Author Topic: kitchen-tek cocaine analog? 3-psuedotropyl-ortho-hydrox/acetoxy-tropane  (Read 717 times)

Naphyrone

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kitchen-tek cocaine analog? 3-psuedotropyl-ortho-hydrox/acetoxy-tropane
« on: September 03, 2010, 10:37:40 AM »
this...could...be...awesome  ;D

http://en.wikipedia.org/wiki/Salicylmethylecgonine  < 10x in vitro ~3x stronger in mice than cocaine
http://en.wikipedia.org/wiki/3-%28p-Fluorobenzoyloxy%29tropane < 70% weaker

extraction and hydrolysis of atropine
extraction of tropine
Fischer-Speier esterification with 2-acetoxybenzoic acid or salicylic acid

end produkt :)
3-pseudotropyl-ortho-acetoxybenzoate / Salicyl-3-tropane

Seeing as this is such an amazingly simple compound to produce, hopefully it has good effects :)
I'm curious to see the difference in the one made with aspirin and the one made with salicylic acid and i'm really hoping that the ortho-hydroxy makes up for the potency compared to the 4-fluorotropacocaine.

NaBH4

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Re: kitchen-tek cocaine analog? 3-psuedotropyl-ortho-hydrox/acetoxy-tropane
« Reply #1 on: September 03, 2010, 11:26:22 AM »
Hey Oogie,

I think you'll planning to synthetize this molecule :




I already tried the salicylic form with very good results  ;D

==>



I doubt the acetoxy form will do anything.


edited.
« Last Edit: September 03, 2010, 02:37:50 PM by NaBH4 »
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jon

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Re: kitchen-tek cocaine analog? 3-psuedotropyl-ortho-hydrox/acetoxy-tropane
« Reply #2 on: September 03, 2010, 02:29:06 PM »
you drew that wrong but are you talking about saliciloyl cocaine?

i've always wondered how that stuff was?
how is the high?
i mean something that tickles the yay g-spot 10 times more effective than coke has to be fun.
« Last Edit: September 03, 2010, 02:31:24 PM by jon »

NaBH4

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Re: kitchen-tek cocaine analog? 3-psuedotropyl-ortho-hydrox/acetoxy-tropane
« Reply #3 on: September 03, 2010, 02:41:43 PM »
I edited my pics. Is it better now ?  ;D

So, i synthetized Saliciloyl Tropacocaine from (pseudo)tropine reacted with Salicylic Chloride.

Naphyrone and me arn't talking about cocaine analogue dude but simply Tropacocaine substituted analogues.


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Naphyrone

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Re: kitchen-tek cocaine analog? 3-psuedotropyl-ortho-hydrox/acetoxy-tropane
« Reply #4 on: September 03, 2010, 02:50:41 PM »
NaBH4, why did you bother with salicylic chloride when you could have just done a Fischer-Speier esterification?
Have you tried the esterification of tropine/3-tropanol with salicylic acid?
Also what is the best way to re-crystallize the Saliciloyl Tropacocaine and how would you rate potency compared to cocaine?
Doing the esterification what is the ratio you would use and what acid for catalyst?

NaBH4

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Re: kitchen-tek cocaine analog? 3-psuedotropyl-ortho-hydrox/acetoxy-tropane
« Reply #5 on: September 03, 2010, 02:58:26 PM »
I did the esterification with salicylic chloride because it has better yield than simply salicylic acid.
Recrystalisation in sulfate are the best for me (i tried hydrochloride and citrate form). I can assume it's the same potency as cocaine but ...that's deafinitaly not coke (can't explain why  ???)

Same stimulation / self-confidence as cocaine.
Weak euphoria.

For the Fisher Speier esterification i'd use conc. sulfuric acid. I guess it'll work well.
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Naphyrone

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Re: kitchen-tek cocaine analog? 3-psuedotropyl-ortho-hydrox/acetoxy-tropane
« Reply #6 on: September 03, 2010, 03:18:25 PM »
Interesting, coke never gave me much euphoria to begin with, just an obnoxious frat boy type ego. Could you do a quick write up for the fischer-speier esterification, I know i will need more weight in tropine than salicylic acid but im just not worth shit when it comes to accurate math.

Naphyrone

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Re: kitchen-tek cocaine analog? 3-psuedotropyl-ortho-hydrox/acetoxy-tropane
« Reply #7 on: September 03, 2010, 03:50:58 PM »
Also on the topic of euphoria, I bet it is from reduced SERT inhibition.
Try the nortropine variety yet? I vaguely recall someone on BL saying something about tropane analogs getting more 5HT activity with the N-methyl removed.
« Last Edit: September 03, 2010, 03:57:59 PM by Naphyrone »

NaBH4

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Re: kitchen-tek cocaine analog? 3-psuedotropyl-ortho-hydrox/acetoxy-tropane
« Reply #8 on: September 03, 2010, 03:57:50 PM »
Nor-saliciloyltropacocaine ?
Yeap, that's a good idea  :P

I'm actually trying to put that goddamn propanoyl group but i'll try to N-demethylate my Saliciloyl tropacocaine next week  ;D
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Naphyrone

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Re: kitchen-tek cocaine analog? 3-psuedotropyl-ortho-hydrox/acetoxy-tropane
« Reply #9 on: September 03, 2010, 04:07:17 PM »

jon

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Re: kitchen-tek cocaine analog? 3-psuedotropyl-ortho-hydrox/acetoxy-tropane
« Reply #10 on: September 03, 2010, 04:08:04 PM »
i don't know about doing a fisher esterification on that because you want to pervent the beta hydroxy group from epimierizing correct?

