# Least Toxic, Most Effective, Most Concealable Alcohol?



## seep

DISCLAIMER: I'm drunk.

I've come to the conclusion that I'm powerless over my inhibitions and that a higher power exists that can restore me to sanity. That higher power is booze. But I can't drink at work, and drinking at school got me sent home from lab last week (and my idiot lab partner screwed up the recrystallization and we got a meager 18% yield, but that's OT).

And then so then but then there's scattered all over ADD proposals and testimonials concerning *Alcohols that are less toxic, more efficacious and less smellable-on-the-breath than ethanol*. These are scattered pell-mell on this blog and as far as I know they've not formally been gathered into one thread. I know that Hammilton, F&B and Negrogesic have written about substances such as chlorbutanol, 2-methylbut-3-yn-2-ol and some lavishly-praised cyclic alcohol. These are examples.

And then so then but then I was wondering if we can't settle on an alcohol which can be consumed as chronically as ethanol is consumed but that is easier on the liver and lighter on the olfactorium. A room-temperature solid would be especially fantastic, as one could just stir it into his or her or my beverage of choice.

Thanks.


----------



## xxl

I don't think any other alcohol than ethanol is drinkable. And many are highly toxic. 

The word "alcohol" only designates a function in organic chemistry (the -OH function), ie the family of compounds to which ethanol belongs. Families of organic compounds will contain few members which are drinkable/eatable, and a majority of members which cannot be swallowed or even inhaled without causing harm.


----------



## /navarone/

I know that GBL and GHB feel a lot like alcohol for some people.

Gabapentin and Pregabalin are also similar...but a substance that feelx exactly like alcohol..hmm dunno.

I know of a new research benzodiazepine that supposively mimics the effects of alcohol.


----------



## /navarone/

The problem with alcohol toxicity isnt majorly the damage dome during intoxication but the damage made by their metabolites.
ethanol is metabolized into acetaldehyde which is further on metabolized into acetic acid.

Ethanol and acetic acid aren't really toxic per se but acetaldehyde is.


----------



## daddysgone

xxl said:


> I don't think any other alcohol than ethanol is drinkable. And many are highly toxic.
> 
> The word "alcohol" only designates a function in organic chemistry (the -OH function), ie the family of compounds to which ethanol belongs. Families of organic compounds will contain few members which are drinkable/eatable, and a majority of members which cannot be swallowed or even inhaled without causing harm.



What do you mean that there are no other alcohols besides ethanol that are drinkable?  There are tons.  Some are more toxic then others, but ethanol isn't exactly non-toxic. 

Sorry seep, Im not much of a drinker so I dont know much on this subject.  
GHB/GBL might be a good suggestion since these have a somewhat similar profile to ethanol, and are not terribly toxic.  Unfortunately if you are in the US, these are illegal.

If you want to go the legal route, then phenibut, mixed with a smallish amount of ethanol can produce effects pretty similar to higher dose ethanol intoxication. 

It depends on what you are looking for though really.  If you want to be walking around absolutely smashed, then something like phenibut will not do the trick.  If however you are looking for just a minor head change and something to take the edge off, then phenibut plus a bit of ethanol or another alcohol might be perfect.-DG


----------



## Northside

A few years back someone told me about AWOL which is alcohol with out liquid. It's some kind of device that vaporizes the booze I guess, google it.


----------



## seep

Northside said:


> A few years back someone told me about AWOL which is alcohol with out liquid. It's some kind of device that vaporizes the booze I guess, google it.



The very happy girl with the pigtails and the small dress must be the inventor.

That thing is cool. I'm getting one! I'll tell people it's for asthma. Thanks North.

.......

Guys, a few things: 

I'm restricting my focus to monohydric alcohols without higher-priority functional groups because
AFAIK, none of these are controlled (except ethchlorvynol)
Potable/ingestible alcohols other than ethanol have been discussed here before (I give a few examples in my OP).
As Navarone points out, I'm trying to avoid toxic metabolytes. I'm gonna get drunk repeatedly--the question is with what.

DG, I like the phenibut + low dose ethanol idea.


----------



## indelibleface

I know that someone here on Bluelight ordered some 1-propanol (propyl alcohol) from a vendor and said that it took less for him to get drunk than regular ethanol. I could be mistaken--it might be 2-butanol that he ordered. I can't remember.

Captain Obvious moment: when ingesting any new alcohol, it's important to figure out what metabolites the alcohol is converted into by alcohol dehydrogenase. I believe propanol does not create any especially toxic metabolites. Butanol should convert into butyraldehyde, and then, what, butyric acid? You might just fart rancid butter smell for a few days. Is butyraldehyde toxic? 

Even 2-propanol (isopropyl, or rubbing alcohol) is not especially toxic, and somewhat more potent than ethanol in causing inebriation. The primary metabolite of isopropyl alcohol, acetone, does not have a high toxicity, but probably contributes to the intoxicating properties and thus the CNS-depressive toxicity of the alcohol itself.


