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3-pseudotropyl 4-fluorobenzoate freebase?

Just say yes...

i put a lot of years behind the bench. Made over 2000 new compounds, lots of patents,papers, all that rot.That's why i get peezed off when we can't discuss synthesis:! .
Alot of the questions asked here could easily be dealt up an answer in no time with sci-finder, GAD, i miss it.
 
THis is also why "Fluorinated water" doesn't kill us; it's because Fluorine salts are used, that is the toxic F2 gas is not present only F- (with it's positive salt counterion) being the source of "fluorine", in this case called a"fluoride".
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As vecktor has pointed out, fluoride ions are toxic and if kids eat toothpaste (weird little fuckers that they are) it's a trip to A&E/ER because fluoride acts as an inhibitor of oxidative phosphorylation in red blood cells the way cyanide ions do in most other cells.

I know there must be the odd (very odd) adult who eats toothpaste, but as a rule, toothpaste/fluoride toxicity admissions to hospital nearly always involve rugrats
 
hussness said:
I ate toothpaste for the first 18-20 years of my life. Maybe that's why I'm so screwed up! ;)
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how did you manage to quit? did you cold turkey or did you taper or did you substitute cheese spread or something for it :)
 
Next time maybe you should get a slightly safer substitution at the 4 position? I'm assuming you had this custom synthed.
 
otb01 said:
Next time maybe you should get a slightly safer substitution at the 4 position? I'm assuming you had this custom synthed.
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eh???

did you read the thread?

fluorine does not fall of p-fluorobenzoic acid and p-fluorobenzoic acid is not toxic.


there is some suggestion that the pseudotropyl benzoates have 5ht activity of some sort
Pseudotropyl halogeno-benzoates and their use in migraine treatment

United States Patent 4486441

http://www.freepatentsonline.com/4486441.html

will have to read it properly then post

I was unaware that pseudotropine has exo configuration, ie 3 beta tropanol, for some reason I had thought that tropine was the exo ie conforming to cocaine configuration. Apparently not. so pseudotropinyl esters do not correspond to the benztropines, which have the same configuration as the anticholinergcs
 
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I did read the thread but I'm saying to prevent future misconceptions, a safer sub might have been beneficial.
 
Safer sub? What would that be? Changing the substituent will also change characteristics of the molecule (affinities, physiochemical, etc.). Fluorine as a substituent is pretty common among pharmaceuticals, so there's definitely not a rule that says "fluorine as a substituent is always toxic/more harmful". It is something that depends...
 
ring subsituted-fluoro-tyrosines/phenylalanine amino acids are known to be toxic to bacteria (and most likely higher organisms) because they are catabolized down to the fluoroacetates, which are not so good for the krebs cycle. tyrosine levels are highly regulated in the cell and any excess is catabolized rapidly.

of course, the compound in question isn't a tyrosine analogue and i won't say aromatic fluoro compounds are inherently safe or dangerous, but they are well known in medicinal chemistry...

just don't let em sap and impurify your precious bodily fluids
 
ring subsituted-fluoro-tyrosines/phenylalanine amino acids are known to be toxic to bacteria (and most likely higher organisms) because they are catabolized down to the fluoroacetates, which are not so good for the krebs cycle. tyrosine levels are highly regulated in the cell and any excess is catabolized rapidly
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How do bacteria get from a ring substituted fluoro compound to fluoroacetate? That involves taking the fluorine off the aromatic ring and sticking it on a 2 carbon chain?

I'd be pretty confident in saying that mammals don't possess the machinery to do things like that (and fluoroacetate isn't equally toxic to all mammals. Some of the weird marsupial fuckers in Australia can eat native plants with level of fluoroacetate that kill anything else with a total indifference)
 
^
m-Fluorotyrosine convulsions and mortality: relationship to catecholamine and citrate metabolism.

1967 Journal of Pharmacology and Experimental Therapeutics

ABSTRACT
WEISSMAN, ALBERT AND B. KENNETH KOE. m-Fluorotyrosine convulsions and mortality:
Relationship to catecholamine and citrate metabolism. J. Pharmac. exp. Ther. 155: 135-144,
1967. The characteristic convulsions and mortality induced by DL-m-fluorotyrosine (m-FT),
in mice were antagonized by anticonvulsant drugs, but not by high doses of chlorproma-
zinc, atropine, lysergic acid diethylamide or several drugs variously affecting catecholamine
metabolism or storage. Sublethal doses of m-FT were slightly potentiated by ce-methyltyro-
sine and by catecholamine depletors, but these effects were marginal and a variety of other
centrally acting drugs was ineffective in potentiating m-FT. Despite the structural simi-
larity of rn-FT to several potent tyrosine hydroxylase inhibitors, rn-FT was essentially in-
active as a tyrosine hydroxylase inhibitor in vitro ; similarly, rn-FT only slightly reduced
norepinephrine concentrations in mouse brain. rn-FT did, however, cause pronounced ac-
cumulation of citric acid in mouse kidney and brain. It is postulated that the convuLsions
and mortality caused by rn-FT are primarily unrelated to catecholamine metabolism, but
are instead the result of metabolism of rn-FT through tyrosine pathways to fluoroacetate.
Supporting evidence was provided by a study of o-, rn- and p-fiuorophenylalanine ; only
the m isomer was lethal at low doses, and only this compound caused citric acid accumula-
tion. The speculative explanation that rn-FT is toxic by being metabolized to fluoroacetate
does not, however, explain why in mice rn-FT has more convulsant properties and is more
toxic than fluoroacetate, its proposed active metabolite; drug penetration factors may ac-
count for these discrepancies.

Tyrcatab.gif


now just imagine a meta-fluoro group

ps-look at the compounds they just got to play with !!! the good ole days :)
 
para rather than meta fluoro will block the pathway, as I think the ring opening of a lot of benzene compounds proceeds through a ring epoxy intermediate. f it cant form the epoxy then it can't open. if it is a quinone pathway then fluoro will block that too.
with fluorotropacocaine the primary metabolic path is going to be esterase cleavage of the fluorobenzoic acid, which is not toxic to any significant degree and
pseudotropine which is mildly toxic.
Supporting evidence was provided by a study of o-, rn- and p-fluorophenylalanine ; only the m isomer was lethal at low doses, and only this compound caused citric acid accumulation.
Click to expand...
 
most of the phenyl degradation goes through funky intermediates using metalloenzymes, i can't remember an epoxy though...most is quinones and radicals derived with the alpha-keto-glutarate dependent enzymes

but yea, only the meta would be bad as they say, so fergit aboot it
 
Isn't tyrosine..........

...conserved by the body to become meta-hydroxylated to L-Dopa, then decarboxylated to dopamine in the brain rather than first deaminated?
 
Since there is only a single ester-linkage, the duration of action of this drug should be longer, but if you remove the ester totally and make the C-C bonded version, then it would be very long-lived indeed. I seem to remember that the C-C bond of p-F cocaine has a duration of 11 hours or so; Off 1 line! It would also be possible to take orally, so voila, cokeadone. Rather than short highs followed by long lows of cocaine, a daily dose of 'juice' would allow people to get off the 'ritual de lo habitual' of snorting/snorting/shooting.
 
I am interested.

Does anyone else happen to have subjective experience with this stuff?

Also, slopoke - how would you describe the effects? And perhaps more importantly, the after-effects?
 
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