3-pseudotropyl 4-fluorobenzoate freebase?

[slopoke]

I managed to get my hands on a sample of this compound, although it is the freebase, not HCL. I tried snorting it but it is VERY insoluble and just causes burning in the nose and you can feel the bits in the back of your throat.

Would i be able to smoke the freebase? I'm quite worried that the fluorine will break off and poison me!:D --

The reason it is base and not HCL is that in both acetone and ether recrystallization processes only 15% of solids would precipitate, meOH and aqHCL caused ester hydrolysis as well.

Anyone got any ideas on how to get a water soluble salt out of it? I hope this isn't too synth orientated but its on a par with crack -- coke discussions and you see them pretty often round these parts.

also, does anyone have an idea if this would form the equivalent of a cocaethylene type molecule when mixed with alcohol? I'm looking to minimise harm in these fairly uncharted waters!

 

[vecktor]

I managed to get my hands on a sample of this compound, although it is the freebase, not HCL. I tried snorting it but it is VERY insoluble and just causes burning in the nose and you can feel the bits in the back of your throat.

Would i be able to smoke the freebase? I'm quite worried that the fluorine will break off and poison me!:D --

The reason it is base and not HCL is that in both acetone and ether recrystallization processes only 15% of solids would precipitate, meOH and aqHCL caused ester hydrolysis as well.

Anyone got any ideas on how to get a water soluble salt out of it? I hope this isn't too synth orientated but its on a par with crack -- coke discussions and you see them pretty often round these parts.

also, does anyone have an idea if this would form the equivalent of a cocaethylene type molecule when mixed with alcohol? I'm looking to minimise harm in these fairly uncharted waters!

use an organic acid, citric or tartaric for example in dry MeOH. the acetate is probably doable too. you have to figure out the details, as this could easily cross the line.

I think it also hurts lots because it is not a very good local anaesthetic compared to cocaine.
there is no way you will get the fluorine off that molecule
it also is missing cocaines methoxycarbonyl group so it cannot transesterify to a cocaethylene type compound.
this compound is a big unknown all round so harm minimisation would be to put it in a vial and look at it and occassionally use it as a topic for conversation...

 

[slopoke]

Thanks, i'll see what i can do with that info.

vector, what do you think about smoking the freebase, would it be unwise? I know smoking freebase is unwise in general (more for reasons of addiction) but from a health viewpoint, are there any immediate dangers? I know F&B mentioned fluorine is unreactive once bonded due to electronegativity so i'm guessing that it should be ok?

 

[LuxEtVeritas]

other than than normal inherent issues smoking it should not otherwise be harmful


lacking the COOMe i believe alcohol will not have the same correlation as Cocaethylene to Cocaine

 

[slopoke]

Cheers, i'll maybe smoke a little bit tonight (famous last words, eh?).

 

[slopoke]

this compound is a big unknown all round so harm minimisation would be to put it in a vial and look at it and occassionally use it as a topic for conversation...

Like thats going to happen! I'll experiment shulgin style, don't worry! I'll worry about parkinsons at a later date

 

[ralf2]

Now that we're on the topic of this compound, does anyone perhaps have any litterature references on it? I have searched, but found nothing.

 

[slopoke]

I haven't seen anything while searching on it, other than what is on here. Its also known as 4-fluorotropococaine if thats any help to you.

 

[fastandbulbous]

Now that we're on the topic of this compound, does anyone perhaps have any litterature references on it? I have searched, but found nothing.

I got a ref. many years ago from 'The Alkaloids' - but don't ask where in that series etc as my memory of things that I read 20+ years ago is a bit patchy to say the least. Only thing I remember clearly was that it had an affinity for the DAT that indicated it'd be about 40% the activity of cocaine.

As for salt formation, just combine it with the equivalent molar amount of say tartaric acid so that on contact with moisture, the tartaric acid dissolves first, which instantly forms an ionic compound with the fluorotropacocaine & solublizes it (as a rule, tartrates are always soluble, along with acetates).

Other than that, it'll be a right fanny on making a salt because of things previously mentioned


BTW, in terms of activity, 8 out of 10 people who expressed a preference said their cokehads/coke fiends preferred it to street coke (OK it was just two regular coke users, but they preferred the pre compound to the street Peruvian marching powder they had on their person). For me, it did everything that coke does for/to me in shovelfuls... turned me into a grade a obnoxious twat, which means I can't see it becoming popular with me, but then again I generally have nothing to do with coke for the reason outline above (I actually take pleasure watching people's faces as I turn down free lines of coke when offered! )

 

[ralf2]

I got a ref. many years ago from 'The Alkaloids' - but don't ask where in that series etc as my memory of things that I read 20+ years ago is a bit patchy to say the least. Only thing I remember clearly was that it had an affinity for the DAT that indicated it'd be about 40% the activity of cocaine.

I actually went through the four reviews of tropane alkaloids in different volumes of The Alkaloids just a few days ago and didn't find any mention of it. But I might read it again, just to see if I might have missed it somehow.

I wish I had access to something else than just the printed version of beilstein (which also seems to end somewhere in the 60's-70's in my library)...

 

[Smyth]

It's trial and error mate. If the HCl salt is very insoluble, you'll just have to try experimenting with other acids of varying composition. Citric acid is a good choice because its known to be non-toxic and is readily available in the grovery store for cheap.