----------



## indelibleface

There's also a relatively easy substance to make called chloral (trichloroacetaldehyde) that was famously once used as a common tranquilizer, and probably feels more or less identical to alcohol. From there, it's one step away from chloral hydrate, of course.


----------



## /navarone/

Yeah i would opt for a secndary alcohol with low toxicity. i-propanol (which is converted into acetone seems quite toxic) compared to alcohol.

Have a look at a list of GABAa allosteric modulators and see what you can find.


----------



## seep

Inedible said:


> I know that someone here on Bluelight ordered some 1-propanol (propyl alcohol) from a vendor and said that it took less for him to get drunk than regular ethanol. I could be mistaken--it might be 2-butanol that he ordered. I can't remember.



Thanks. I'll check these out. 



> Captain Obvious moment: when ingesting any new alcohol, it's important to figure out what metabolites the alcohol is converted into by alcohol dehydrogenase. I believe propanol does not create any especially toxic metabolites. Butanol should convert into butyraldehyde, and then, what, butyric acid? You might just fart rancid butter smell for a few days. Is butyraldehyde toxic?



2-butanol's a secondary alcohol, so it'll be oxidized to butanone (assuming it'll undergo oxidation like ethanol). 1-propanol should be just like ethanol: propanal and propionic acid. 



> Even 2-propanol (isopropyl, or rubbing alcohol) is not especially toxic, and somewhat more potent than ethanol in causing inebriation. The primary metabolite of isopropyl alcohol, acetone, does not have a high toxicity, but probably contributes to the intoxicating properties and thus the CNS-depressive toxicity of the alcohol itself.



To be precise, I'm worried about toxification (and of course toxicity (carcinogenicity, neurodegradation, etc). "CNS-depressive toxicity" (read "intoxication") is kinda the goal, no? 

The "tox" morpheme gets tossed around a little loosely. Originally it was a Scythian word for an archer's bow (or the wood it was made from, or the tree (yew) that produced the wood). Hence the greeks would call the poison on their arrows _toxikon_, a substance which was also known by the name _pharmakon_, which is the origin of our word "pharmacology". Drug technology has its roots in hunting.

Jesus I'm stoned.


----------



## seep

/navarone/ said:


> Have a look at a list of GABAa allosteric modulators and see what you can find.



Yeah, are any of these available?

But damnit, you guys keep straying from the monohydric alcohols. Chloral: aldehyde. Chloral hydrate: diol. GABA-A-PAM's: aromatic, polyheterocyclic, etc. 

 Thanks though.


----------



## Psychedelic Jay

Undecanol is around the same in terms of intoxication.
It is insoluble in water.

2-Methyl-2-butanol, is 20 time stonger than alcohol, plus it has the smell of mint.


----------



## seep

Psychedelic Jay said:


> Undecanol is around the same in terms of intoxication.
> It is insoluble in water.



That must smell and taste like slow death.



> 2-Methyl-2-butanol, is 20 time stonger than alcohol, plus it has the smell of mint.



Yes, that's exactly the kind of tree I'm trying to bark up. Let's look into how safe it is. Thanks.

*Edit:* And so but then how is a tertiary alcohol metabolized? They're far less reactive in the lab.


----------



## Psychedelic Jay

Here you are.

http://www.jtbaker.com/msds/englishhtml/a6408.htm

And a trip report.

http://www.bluelight.ru/vb/showthread.php?t=439925

^From this it seems as it is very euphoric.

http://www.bluelight.ru/vb/showthread.php?t=439932&highlight=2-methyl-2-butanol For metabolism.

More on it.
http://www.bluelight.ru/vb/showthread.php?t=435493&highlight=2-methyl-2-butanol


----------



## indelibleface

seep said:
			
		

> 2-butanol's a secondary alcohol, so it'll be oxidized to butanone (assuming it'll undergo oxidation like ethanol). 1-propanol should be just like ethanol: propanal and propionic acid.



Ah, okay, interesting. Not a pharmacologist here; still learning, thanks. 



			
				seep said:
			
		

> To be precise, I'm worried about toxification (and of course toxicity (carcinogenicity, neurodegradation, etc). "CNS-depressive toxicity" (read "intoxication") is kinda the goal, no?



I'm not sure if acetone has been proven to be carcinogenic. I don't know about long term health effects, though. I mean, alcohols have negative effects all over in the long term, anyway. I'm sure acetone is in the same ballpark or slightly worse.

It seems like most simple alcohols have relatively benign metabolites, not counting chronic, long term effects, of which ethanol is no stranger to. Methyl alcohol seems to be an anomaly in that regard. I know that someone here mentioned that butanol might have some relatively more toxic metabolite...someone might want to fill in on that.

