• Neuroscience & Pharmacology Discussion Welcome Guest
    Posting Rules Bluelight Rules
    Recent Journal Articles Chemistry Mega-Thread
    FREE Chemistry Databases! Self-Education Guide

  • N&PD Moderators: Skorpio

Why are there no substituted 3,5 phenethylamines?

B

bloodshed344

Bluelighter
Joined
May 9, 2012
Messages
1,575
Besides the ones with an oxygen at the 4 position, like escaline.

Why is there no 2C-B with the 2 dimethoxy instead at the 3 position, for example? Is the chemistry impossible?
 
Synthesis discussion is not allowed here, but the chemistry leading to 4-substituted-3,5-dimethoxyphenethylamines, while not impossible, is much more challenging than the 2,5-series. Shulgin did make 4-alkylthio-3,5-dimethoxyphenethylamines in Pihkal.
 
PiHKAL DESOXY said:
A mescaline analogue with a bromo atom in place of the 4-methoxyl group is an analogue of mescaline in exactly the same way that DOB (a very potent am-phetamine) is an analog of TMA-2 (the original trisubstituted amphetamine). This analogue, 3,5-dimethoxy-4-bromoamphetamine, has been found to be a most effective serotonin agonist, and it is a possibility that it could be a most potent phenethylamine. But, as of the present time, it has never been assayed in man.
Click to expand...

I think they've been made, but Shulgin decided his time was better spent assaying the more potent 2c- series.

As pointed out above, synthesis of 3,4,5 substitution pattern is much harder to achieve than 2,4,5. - because the "core" for 2,5 substitution is easily availiable, but 3,5 pattern must be constructed manually usign a route that takes many more steps...
 
Ann Shulgin had a several day long major freakout / 'spiritual crisis' after taking 3,5-dimethoxy-4-methylphenylethylamine, but PiHKAL goes on to claim it is inactive. She actually got as high as the Atman.
 
I should have said, "Inactive as a substance likely to produce a long-lasting spiritual crises," although that is exactly what happened to Ann the first time she took it. Anyway, the spiritual crises chapter of PiHKAL is one of its best in my opinion.

Back on topic, 4-bromo-3,5-dimethoxyamphetamine was assayed in the low mg range and found to be, "Definitely not a placebo." It apparently wasn't studied too much more though.

Personally, I have always wanted to have more information on 3,5-dimethoxy-4-(n)-pentylphenethanamine. Its synthesis is not prohibitively difficult.
 
Last edited:
I don't think so. Well, maybe a long time ago somewhere but not that we know of.
 
If Cl is a bioisostere to OMe, I imagine 3,5-dimethoxy-4-chlorophenethylamine & 3,4-dimethoxy-5-chlorophenethylamine would be interesting as mescaline isomers, and presumably the same potency.

Searches only pull up 2C-C
 
You must log in or register to reply here.
Top