as the earlier publications.
 
5mg [2-(4-Chloro-2,5-dimethoxy-phenyl)-1-methyl-ethyl]-(2-methoxy-benzyl)-amine hydrochloride dissolved in distilled water. 1mg/1ml sol’n.

Starting 200mcg insuff.

For Science!
 
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And as nuke notes, alpha methylation of the phenethyl portion dramatically reduces both affinity and efficacy, so NBOMe-DOC will be weak at best.
Click to expand...

To reiterate, in this case, 'weak' might translate to "good recreational compound".

ebola
 
Its about time! When the time is right, you know. I Am determined to find out! Assuming the 1/10x DOx figure is true I will get there in good time, I intend to find out if no one else will before me, I'm working with what I got! Plan to confirm what can be, with what I have! Going shulgin style ofcourse, building my way there. Look forward to finding where this goes for me, for us!!! Will share ofcourse..!!

Comments? Anyone else, Anything?
<3
 
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