Author Topic: 4-ace-det solubility?  (Read 5596 times)

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madprosr

  • Guest
4-ace-det solubility?
« on: January 28, 2002, 10:42:00 PM »
swim dreams of encasing ace-det in hard gelatin cubes for ease of storage and division.
ace is freebase, so it should bee insolube in water until acidified to slightly below neutral.
is a strong acid more effective than a weak one for this?
furthermore however, swim has heard some acids (citric, etc) interfere with the hardening of gelatin...

so swim asks if anyone knows what organic co-solvents are good for the ace?
(chemfinder lacks ace and a merck is *not* handy)
how about 50-75% EtOH/water such as vodka or 151 rum?
EtOH is non-toxic and miscable with gelatin

so, swim hopes .1g / 10mL will dissolve (on hot water bath) to which .2-.3g of pure gelatin would be added slowly, with gentle stirring to prevent clumping / introducing bubbles, stopping before mixture becomes too viscous to pour easily onto an engraved tray to dry.

swim just isn't satisfied with liquid measure as a dosing strategy, longtime lurker, would appreciate any comments...
sorry for double-posting, this needs a new thread.

Lem2

  • Guest
Re: 4-ace-det solubility?
« Reply #1 on: January 29, 2002, 05:09:00 AM »
careful with the 4-HO/4-AcO cmpds. they tend to decompose in rection to light and heat.

He who makes a beast of himself gets rid of the pain of being a man.

dely72

  • Guest
Re: 4-ace-det solubility?
« Reply #2 on: January 29, 2002, 10:36:00 AM »
Well, actually the freebase should still be soluble in water. While DET is very non-polar, it's 4acetoxy counterpart is, thus it is very possible that it is soluble in water. The same holds true for psilocybin as well, which is why it harder to extract than DMT.

Lilienthal

  • Guest
Re: 4-ace-det solubility?
« Reply #3 on: January 29, 2002, 05:49:00 PM »
No, no, no. Psilocin and O-acetyl-psilocin are not watersoluble (in their base form)!  In contrast to psilocybin with it's zwitterionic structure.

Psilocin is not thaaat unstable (as long as you don't treat it with base). O-acetyl-psilocin is pretty stable, I wouldn't worry about it's stability.

The same should be true for the ethyl analogs.

madprosr

  • Guest
Re: 4-ace-det solubility?
« Reply #4 on: January 30, 2002, 06:54:00 AM »
ok, swim dreamed the ace dissolved easily in 151 rum.
.1g in 1-2mL or so without heat. some of it turned from offwhite/gray to orange before dissolving though...?

so it was placed on a hot water bath and 30mL tap water was added. soln was completely clear.
1.5g pure gelatin was stirred in cautiously.
it was then poured into a small metal tray. additional hot water dissolved the residue and was added to the tray.

after 12 hours drying, gel was clear and still too rubbery to cut without tearing.
after 24 hours, gel turned quite thoroughly orange  :o , is firm enough to slice, and no longer smells of alcohol.

hopefully swim will dream about it again tonight and see if the potency is affected.

madprosr

  • Guest
Re: 4-ace-det solubility?
« Reply #5 on: February 04, 2002, 10:39:00 AM »
swim dreamed faint waves of blackness spread through the gelatin as it finally hardened.
similar color to the ace-det decomposition pics on erowid.

ahh well, swim dreams of gelcaps now...

foxy2

  • Guest
Re: 4-ace-det solubility?
« Reply #6 on: February 04, 2002, 02:04:00 PM »
so did you eat the jello?
How was it?

Fully Informed Jury!

(http://www.fija.org/)

sunlight

  • Guest
Re: 4-ace-det solubility?
« Reply #7 on: February 04, 2002, 06:13:00 PM »
My question is how have you made 4 acetoxy DET...

madprosr

  • Guest
Re: 4-ace-det solubility?
« Reply #8 on: February 05, 2002, 09:24:00 AM »
swim dreamed the sheet of orange gelatin was indeed active.
but he has not yet dreamed of dissolving a similar dose in liquid for comparison...

it was just such a shame to see it decomposing. maybe using tap water or exposing it to light was responsible (and avoidable in the future), but oxidation on the surface is most likely.

as for how swim 'made' it...
swim has never dreamed a more complicated synth than ghb (or asprin, heh).
though he dreamed about a f*cked up and fruitless dcm a/b extraction from mimosa hostilis complete with evil emulsions, MgSO4, and homemade hcl gas for 3 consecutive nights once.

actually,
swim dreamed his source just told him it is ace-det hcl salt, not freebase.
which should bee the more stable of the 2 anyway..!

sunlight

  • Guest
Re: 4-ace-det solubility?
« Reply #9 on: February 05, 2002, 05:22:00 PM »
Well, then my question for the good chemists is how to convert 4-OH dialkyl triptamine to the acetoxy derivative.

