Bromoline / 3,4,5-MBM

[Nexus_Tripper]

Bromoscaline / 3,4,5-MBM

3,5-dimethoxy-4-bromophenethylamine. Does anyone know anything about this one?

 

[Dawglaw]

If it has the word bro in it, you know its good!

 

[perpetualdawn]

broscaline?

 

[Torresmo]

like a day spent with your bro on mescaline?

 

[tryp2fun]

Actually, Dave Nichols made this compound back in 1977.

J Med Chem. 1977 Feb;20(2):299-301.
Lipophilicity and serotonin agonist activity in a series of 4-substituted mescaline analogues.
Nichols DE, Dyer DC.
Abstract
Replacement of the 4-methoxy of mescaline with higher alkyl homologues or with bromine led to increased activity at serotonin receptors in a sheep umbilical artery preparation. This activity appears correlated with lipophilicity, as measured by 1-octanol-water partition coefficients, but drops off when the 4-substituent is about five atoms in length. It is suggested that 3,4,5-trisubstitution may give compounds which are as active as the 2,4,5-substitution pattern.

4-Bromo-3,5-dimethoxyphenethylamine was the most potent serotonin agonist in this paper, 7.6 times as potent as mescaline.

 

[perpetualdawn]

That's really interesting thanks for digging that up tryp2fun. I suppose there aren't any know human ingestions of this compound eh? 7.6 times as potent as mescaline brings it into the realm of maybe being worth synthesizing (price wise).

edit: It looks like this has a name collision with an enzyme called bromoline. I guess that means we better start calling it broscaline Fits the pattern of escaline, proscaline, allylescaline etc...

 

[nickfurry]

2,5-dimethoxy-4-bromophenethylamines before 2,5-dimethoxy-4-hydroxyphenethylamines!

 

[Incunabula]

I lol'd at the first few posts :D But seriously, I don't understand were the name bromoline comes from? 3,4,5-MBM isn't half bad, I guess. But Broscaline? I vote for Bromoscaline. You have to consider what you'd call the same compound with chloro on the 4-position, for instance, chloskaline or Chloroscaline? Most certainly the later, if you ask me. And Broscaline is just too silly. Not that it's up to us to decide, anyway.

All the mescaline analogs we've seen so far haven't really been that great, but I'd rather try this as a legal 2CB alternative, than bk-2CB. That shit sounds like a waste of time,imo, compared to the real 2C's.


2,4-dimethoxy-4-hydroxy-phenetylamines? nick. What do you mean?

 

[Solipsis]

Bro's be4-HO's :D

(by the way, DOB is also called 'brolamfetamine' )

 

[Incunabula]

Bro's be4-HO's :D

(by the way, DOB is also called 'brolamfetamine' )

Ha ha :D now I got it........lol

Didn't know that about DOB, I wonder were the L comes from?

"Hey, bro. Want some Bro-lame-fetamine?" Lol :D

 

[Goddess Mode]

Bro's be4-HO's :D

This is the first post that made me literally laugh out loud in quite a while. xD

Funny, I was just looking for info about this compound the other day, didn't know it had already been made. 3,5-DMPEAs being potentially as potent as 2,5-DMPEAs sure sounds intriguing....

 

[Incunabula]

It does, but remember, there was a reason Shulgin chose to focus on the 2,4,5-pattern, and not the 3,4,5-pattern.

 

[yaesutom]

I would try it if it became available, I like the 3,4,5 pattern (I like methallylescaline and mescaline).

 

[Solipsis]

It does, but remember, there was a reason Shulgin chose to focus on the 2,4,5-pattern, and not the 3,4,5-pattern.

IIRC he had the insight because of the TMA's:
http://en.wikipedia.org/wiki/Trimethoxyamphetamine#Properties

It is suggested that this substitution pattern leads to compounds which are intrinsically at least as active as compounds with 2,4,5-trisubstitution. The report3 that 2,4,5-trisubstitution gives compounds of highest activity may simply reflect the fact that 3,4,5-substituted compounds of comparable log P had not been examined.

http://bitnest.ca/Silo42/10.1021/jm00212a022.pdf

No idea where that L came from... bromolomo?

 

[Goddess Mode]

Shot in the dark: R-DOB = bro-L-amfetamine ?

It does, but remember, there was a reason Shulgin chose to focus on the 2,4,5-pattern, and not the 3,4,5-pattern.

Yeah, like Solipsis said the TMAs right? Methoxy groups don't always seem to be the best for testing the potential of a phenethylamine pattern though.... I think he tried the amphetamine version of this too didn't he? But the only phenethylamine one I recall that would be analogous to a 2C-x would be DESOXY to 2C-D.... I at least definitely think it's a little early to judge the whole class, there could still be some gems hidden in there!

 

[Incunabula]

Yeah, it was because of the TMA's, that's what I meant

I do agree that there's bound to be some gems among the compounds with that pattern, there must be. And I'd certainly be keen to try bromoscaline if it became available. A halogen on the 4-position is bound to be a completely different thing than escaline, proscaline, or AL or MAL.

 

[Dresden]

To the OP:

Is this molecule available now (or about to be) commercially or are you just coming up with new ideas? If the case is the latter, topics like this one go into the sticky "I like to draw pictures of random molecules" thread over in the advanced psychopharmacology forum.

 

[benzo_rabbit]

I vote for bromoscaline. Can anybody tell me why it's the 4 position that has been substituted instead of the 3 or 5 positions in the most commonly available mescaline analogues?

 

[Incunabula]

I vote for bromoscaline. Can anybody tell me why it's the 4 position that has been substituted instead of the 3 or 5 positions in the most commonly available mescaline analogues?

Because Shulgin found out, by trial and error, that the 4-position on phenethylamines is were the magic happens
There are exceptions though, so it's not like you can't have a good phen with something other than a methoxy on the 5-position, for instance.

 

[Bagseed]

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?