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Bromoline / 3,4,5-MBM

I think Shulgin said that the 2,4,5's are easier to synthesize, something about it being easier to stick things on the 4 position. In these modern times though it seems like China would be capable of a bunch of new cheap 3,4,5's :).
 
Bagseed said:
I wonder why the substitutions on the mescaline analogues are always -oxy (methallyloxy, ethoxy,...). this one appears to be bromo, not "bromoxy". what's the reasoning behind this?
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The oxygen has been removed in this molecule. All mescaline analogs were previously 3,4,5 analogs of the 2C-O series. This is an analog of 2C-B.
 
What other drug could possibly be named Broscaline? BrO-scaline can't be made afaik, and if it was, I wouldn't want to try it... Besides, you don't say Methoxyscaline, do you?

Seriously folks, this is the best chance we've got of ever having a drug named Broscaline.

It totally is Broscaline.
 
well I mainly wonder what it has to do with SAR... i mean, why are the substitutions of the mescaline analogues ethoxy, allyloxy, propoxy, etc, whereas the 4-substitution on the 2C-X are methyl, ethyl, propyl, etc.?
 
According to Nichols' 1977 study in J Med Chem, Feb 20(2):299-301, the most active of the compounds tested was 3,5-dimethoxy-(n)-pentylphenylethylamine. That doesn't surprise me. I have been trying to persuade someone to bring that one to market for years, to no avail thus far.
 
It'd be interesting to see how this one plays out. Sounds promising on paper, and well... I mean... Broscaline. :p I'm intrigued, not only from the possibility of a compound being called Broscaline, also being 7.16 (So that'd put it roughly around Proscaline/Escaline potency) the potency of Mescaline, hopefully we can see this at some point.
 
Maybe we could call it meta-2C-B, since it's basically an isomer of 2C-B? (Methoxy groups at 3,5 instead of 2,5)

Or maybe a fun option, let's call it broscaline, and rename 2C-B to parabroscaline.
 
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I like the name, broscaline. 3,4,5-2C-B is my second choice. As for 3,5-dimethoxy-4-(n)-pentylphenethanamine.hcl, I like the name pentescaline.
 
Dresden said:
According to Nichols' 1977 study in J Med Chem, Feb 20(2):299-301, the most active of the compounds tested was 3,5-dimethoxy-(n)-pentylphenylethylamine. That doesn't surprise me. I have been trying to persuade someone to bring that one to market for years, to no avail thus far.
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There is no n-pentyl derivative in the paper. Nichols refers in this paper to the n-pentyl derivative in another paper, and that it is inactive. The longest alkyl chain in this paper is the n-butyl, and it has lower activity than any other derivative. The most active is the 4-bromo. Also, the longer alkyl chains tend to give antagonists rather than agonists. What looks interesting is the 4-benzyloxy derivative, which is about 3 times more potent than mescaline.
 
Oh ok.

What does Nichols say about the 4-methyl mescaline analogue? It is called DESOXY in PiHKAL, and Shulgin seemed to think it was inactive; however, his wife, Ann, apparently tripped really, really hard after taking it the first time.
 
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