 

[Bondmaker]

Fluorine

Fluorine and a flourinated carbon compound are two very different beasts. When heating a fluorinated carbon compound, even if one were to break the fluorine carbon bond, the chances of forming any toxic amount of F2 (diatomic fluorine gas, the "toxic" form of fluorine) is nil. The fluorine atom attached to carbon atoms, is done to stabilize the molecule metabolically. Since "defluorination" is a difficult process, when fluorine is put on metabolially activated sites in a molecule , it lengthens the metabolic half- life of the molecule and is usually excreted with the fluorine atom still intact. 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". Same as Chlorine, Bromine and Iodine, however as we go downward in the periodic table of the "halogen" row, bonding gets weaker as electronegativity drops off and as the halogen carbon bond gets weaker, it is easier to metabolize.

 

[vecktor]

flouride ions are rather toxic, it is not just elemental fluorine. fluorinated water doesn't kill us because there is next to no fluoride (in the form of monofluorophasphate) in it.
with organic fluorine molecules the fluorine is tied up bound to carbon and it remains so then generally it isn't very toxic. however some organo fluorines are exceedingly toxic, one of the thermal breakdown products of teflon (PTFE) is perfluoroisobutene which is exceptionally toxic. another example is fluoroacetic acid. then again there are fluoroalkanes which can be used as blood replacements they are so non toxic and they have been used to enable underwater breathing of liquids like in the film the abyss... so it is impossible to genralise about the toxicity of organic molecules containing fluorine or even fluorine in general.

the p-fluoro tropococaine in this thread is not going to lose the F. As for smoking it the Boiling point is critical and I would expect it to be lower than that of cocaine.

the related tropacocaine is a well known substance which was used in opthalmic surgery IIRC though I do not know if it is still used. the related tropine ester (rather than pseudotropine) is a quite potent anticholinergic substance. the substance where the benzyl is replaced with a diphenylether is benztropine an anticholinergic with dat activity, and the benztropine with a parafluoro on each of the phenyl rings is a potent dat inhibitor though it doesn't interact at the cocaine site.

p-fluorotropacocaine is mentioned in singhs review of cocaine analogs with little data. what is interesting is that p-fluorotropacocaine has the wrong stereochemistry compared to cocaine yet is still effective. I am williing to predict that the 3,4 dichlorobenzoic acid ester of pseudotropine is more potent than the p-fluoro, as the 34 dichloro in low affinity DAT inhibitors is very effective in increasing potency, and is sufficient to overcome the 'wrong' sterochemistry.

 

[slopoke]

Well, i tried smoking a tiny amount last night, to see if i could potetially work up the dose.... BLEUGH! It is the most horrible, chemical, acrid smoke imaginable. Just hitting the back of my throat nearly ripped it out.

Going to have to work on getting a salt form.

Any ideas if eating it will make the freebase usable? I've still got bits of the freebase in my nose from attempting to snort it yesterday afternoon, yummy.

 

[vecktor]

Well, i tried smoking a tiny amount last night, to see if i could potetially work up the dose.... BLEUGH! It is the most horrible, chemical, acrid smoke imaginable. Just hitting the back of my throat nearly ripped it out.

Going to have to work on getting a salt form.

Any ideas if eating it will make the freebase usable? I've still got bits of the freebase in my nose from attempting to snort it yesterday afternoon, yummy.

dissolve the freebase in citric acid acetic acid or any other non toxic acid and then drink, easy.
I would not recommend consuming the freebase directly as it is a pretty strong basic material.

 

[Bondmaker]

All freebases..

taken orally, and all salts of any acid become hydrochloride salts when they hit the stomach. A few mg of a freebase would not "basify" the gut, remember you have two chew at least 2 grams of calcium carbonate in the form of "tums" to help an acidic stomach. There is such a high concentration of HCl in the stomach that any salt just dissociates from it's counterion and becomes the hydrochloride salt.

 

[vecktor]

taken orally, and all salts of any acid become hydrochloride salts when they hit the stomach. A few mg of a freebase would not "basify" the gut, remember you have two chew at least 2 grams of calcium carbonate in the form of "tums" to help an acidic stomach. There is such a high concentration of HCl in the stomach that any salt just dissociates from it's counterion and becomes the hydrochloride salt.

yes but you have to get it to the stomach first....think about it,
ammonia will react with hydrochloric acid in the stomach to make neutral ammonium chloride but on the way it will severely corrode the mouth and oesophagus..

there are several good sources of data on salt formation, this one is aimed at the process chemist but is very interesting,
http://kilomentor.chemicalblogs.com...l_salts_for_chemical_process_development.html

 

[Bondmaker]

even chewing..

10 or so mg of compound as the freebase can leave a yucky taste in your mouth, but so will the salt.
Why say a fumarate salt or a maleate salt or etc, etc is made in a pharmacetical prep is to get a perfect salt to compound ratio. We had a compound destined for the clinic that made a consistently variable hydrochloride salt. The FDA would not ever accept this. The compound was dibasic with one very weak basic site. When the fumarate was prepared, we were able to get a consistent hemifumarate crystal structure, and thus an acceptable salt for FDA approval.

 

[Smyth]

*We* had a compound destined for the clinic that made a consistently variable hydrochloride salt. The FDA would not ever accept this. The compound was dibasic with one very weak basic site. When the fumarate was prepared, *we* were able to get a consistent hemifumarate crystal structure, and thus an acceptable salt for FDA approval.

Bondmaker, are you saying you have worked as a professional in the pharmaceutical industry? Please explain..

 

[vecktor]

Bondmaker, are you saying you have worked as a professional in the pharmaceutical industry? Please explain..

I would expect that a few readers and posters of ADD have in the past or are still working in the pharma industry.

can anyone get the toxicity information for tropidine, as this would be formed during smoking of p-fluoro tropacocaine. I remember both tropine and pseudotropine as being poisons, they are skull and crossbones on the containers, I wonder about tropidine.