EDIT: Ah, butanone is a synonym for methyl ethyl ketone. Wiki claims that toxicity only occurs at very high levels; I wonder if it is really that toxic compared to other alcohol metabolites or acetone.

*fastandbulbous* mentions in another thread 1-ethynylcyclohexanol. Might be worth looking into.


----------



## Psychedelic Jay

Yeah, I am going to get some 2-Methyl-2-butanol, because based on the info, the is no noticeable to note. Plus long duration is a plus for me.


----------



## Serious




----------



## Psychedelic Jay

I know this guy is not looking for hangovers, ethanol will not cut it.


----------



## Serious

Yeah I figured they won't solve everything but at least they are effective and concealable (work, school, etc)


----------



## seep

^Yeah no, by "concealable" I mean I don't want to smell like booze in places where I'm not supposed to smell like booze.

So excluding IPA, sec-butanol and  undecanol (mentioned in this thread but not backed up by assay or anecdote), a pattern emerges among the alcohols that have been certified golden by Bluelighters:






, 
	

	
	
		
		

		
		
	


	




, 
	

	
	
		
		

		
		
	


	




, 
	

	
	
		
		

		
		
	


	




(respectvely, 2-methyl-2-butanol, chlorobutanol, 2-methylbut-3-yn-2-ol and 1-ethynyl-1-cyclohexanol).

See the pattern? *They're all tertiary alcohols.* This is significant because they can't be directly metabolyzed to ketones or aldehydes, so all the ink that has been spilt about the toxicity of aldehyde- or ketone-metabolytes of alcohols does not apply to these.

*So as far as metabolism goes: what happens next? Pharmacokinetic info on these (or the like) please...*

Thanks guys


----------



## seep

seep;8075231[B said:
			
		

> So as far as metabolism goes: what happens next? Pharmacokinetic info on these (or the like) please...[/B]



Answered my own question (I think). They will be primarily converted to a diol by CYP-hydroxylation at the least-hindered carbon adjacent to the original hydroxyl, then they are conjugated and renally-eliminated. (although the alkyne-containing specimens undergo some degree of acetylene oxidation).

Source: Ethchlorvynol's metabolism as detailed on page 9 here.

If someone with insight on this can comment if this is correct, please do.


----------



## vecktor

several of the above alcohols are controlled drugs so not viable as substitutes for etoh

anything that metabolizes to butyric acid should be avoided the stuff does not just smell rancid, in low concentrations the stench of vomit is very powerful and is intensely unpleasant. the smell incidentally is worse the more the stuff is diluted.


----------



## Holy_cow

3-Methyl-3-pentanol might be a good idea, it's the active metabolite of Emylcamate and thus should have a similar dose as Emylcamate (200-400mg). It's commercially available from China (1kg @ US$250 including shipping) and elsewhere. Considering that you get some 2000 drinks from a kg, it's not all that expensive. Aldrich offers it, too, for a similar price: 3-Methyl-3-pentanol
≥99%, Kosher, 1kg @ 260.00€. I haven't tried it, though.

I hope this is not considered sourcing. Else please edit accordingly, Mods.


----------



## /navarone/

I guess tertiary alcohols won't be metabolized, they'll prob get out as they came in, i don't se how they could be broken down or bond to someting else.

I'm a booze lover too, however seep, I sincerely think you should deal with your psychological fondness of alcohol.
From the thread it seems that you are seeking a chemical that will make you feel drunk but without the risk of other noticing it while in a professional situation.
From my point of view ordering gallons or strange alcohol from a chemical supplier is really exagerated.

Then if your post is mostly aiming at finding healthier alcohols....well, I'm with you bro!!


----------



## Psychedelic Jay

It is not even near gallons. That would be too much. especially to just have at hand like that.

I hope that we can all ban together and get rid of ethanol as a beverage, and concentrate it for fuel.


----------



## pofacedhoe

seep said:


> Thanks. I'll check these out.
> 
> 
> 
> 2-butanol's a secondary alcohol, so it'll be oxidized to butanone (assuming it'll undergo oxidation like ethanol). 1-propanol should be just like ethanol: propanal and propionic acid.
> 
> 
> 
> To be precise, I'm worried about toxification (and of course toxicity (carcinogenicity, neurodegradation, etc). "CNS-depressive toxicity" (read "intoxication") is kinda the goal, no?
> 
> The "tox" morpheme gets tossed around a little loosely. Originally it was a Scythian word for an archer's bow (or the wood it was made from, or the tree (yew) that produced the wood). Hence the greeks would call the poison on their arrows _toxikon_, a substance which was also known by the name _pharmakon_, which is the origin of our word "pharmacology". Drug technology has its roots in hunting.
> 
> Jesus I'm stoned.



you always have interesting things!


----------



## agram

I can't say that I have anything valuable to add to this, but I really hope this topic blooms. I think a good alternative has been a long time coming, and would be great for many, not just the OP. 

Now, where's my whisky and pipe... 

