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Positional isomers of 4-FA and 4-FMA

Coolio

Coolio

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Feb 29, 2004
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What if anything has been studied on the changes that moving the fluorine from the 4- position to 1,2,3, and 5 positions bring with the positional isomers of 4-fluoroamphetamine and 4-fluoro-N-methylamphetamine?
 
Well 2-FA, 3-FA, and 2-FMA already exist. I do not believe that 1-FA or 5-FA have been synthesized. In fact the only 5-fluorinated amphetamine I'm finding any information on is 2,4-dimethoxy-N,N-dimethyl-5-fluoroamphetamine (from PiHKAL's 2,4-DMA entry). You may be interested in obtaining several articles from Journal of Fluorine Chemistry, specifically "Fluorine substituent effects (on bioactivity)" from issue 109 and "Important fluorinated drugs in experimental and clinical use" from issue 118, and maybe "Relationship between the Serotonergic Activity and Reinforcing Effects of a Series of Amphetamine Analogs" too. I don't have any access to the full content of these so I apologize for not being able to help you out.

you may also be interested in "Isomeric Fluoro-methoxy-phenylalkylamines: a new series of controlled-substance analogues (designer drugs)", which focuses more on the chemistry (GC/MS, etc.) than bioactivity, and which again I apologize for not having access to.
 
ebola? said:
1-FA cannot exist, as The 1-position on the ring is where the propylamine attaches.

ebola
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I assumed that he was treating the propylamine as the 6-position as that is the only one he did not specifically mention.

And now that I think of it, 4-FA 3-FA and 2-FA are the only ones that can possibly exist; because of the "ring flipping" thing associated with phenethylamines, (R)-2-FA is the same as (S)-5-FA (and vice versa), and (R)-3-FA is the same as (S)-6-FA (and vice versa).
 
^ Not quite. 2-FA = 6-FA and 3-FA = 5-FA. There's no need to complicate it further by taking the R/S stereochemistry into account, as there is free rotation around the phenylalkyl C-C bond, and the only chiral centre is the alpha carbon. "Ring flipping" is a term that can be correctly applied to cyclohexane type structures, but not to aromatic structures.
 
I assumed that he was treating the propylamine as the 6-position as that is the only one he did not specifically mention.
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A safe assumption, but does that choice of nomenclature fit with the 4,3, and 2 ring-substituted compounds, as commonly reported?

edit: I later acted as a competent human with access to Google. Numbering with the position of the ethylamine substitution as 6 does not allow for 2cb as we know it to have a methoxy substitution at 5, nor does it allow for MDMA as we know it to have a 3,4-methylene dioxy substitution, to take two examples. Let's stick to the usual numbering to avoid confusion. The 5 and 6 position fluorine substitutions are the unexplored ones.

ebola
 
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Sounds like a mission for scifinder

I believe most of these have all already been discussed here and are active stimulants
 
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