Naphyrone

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Re: kitchen-tek cocaine analog? 3-psuedotropyl-ortho-hydrox/acetoxy-tropane
« Reply #11 on: September 03, 2010, 04:29:12 PM »
Vesp, you finally have a use for your datura and something you can use aspirin as a starting material for. :P

jon

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Re: kitchen-tek cocaine analog? 3-psuedotropyl-ortho-hydrox/acetoxy-tropane
« Reply #12 on: September 03, 2010, 04:34:31 PM »
it is'nt as "fun" as cocaine???

Naphyrone

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Re: kitchen-tek cocaine analog? 3-psuedotropyl-ortho-hydrox/acetoxy-tropane
« Reply #13 on: September 03, 2010, 04:42:05 PM »
NaBH4 what do you think salicyl-3-scopine would do?
Just curious because if one were to mess up the extraction and purification of atropine from datura then i woulf fully expect scopine variant to be an impurity.
That said, I wonder what in the hell the effects of the compound would be.

NaBH4

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Re: kitchen-tek cocaine analog? 3-psuedotropyl-ortho-hydrox/acetoxy-tropane
« Reply #14 on: September 03, 2010, 05:36:03 PM »
Naphyrone, I want to put a propanoyl group and not a carbomethoxy group on that goddamn tropinone ^__^
I think propionic chloride will do that if the 3rd position (3=O) is protected.

Jon, Salicyl-tropacocaine is fun but that's definitaly not cocaine. It certainly better than street cocaine but not as good as good grade cocaine :)


@Naphyrone :
For the salicylic analogue of tropacocaine, I started with pure Tropinone (bought in china uh uh) because I didn't manage to get my hand on a selective extraction protocol of datura or nightshade.

But you're right : What the well could do the Scopolamine version of this compound ? oO
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Vesp

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Re: kitchen-tek cocaine analog? 3-psuedotropyl-ortho-hydrox/acetoxy-tropane
« Reply #15 on: September 03, 2010, 10:38:26 PM »
Wow, your right this looks like an easy synthesis, even including getting it from datura.
Very interesting, great thread!
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Naphyrone

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Re: kitchen-tek cocaine analog? 3-psuedotropyl-ortho-hydrox/acetoxy-tropane
« Reply #16 on: September 04, 2010, 01:35:58 AM »
How much does succindialdehyde run for and is it watched? Because tropine that iv'e sourced is expensive and i'm not sure if I want to work with large quantities of anticholinergics. I mean the thought of having to move around 500+ml of datura/brugmansia alkaloid extract kinda scares me :'(.

Vesp

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Re: kitchen-tek cocaine analog? 3-psuedotropyl-ortho-hydrox/acetoxy-tropane
« Reply #17 on: September 04, 2010, 01:43:04 AM »
There wouldn't be any chances of improving the yield by ways of transesterification of say atropine with the salicylic acid, or methyl salicylicate?
or even a tranesterification of methyl salicylicate with tropine?
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Naphyrone

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Re: kitchen-tek cocaine analog? 3-psuedotropyl-ortho-hydrox/acetoxy-tropane
« Reply #18 on: September 04, 2010, 03:34:35 AM »
Thank you wolfram alpha for telling me about the properties of atropine and scopolamine...

Scopolamine:
molecular weight | 303.353 g/mol
phase | solid  (at STP)
melting point | 59 °C

experimental LogP hydrophobicity | 0.8
predicted LogP hydrophobicity | 1.4
predicted LogS | -1.66
experimental Caco2 permeability | -4.93

Atropine:
molecular weight | 289.369 g/mol
phase | solid  (at STP)
melting point | 115 °C
boiling point | 393 °C

experimental LogP hydrophobicity | 1.8
predicted LogP hydrophobicity | 2.19
experimental LogS | -2.12
predicted LogS | -2.06

This should help with separation after extraction  ;D (i love the internet)

Would one be able to use a long chain alcohol say, cetyl alcohol to separate the atropine from scopolamine effectively?
My idea is take the alkaloid salts, put them in cetyl alcohol thats been heated to 51*C, the scopolamine is heavier than the alcohol thus should sink to the bottom in theory.
Scoop out the atropine salt then with a clean batch of the cetyl alcohol heat it to 62*C to melt any scopolamine that is hanging onto the atropine salts, stir, let sit at this temp.
Scoop out the atropine salts once again, let them cool off, dissolve in seperatory funnel with water. Shake, then let any cetyl alcohol separate from the water. (Recrystalize atropine???) Move to hydrolysis process.
« Last Edit: September 04, 2010, 04:19:37 AM by Naphyrone »

Naphyrone

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Re: kitchen-tek cocaine analog? 3-psuedotropyl-ortho-hydrox/acetoxy-tropane
« Reply #19 on: September 04, 2010, 11:02:57 AM »
 http://books.google.com/books?id=CT63dsYHtG4C&pg=PA652&lpg=PA652&dq=scopoline+benzoic+acid&source=bl&ots=I6gokdgzb_&sig=4FVhDoIQLLuhgQ5qAlqQG_4Nw00&hl=en&ei=WyGCTICgO8WBlAecjbmkDg&sa=X&oi=book_result&ct=result&resnum=1&ved=0CBIQ6AEwAA#v=onepage&q=scopoline%20benzoic%20acid&f=false

salicyl scopine/scopoline according to that book produces needles insoluble in water, this is good because im pretty sure the salicyl tropane dissolves in water (it does right NaBH4?).
By the way Vesp, datura stramonium has a higher ratio of atropine to scopolamine than datura innoxia. hyoscyamus muticus (egyptian henbane) contains an average of 1.5% alkaloids by weight most of it being atropine and hyoscamine(isomer) with very little scopolamine.
« Last Edit: September 04, 2010, 11:15:59 AM by Naphyrone »