And damnit, the woman didn't bring me my slippers. Or stoke the fireplace. It's going to be a hard night, I think.


----------



## Hammilton

Here's a simple suggestion:  Look at the scheduled carbamates, and imagine them as alcohols.  AFAIK, all of the alcohol derivatives of carbamates are active.  the ones I'm unsure about are meprobamate and carisoprodol, but I'd be surprised if they were inactive.

Still, go the cheaper to produce drugs.  1-ethynyl and 1-propynyl 1-cyclohexanol are both active, fairly potent, and enjoyable by all accounts.   I recently tried 1-propynyl and found it quite pleasant, but it strongly potentiated my suboxone, similar to low doses of phenobarbital, at even a low dose and I was hesitant to try a higher dose as long as I'm on the suboxone.


----------



## Psychedelic Jay

In my opinion, those are to potent for the everyday user.
If you plan on doing large quantities then these can be quite a lot more dangerous for undiluted solutions.


----------



## seep

Hammilton said:


> 1-propynyl 1-cyclohexanol



I assume you tried the propargyl, but I have to ask:






 or 
	

	
	
		
		

		
		
	


	




?

Holy Cow, good point about 3-methyl-3-pentanol. Both of you are thinking along the same lines.

Navarone, 



> I guess tertiary alcohols won't be metabolized, they'll prob get out as they came in, i don't se how they could be broken down or bond to someting else.



I think they're mostly glucuronidated, but some CYP450 oxidation takes place, especially if the structure has allylic carbons. Like, see here:

ALIPHATIC ACYCLIC AND ALICYCLIC TERPENOID TERTIARY ALCOHOLS AND STRUCTURALLY RELATED SUBSTANCES


----------



## Psychedelic Jay

Potency is still an issue here people.


----------



## seep

Psychedelic Jay said:


> Potency is still an issue here people.



This is also complicated when everything is being compared to ethanol, because acetaldehyde has such a profound effect on the body at high doses. There's a post from phasedancer that points out one aspect of the magnitude of this. Consider that to metabolize a mole of ethanol (which is 6-8 drinks, depending on who's tending bar), the body needs to reduce 2 moles of NAD+. That's 1.3 kg of NAD+!

So then any published report that states that something is n times as potent as ethanol needs to have taken this systemic effect into account.


----------



## Psychedelic Jay

So, not to be off topic, but based on what you said, nicotinic acid amide can be used for hangovers?


----------



## Hammilton

seep said:


> I assume you tried the propargyl, but I have to ask:
> 
> 
> 
> 
> 
> 
> or
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> 
> ?




Propynyl, the latter of the images.  Ethnyl was similarly good, but IIRC, somewhat less potent.


----------



## Psychedelic Jay

Psychedelic Jay said:


> So, not to be off topic, but based on what you said, nicotinic acid amide can be used for hangovers?



Wow, slipping away unnoticed.


It does make sense that potency is really shallow with Ethnyl.


----------



## Hammilton

It does?  I don't see any sense in it.  At that point there's no simple increase with weight.


----------



## Psychedelic Jay

Look at the molar differences, just like seep said, it will clearly come to you.


----------



## >Marquis<

I know this is a little OT, but is the OP totally unconcerned with neurodegeneration?


----------



## DexterMeth

Hammilton said:


> Here's a simple suggestion:  Look at the scheduled carbamates, and imagine them as alcohols.  AFAIK, all of the alcohol derivatives of carbamates are active.  the ones I'm unsure about are meprobamate and carisoprodol, but I'd be surprised if they were inactive.
> 
> Still, go the cheaper to produce drugs.  1-ethynyl and 1-propynyl 1-cyclohexanol are both active, fairly potent, and enjoyable by all accounts.   I recently tried 1-propynyl and found it quite pleasant, but it strongly potentiated my suboxone, similar to low doses of phenobarbital, at even a low dose and I was hesitant to try a higher dose as long as I'm on the suboxone.



Did the 1-proprynyl literally potentiate the effects of the buprenorphine or add all-around qualitative effects?


----------



## Psychedelic Jay

I am gonna say it added to the effects.
I'm gonna say it acted to opiates just like ethanol.


----------



## Psychedelic Jay

>Marquis< said:


> I know this is a little OT, but is the OP totally unconcerned with neurodegeneration?



What made you say this?


----------



## DexterMeth

^ya, I don't understand how it could of literally potentiated the bupe.


----------



## seep

Psychedelic Jay said:


> So, not to be off topic, but based on what you said, nicotinic acid amide can be used for hangovers?



I don't know that anything is more than marginally effective for hangover. Even if there were such an antidote, and you wouldn't have to ration cellular respiration, clearance of the aldehyde is still going to be sluggish. So then the carbonyl lingers in large quantities and is prone to nucleophilic attack and can become covalently bonded to tissue. Also, it induces enzymes that generate reactive oxidative species as byproducts.

