Eters of Ethanol

[c0rt3x]

EDIT: Sorry the title contains a typo: I meant "Esters of Ethanol" of course.

I've synthesised some ethers of ethanol in order to research them. First I made Ethyl acetate wich isn't enjoyable at all in my opinion. The second one was Ethyl chloride also known as Chloroethane. This compound seems to be far more interresting since wikipedia says:

Ethyl chloride is a recreational inhalant drug, sometimes referred to as "Duster". Similar to poppers, ethyl chloride is used as an inhalant (huffed) during sexual activity for an intense several-minute-long high that results in a prolonged orgasm. In Brazil, it is a traditional (though illegal) drug taken during Carnaval parades, known as "lança-perfume".

Unfortunately i cant confirm that it leads to a prolonged orgasm ;-). But maybe the dose was to low. Had somebody else had better results with it?


However I will synthesise several other ethanol esters in order to study their effects. I'm interested in: the following esters: The phosphate, citrate, tartrate, glutamate, and of course the ethanol ester of gamma-Aminobutyric acid and (particularly since the last both usually doesn't cross the blood brain barrier) and many more. I think that ofter Ethanol esters of many amino acids could be really be woth a look! I guess the ethanol ester of GHB could be quite interesting as well interesting.

GABA esters and GABA analog esters
United States Patent 5051448

Abstract:
Ester derivatives of gamma-aminobutyric acid (GABA) and GABA analogues which cross the blood-brain barrier are disclosed, as well as methods of synthesizing and using the compounds.

The ester derivatives have the formula: ##STR1## where A is a radical compound having at least one esterifiable OH group; n varies from one to the total number of esterifiable OH group contained in A; and R1, R2, R3 and R4 are hydrogen or a substituent.

Two lipid esters of U-14C-labeled and unlabeled gamma-aminobutyric acid (GABA) were synthesized to test the possibility that natural lipid analogues, which resemble normal components of lipid bilayer membranes, can penetrate the blood-brain barrier and transport exogenous GABA to the brain. The uptake of 1-linolenoyl-2,3-bis(4-aminobutyryl)propane-1,2,3-triol and 1,2-dilinolenoyl-3-(4-aminobutyryl)propane-1,2,3-triol into mouse brain relative to liver was found to be, respectively, 75- and 127-fold greater than that of free GABA. The results indicate that there is little or no blood-brain barrier for the GABA ester molecules at doses up to 0.36 mmol/kg. Both ester compounds, but neither free GABA nor the lipid components delivered systemically, demonstrated central nervous system depressant properties by inhibiting the general motor activity of mice. Brain tissue has esterase activity which can release GABA from these compounds. This suggests that these compounds function as "prodrugs" to release GABA in the CNS.

Has anyone some more suggestions?

 

[Kanga]

EDIT: I got confused.

 

[chloral hydrate]

The only thing I can think of is diethyl ether, sorry. That would be quite easy to make and it's a decent anesthetic, only thing is you get really unpleasant nausea-like from it after the buzz goes away

Kanga: now I feel bad for telling you it's not ethyl chloride there in those cans 8)

 

[Quanta]

whoa, c0rt3x slow down there buddy Suggestion, don't go inhaling alkylating agents. Make the ethyl ester of glycine and your one step from nordiazepam which is pratically indistinguishable from valium.

 

[chloral hydrate]

I was thinking that too, how come methyl chloride is so fucking corrosive and poisonous but ethyl chloride is ok?

Really, nordiazepam? source?

 

[Quanta]

Common reaction in benzo preparation (simple condensation with a substituted aminobenzophenone) - all throughout the literature. If it is a patent you like....WO/1996/005178

 

[chloral hydrate]

diethyl ether is ok. If you have nothing else lying around, pour or spray some on a piece of paper towel until it's kinda wet and keep inhaling deeply... it will kind of tickle your throat and towel will quickly become totally dry. What sucks is how you feel afterwards- nauseous. The only thing to make it go away is to huff some more ether, and I usually keep doing this until I'm almost out.

 

[Swerlz]

There is nothing in the world more helpless and irresponsible and depraved than a man in the depths of an ether binge.

 

[chloral hydrate]

Oh I completely missed the original post. That GABA ethyl ester BBB crossing does seem extremely interesting. I wonder what else you can ethylate- he's already tried phenylalanine don't know how that worked out. Where are you cortex?

 

[onmyway]

guys, don't huff shit. Unless I'm mistaken this is a harm reduction forum. Organic solvents are bad for you.

 

[Jamshyd]

^ Exactly.