Rhodium

  • Guest
Re: 4-ace-det solubility?
« Reply #10 on: February 05, 2002, 05:54:00 PM »
I believe that transformation is already made as the first step on the indole, I can't think of any way to make 4-OH-DET without a protected phenol.

4-Acetoxyindole from 4-Hydroxyindole

4-Hydroxyindole (7.6g, 57 mmol) was dissolved in 200ml of pyridine and 150 ml of acetic anhydride was added. The reaction mixture was stored at room temperature for 18 hours. The solvent was removed under vacuum, and the residue co-distilled with 2x100ml toluene. The solid residue was recrystallized from cyclohexane to give 8.07g (81%), mp 98-100°C.

Reference: J. Heterocyclic Chem. 14, 71-74 (1977)

madprosr

  • Guest
Re: 4-ace-det solubility?
« Reply #11 on: February 05, 2002, 06:36:00 PM »
now swim already dreams of a nice happy fungus colony under his bed...

but out of curiosity,
1) are pyridine fumes dangerous?
2) to co-distill one would dissolve the 4-acetoxy-indole residue in tolulene then strip all the tolulene off? or does the 4-acetoxy-indole boil first leaving heavier impurities in the tolulene?
3) in the ace-dmt ref on rhodium's page 4-benzyloxy-indole is plugged into shulgin's dmt synth via oxalyl chloride in Et2O, then dimethylamine in Et2O to indol-3-yl-N,N-dimethylglyoxylamide, then after reduction with LAH in THF to 4-benzyloxy-dmt converted to 4-acetoxy-dmt.
can 4-acetoxy-indole be substituted initially?
equally true for dimethylamine, diethylamine, and diisopropylamine?

oh, and something unrelated,
anyone know Gartz' or another method to add tryptamines to cubensis fruiting bodies for 4-hydroxylation? could a small quantity be injected with a blunt-tipped syringe?
swim dreams he has some dpt freebase  ;)  and an urge to chart a new frontier or 2.

Lilienthal

  • Guest
Re: 4-ace-det solubility?
« Reply #12 on: February 05, 2002, 06:38:00 PM »
The acetoxy group will be split off during alanate reduction and has to be introduced again later.

Lilienthal

  • Guest
Re: 4-ace-det solubility?
« Reply #13 on: February 05, 2002, 07:08:00 PM »
> 1) are pyridine fumes dangerous?

Before you reach toxic doses you have already left the house... pyridine has a HIGHLY unpleasant odor... Triethylamine is a good substitute.

> 2) to co-distill one would dissolve the 4-acetoxy-indole residue in tolulene then strip all the tolulene off? or does the 4-acetoxy-indole boil first leaving heavier impurities in the tolulene?

I think it means to add fresh toluene to remove traces of pyridine.

I would suggest the following: acetanhydrid, triethylamine (maybe org. solvent), let react, add water to destroy excess acetanhydride (or distill most of it off), basify, partition between water and organic solvent (to remove the acetic acid), wash again with acidic water (to remove the organic base), wash to neutrality with water, dry (MgSO4), and evaporate. Then vacuum-distill the acetoxy-indole.

> 3) in the ace-dmt ref on rhodium's page 4-benzyloxy-indole is plugged into shulgin's dmt synth via oxalyl chloride in Et2O, then dimethylamine in Et2O to indol-3-yl-N,N-dimethylglyoxylamide, then after reduction with LAH in THF to 4-benzyloxy-dmt converted to 4-acetoxy-dmt. can 4-acetoxy-indole be substituted initially?

Yes.

> equally true for dimethylamine, diethylamine, and diisopropylamine?

Yes. Yes. Possibly (diisopropylamine is sterically hindered, the reaction conditions are probably much, much harsher.)

I would suggest a view into the original literature (which can be found under

http://www.fortunecity.com/westwood/storey/116

)