Not to mention the fact that CYP2E1 oxidizes ethanol in the brain. This is bad because the byproduct of this conversion is peroxide. Look at the figures at the end of this paper:

Mechanism of alcohol-induced oxidative stress and neuronal
injury


----------



## DexterMeth

Jesus I can't believe how resourceful the human body is at staying alive from all these insaine polutants we use.


----------



## Psychedelic Jay

It's all homeostasis man.
Like my science teacher used to say when he got sick.


----------



## negrogesic

Perhaps a carbinol, like methylparafynol


----------



## >Marquis<

Psychedelic Jay said:


> What made you say this?



Sorry, is that sarcasm because I made a speculation that had been automatically deemed redundant by all the other posters due to its obviousness, or is that genuine curiousity? I'm not trying to be an asshole I just can't discern the intent of your question...


----------



## Hammilton

negrogesic said:


> Perhaps a carbinol, like methylparafynol



a carbinol?  that's just methylpentynol, a ring opened analogue of 1-ethynyl-1-cyclohexanol.


----------



## negrogesic

Right, but it still appears to be a tertiary carbinol....


----------



## bighooter

If you get a hangover from alcohol then its obviously pretty damn toxic to you.
However if you dont get a hangover then its not too bad.


----------



## Psychedelic Jay

Yeah, it's only more toxic in terms of CNS depression.
I'm guessing since it is easier to O.D. on.


----------



## Hammilton

Emylcamate is still my pick to be one of the big new RC drugs.  I'll be surprised if it doesn't end up as big as mephedrone.  certainly safer.


----------



## ziddy

Hammilton said:


> Emylcamate is still my pick to be one of the big new RC drugs.  I'll be surprised if it doesn't end up as big as mephedrone.  certainly safer.



http://en.wikipedia.org/wiki/Emylcamate

Patented in 1961...not exactly "new" now is it?


----------



## seep

>Marquis< said:


> I know this is a little OT, but is the OP totally unconcerned with neurodegeneration?



Actually my primary concern has shifted to my gut (ouch!)


----------



## daddysgone

ziddy said:


> http://en.wikipedia.org/wiki/Emylcamate
> 
> Patented in 1961...not exactly "new" now is it?



He obviously meant "new on the research chem. scene" and not that its a new drug.-DG


----------



## gladiolus

Hi All,
Very interesting discussion! It’s motivated me to have a comparative look. Below is a list of 17 alcohols with an indicator of their toxicities, their LD50 oral, rat. 1 of these alcohols was taken from www.jpet.aspetjournals.org/content/115/2/230.abstract, some others from www.toxsci.oxfordjournals.org/cgi/reprint/49/1/133.pdf and the remainder, ones already in suggested in this thread and other similar alcohols on this board. Better of all would be some sort of index of intoxication, which is not only hard information to come by, but also a bit of a vague parameter. I’ll talk about this at the end. As a comparator, ethanol is around 7g/kg but some studies indicate around 10g/kg, methanol is listed as 5.6g/kg (I always thought methanol was 5 times as toxic as ethanol, go figure!)

1)  1-propanol			8g/kg
2)  isopropanol		                4.4g/kg
3)  1-butanol			4.3g/kg
4)  1-pentanol			2.2g/kg
5)  1-hexanol			0.72g/kg [another study says 3.1-4.9g/kg]
6)  1-heptanol			3.25g/kg
7)  1-octanol			3.2g/kg

8)  2-methyl 2-butanol	                1g/kg
9)  3-methyl 3-pentanol	                0.71g/kg
10)2-methyl 2-propanol	                3.5g/kg   	(tert-butanol)

11)2-methyl 2-propen-1-ol	                no oral data
12)2-methyl 3-buten-2-ol	                1.8g/kg
13)3-methyl 2-buten-1-ol	                0.81g/kg
14)2-methylbut-3-yn-2-ol	                1.95g/kg	(3-methyl butynol)
15)3-methyl 1-pentyn-3-ol	                0.3g/kg

16)1-ethynyl cyclohexanol	                0.585g/kg
17)2-phenyl 2-butanol		1.4g/kg	


Now the only data I can find regarding intoxication volume-for-volume parameters is roughly this:

1-propanol ~2-4 times 
isopropanol ~2.5 times
1-butanol ~9 times
2-methyl 2-butanol ~17 times
1-ethynyl cyclohexanol ~50 times (based on bluelight reports)

which results in an intoxication-toxic (compared to ethanol 10g/kg) index of

2.4 for 1-propanol
1.1 for isopropanol
3.8 for 1-butanol
1.7 for 2-methyl 2-butanol
2.9 for 1-ethynyl cyclohexanol

making so far, 1-butanol, 1-propanol and 1-ethynyl cyclohexanol clearly more preferable than ethanol to consume. Whether or not the LD50 oral, rat is the best parameter against which to judge toxicity is a major question here. For instance, the ratio indicates that isopropanol is about equal to ethanol. Somehow that’s not convincing enough for me to make a regular switch. There needs to be some sort of consideration of long term non-fatal consumptive effects for this.

Access to intoxicative indicators [or membrane/buffer partition quotients] would be more available had I access to many journal articles. Please contact me with any information you can source and I will update the intoxicative parameters and intoxication-toxic ratios. Can anyone confirm the preferability of 1-propanol? It seems that 1-propanol is metabolized to propaldehyde -> proprionic acid, which looks like pretty nasty stuff to me. If you have a look at the second link I posted above, there’s quite a few measurements of liver activity and so forth linked to a lot of these alcohols that give you more of a picture as to what’s going on. Someone mentioned 1-pentanol as significantly stronger than 1-butanol, for instance, but check out the liver-enzyme stats for pentanol vs. butanol. I know which I'd prefer - pentanol seems to have strange effects on liver O2 consumption, something else quite different is going on here.


----------



## gladiolus

I must also point out that I have discovered 1-ethynylcyclohexanol to be an extremely powerful self-catalyzed "suicide" destructor of cytochrome p450, so you're in the absolute sh*t if you happen to be co-ingesting it with nearly anything else. Looking more and more nasty...so far 2M2B has my bets.

see http://www.pnas.org/content/76/2/746.full.pdf


----------



## ebola?

I know this is obvious, but the OP might have the worst plan for maintenance medication ever conceived. . . 

ebola


----------



## Wizzle

At least it'll _probably_ be better then ethanol.. though I highly doubt it will make a big difference

OT: Too bad I stopped using drugs because this stuff is mighty interesting. keep up the good work guys!..

I have found this great definition in (of course) the _Oxford English Dictionary_ 

2-Methyl-2-Butanonol
2-Me-thyl-2-bu-ta-nol   [too-meh-thil-too-bew-tah-nohl]
–noun
1.
Also called amylene hydrate, 2M2B, Dimethylethylcarbinol, to-mix-to-be-fuckedup, Liquid Panty Remover, supahbeer, secret sambuca. a colorless, limpid, volatile, flammable, water-miscible liquid, C5H12O, having a peppermint like odor and pungent, burning taste, the intoxicating principle of fermented liquors, produced by yeast fermentation of certain carbohydrates, for example grains or obtained synthetically: used chiefly in beverages by adventurous bluelighters, maintenance therapy for helpless drunks, organic synthesis, as an ice queen antifreeze, .Compare ethyl alcohol, methyl alcohol.

_2M2B, the cause of, and solution to all life's problems. _


----------



## gladiolus

How about *2-methyl 2-propyl 1,3 propanediol* [= decarbamated meprobomate]? Do diols count in this discussion? This looks like it would be pretty active, and is about 1.5 times safer than 2m2b and about twice as safe as 3-methyl 3-pentanol.


----------



## Dresden

My vote goes to n-pentanol.


----------



## seep

gladiolus said:


> How about *2-methyl 2-propyl 1,3 propanediol* [= decarbamated meprobomate]? Do diols count in this discussion? This looks like it would be pretty active, and is about 1.5 times safer than 2m2b and about twice as safe as 3-methyl 3-pentanol.



One of the reasons I was interested in excluding diols from consideration (for my purposes) is to avoid any analog-law fuzziness.

Wizzle, funny shit.


----------



## gladiolus

> My vote goes to n-pentanol.



Actually, 1-pentanol is pretty bad if you crunch all the numbers. 1-Butanol comes out much better. See all the links I posted above, and with the glutamate stats from http://www.ncbi.nlm.nih.gov/pubmed/11429388 you'll see that anything above butanol with the primary alcohols is increasingly bad, with respect to molecular weight and LD50 oral, rat; although a case could be made for 1-octanol treatment [which is suprisingly what bigPHARM ARE doing btw]

Another alcohol to consider in the _un_saturated group, is 2-methyl but-3-en 2-ol,[115-18-4] = otherwise the 'n-double carbon bond version' of 2-methyl 2-butanol. There are others, based on the whole methylpentynol/ethchlorvynol thing [i.e 3-methyl pent-1-en 3 ol], but none are as available as this unsaturated version. It also happens to be cheaper than 2-methyl 2 butanol!

Another thing entirely is appropriating the phenyl group. Analogous to phenibut, 2-phenyl butanol might be worth considering.


----------



## its.euphoric

yeah I was gonna say try ghb. it's not bad for you like alcohol.


----------



## dread

its.euphoric said:


> try ghb. it's not bad for you like alcohol.



Stupidest post of the year. Possibly last year too.


----------



## /navarone/

OMG you guys!! this thread has been goin' on for too long.

Just get some good booze and get over it man!!!!


----------



## gladiolus

Secondary researches suggest that the 2m2b molecule is pretty much at the apex of the therapeutic index of alcohols. There seems to be a motif throughout the research, most of it from 70-80 years ago, indicating an increase in therapeutic index with _stressed-carbon bonds _in substitution of the 2-methyl position. One such, mentioned before, as equal to phenobarbitol [in terms of anticonvulsant activity] is the short-lived 2-phenyl 2-butanol. Another study highlights the 2-cyclopropan 2-butanol, and yet another medicine is based on the ethynyl, 2-ethynyl 2-butanol, otherwise 3-methyl pentynol[but see http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2035981/?page=1]

Interestingly, the same report mentions the 2-methyl 3-butyn -2 -ol as being particularly unimpressive. I am given to wonder about the exact properties of the straight 2-ethyl 2-butanol [3-methyl 3-pentanol] - as suggested by another in this thread. My prediction is that 3-methyl 3-pentanol will not have a better therapeutic index than 2m2b - in linear interpolation from the retarded therapeutic index of tri-ethyl carbinol [tert heptanol].


----------



## ZzZzZ

dread said:


> Stupidest post of the year. Possibly last year too.



What's so bad about ghb in reasonable doses?


----------



## Wizzle

Dude is looking for something to basically be drunk all day. Have you ever been high on GHB for a few days straight.. That shit goes bad real quick, and you won't have any regular sleep at all.


----------



## Psychedelic Jay

^^^^^You don't if you are in a real bad hangover either.


----------



## Ne0

Wizzle said:


> Dude is looking for something to basically be drunk all day. Have you ever been high on GHB for a few days straight.. That shit goes bad real quick, and you won't have any regular sleep at all.



That's true about sleeping, Was on GHB 24/7 for few weeks, and in the end I started to get panic attacks and really bad anxiety while sleeping and the dreams were crazy. When stopped couldn't sleep for few days. Tho' still it's better than drinking. Shit is crazy.

Still looking for ACCESIBLE (so no rare chemicals that you can't get) alternative for alcohol/ghb/benzos.


----------



## Psychedelic Jay

You can get all of the thing mentioned here that are not already controlled delivered to your front door, if you really want.

So, there is really no excuse considering a lot of these companies make it on request.
Also, they have no real limit to how much you can buy.
Most of these are used for cleaning.

If you had trouble sleeping anyway, you shouldn't abuse GABA hypnotic drugs. (DUH)


----------



## Ne0

Psychedelic Jay said:


> You can get all of the thing mentioned here that are not already controlled delivered to your front door, if you really want.
> 
> So, there is really no excuse considering a lot of these companies make it on request.
> Also, they have no real limit to how much you can buy.
> Most of these are used for cleaning.
> 
> If you had trouble sleeping anyway, you shouldn't abuse GABA hypnotic drugs. (DUH)



Well its easy to say from USA, since I haven't found any Europan vendors (no that that I am asking them here).

Well the sleep isn't really a problem if you don't go for abusing these drugs, only using alternative for alcohol. The main thing with GHB/GBL is that even if you don't take it for 4h before sleep you still get rebounds and wake up and after that it takes normally 1h to get sleep again if not redosing. At least for me.


----------



## gladiolus

*2 more alcohols to test*

Based on the drug procymate:
1 cyclohexylpropan-1-ol CAS 17264-02-7


Based on the drug phenprobamate
3 phenylpropananol CAS 1335-12-2
OR benzenepropanol CAS 122-97-4
LD50=2300mg/kg (oral, rat)


----------



## bben

least toxic, umm none? Most effective, probably all similar based on proof, and as far as concealable get a flask like everyone else lol.

But seriously, get a different drug, alcohol sucks. There are plenty of easily concealable pills that do what alcohol does much better.


----------



## RobbyG

Ghb and gbl is your solution


----------



## Transform

You need to change your supplier, GBL is solvent only and GHB is solute only. Neither provide the whole solution.

ba-dum tsshh


----------



## atara

seep said:


> And then so then but then there's scattered all over ADD proposals and testimonials concerning *Alcohols that are less toxic, more efficacious and less smellable-on-the-breath than ethanol*. These are scattered pell-mell on this blog and as far as I know they've not formally been gathered into one thread. I know that Hammilton, F&B and Negrogesic have written about substances such as chlorbutanol, 2-methylbut-3-yn-2-ol and some lavishly-praised cyclic alcohol. These are examples.
> 
> And then so then but then I was wondering if we can't settle on an alcohol which can be consumed as chronically as ethanol is consumed but that is easier on the liver and lighter on the olfactorium. A room-temperature solid would be especially fantastic, as one could just stir it into his or her or my beverage of choice.


The chemicals to which you refer are 2-methyl-2-butanol and 1-ethynyl-cyclohexanol. There's also acetophenone and some various carbamate derivatives. Are they safer than alcohol? We don't know. We really don't. They're not-well-studied and their pharmacology is only vaguely understood (we're pretty sure it involves GABA).

GHB gets mentioned a lot too. Is it safer than alcohol? It's somewhat easier on the liver, though neurotoxic and equally addictive. It's more _fun_ than alcohol, and it's also a great hypnotic for occasional use (jet lag, stim comedowns), but it can turn evil fast.

You can't very well go for "safe" when you're talking about taking untested chemicals on a regular basis. You want safe, look at the benzodiazepines, maybe, but be aware that long-term use leads to awful side-effects and benzo dependence can take years to taper off for even the most determined individuals. Also, chronic consumption of large amounts of alcohol ( > 1 g/kg/day) is definitely _not_ safe!

My advice is to look at Jamshyd's ketamine regimen, or to consider aniracetam.


----------



## Hammilton

I wouldn't considered acetophenone to be better than ethanol


----------



## DooMMooD

Everyones bring up how they are potentially "less toxic", but what are we exactly saying?  

Less toxic neurologically?  Less hepatotoxicity?

I will go out on a limb here and say regardless of which alcohol youre ingesting, that *long term* it will still have quite the destructive effect on your liver.  Please guys correct me if i'm wrong on this regarding any of these "different" alcohols.  

What I can say with certainty though:_ liver cancer is no fun_.  In fact, liver damage long term is no fun.  From personal experience with a family member, 9 times out of 10 it will not end well.  Not everyone is lucky enough to get a new liver.

I'm not knowledgeable on any of these, aside from ethanol, so as I stated please feel free to correct my thoughts on the matter.


----------



## 23536

DooMMooD said:


> Less hepatotoxicity?



that was part of the idea.  Ethanol is wickedly toxic to the liver because it's metabolized to acetaldehyde.  Many of the candidates proposed here would not have an oxidative metabolite of similar toxicity.


----------



## delic

I was hoping to see more reports which might narrow down these suggestions. And since the criteria for this thread seems based on biological, toxicological and legal properties, may I suggest not restricting it by chemical functional group? Methaqualone is one of the best alternatives to alcohol I've heard reported. I don't know that it is as toxic - probably not - its main problem is being illegal. But not much effort has been put into solving that problem. And it _does_ stink that one of the world's favorite drugs is so destructive with no good alternative available, and I feel that way despite only drinking moderately a few times a month.

At least I can contribute one report relevant to this thread. I've always wanted to try chloral, but somehow never happening on any, and reading old reports of chlorobutanol being used in a similar capacity, I whipped up a small batch. This is one of the easiest things a person could make, so it seemed very promising. Besides, the product forms large white needles with a strong camphor-like smell, which is rather novel.

The first test of 500 mg dissolved in 10 mL of liquor was mild, pleasant and without any adverse effect.

The second test of 1.5 g in 10 mL of liquor was irritating to the throat for a long time, but came on in just five minutes to my surprise. Very nice and strong, not hard on the body like butanediol (which is worse than GHB for me), but I was surprised when the effects started decreasing as early as 30 minutes and were definitely reduced by one hour. This might have been useful except that by three hours I felt sleepier than I thought I would otherwise, so there seems to be some lingering effect though no toxicity.

Subsequent tests gave less intoxication from this amount and hangover effects of increasing severity which actually lasted longer than they would if caused by alcohol - but without the strong intoxication I might have enjoyed. After a total of six experiments over two months, testing a few dosage formulations, I gave up on this candidate.


----------



## P A

Aside from the varied recommendations of alternative alcohols, I'd strongly suggest that seep eschew unsavory maintenance dosing in favor of cycling daily swigs of ethanol (or a comparable alcohol) and a drug of similar behavioral action to stave off the agony of tolerance-dependence-withdrawal. Hydroxybutyrate, phenibut, high-dose baclofen, or GBL would all be efficient alcoholic counterparts in such a regimen.

Sort of off-topic, yeah, but the notion of consciously committing (resigning?) oneself to alcoholism screams of potential self-harm.


----------



## Transform

I ws looking to update this wiki article but I can't find any good sources which talk about the potential for some alcohols to be safe. That page implies that the alcohol group itself is toxic, but afaik the majority of the toxicity comes from metabolites.


----------



## 23536

Transform said:


> I ws looking to update this wiki article but I can't find any good sources which talk about the potential for some alcohols to be safe. That page implies that the alcohol group itself is toxic, but afaik the majority of the toxicity comes from metabolites.



Ethchlorvynol and one of the alkynes in this thread were used medicinally for decades, so there's that. Chloral hydrate (and therefore chlorbutanol) is still used.  I think it's compelling that many of the toxic metabolites for ethanol & co. are arrived at by oxidation of the -OH group, and that such an oxidation is not possible for tertiary alcohols.

To a certain extent, the word TOXICITY is hopelessly enmeshed with the word INTOXICATION, which is the goal of a recreational alcohol user.  So intoxication without toxicity is a paradox from that point of view.


----------

