1-Ethynylcyclohexanol *LOG*

[interdk]

Hi bluelighters

First of all i would like to tell you guys I LOVE downers (GABA), I have tried different drugs (GABA) such as ethanol, benzoes (no drunkieness), carisoprodol, meprobatmate (no drunkieness), 2-methyl-2-butanol, GHB, methaqualone ("BOSS" from S.A) and so on. But I only do drugs a few times a month.

I have recently acquired 1kg of +99% 1-ethynyl-1-cyclohexanol, and would like to make a log because I don't seem to find MUCH info on here about it.

The drug is solid, but it is not like powder, it looks more like crystals or firbres.
I took 5g of the material and placed it in a glass-cylinder and then put the glass-cyinder in VERY hot water (boiling water) and in seconds it "melted" into liquid (about 5ml).
It does not smell as bad as 2M2B (and the aftertaste is not as bad).

My stats:
M23 l 173cm (5feet'8inch) l 73kg (160 pounds)

LOG (I have been fasting from 18:00):
21:00 l I took 0.1ml to see if any allergic reaction would be present
21:50 l There were no effect, so I took 0.5ml
22:30 l Felt some mild anxiolytic effect therefor I took 0.5ml more
23:45 l No "drunkiness" yet, but only more powerful anxiolytic effect so I took 0.6ml more.
00:50 l Took 0.5ml more
01:45 l Seems a bit intoxicated but not enough, so took 0.5ml more
02:35 l Feels nice, a bit uninhibited and wants to be at a club/bar or something but took 0.5ml more.
03:10 l I feel i little bit drunk but I can still walk "normally" so took 0.5ml more
03:50 l Now i started to feel dizzy and can't think clearly, and I have to close one eye to see whats on the pc-screen and I can't walk properly now, it is about here i like to be.
I feel very tiered and euphoric. I now start to feel the "need" for stimulants (cocaine or speed, as I usually do when doing too high amounts of EtOH or 2M2B)
= TOTAL 3.7ml - BP and HR sayed about the same in all these hours.

i guess 3.2ml would have been enough for me for feeling "good" and social/partymode.
(this MIGHT be a high dose for some, but I have very high tolerance for some drugs, I don't know why, but I only get pissed in the weekends and not even very weekend, it is just my brain chemistry i guess, BTW I cant feel subtle drugs like phenibut and modafinil) I usually do 15-20ml 2M2B so "normal" guys should properly only do half of the dose i did, first time.

I only combined this stuff with Coca-Cola and cigarettes (uses both daily)

This stuff is nice. NO nausea, NO stomach discomfort, and NO bad smell on breath (only a little menthol smell) like 2M2B.

Tomorrow I write here if I get a bad hangover, if NOT this is a great substance.

I have seen some guys on here write about this stuff being bad for the CYP450 enzyme, but I take that with a grain of salt, see all the people who have used this stuff medically (Ethinamate) daily with no bad effect and the people who have used Ethchlorvynol (a triple bound alcohol like this) daily with no ill-effects. So I don't think this stuff is "bad" even though it got ethynyl.

Please come with your inputs.

 

[JacksinPA]

I've gotten interested in this class of GABAergics & have done some research to learn more about which molecules are known to be hypnotics/soporifics & to try to get a handle on the SAR for these compounds. Interestingly, as can be seen in the attached graphics, some of these materials (known as acetylenic carbinols) are also potent stimulants. Unfortunately a major paper where the stimulant compound series is described is a pay site.

I found very little about 1-ethynyl-1-cyclohexanol.

The molecules in red are known & were used in medicine beginning in the 1950s but disappearing with the advent of meprobamate & then the benzos in the 1960s. They range from volataile liquids to solids. The molecules shown came from a cursory literature search of U.S. patents followed by a Google search of their chemical name to identify the ones known to have been used in medicine. The third graphic was playing around with SAR starting with 2M2B.

 

[Scrofula]

Cyclohexanol with an ethynyl:

If you replace the alcohol with a carbamate you get ethinamate, which sounds like a Miltown derivative. And if you sort of double that carbamate into some thing I don't know the name, you get clocental, a sedative from the early days of Bayer.

But OP, who at least survived another fifteen months before going silent, has what is probably the metabolite of that. I don't know how carbamate muscle relaxers interact, but it seems like the crucial moiety, the very essence of their activity, is the carbamate part (and some loose alkyl groups).

Seems like this would be destined for conversion to cyclohexanone in your body (mildly toxic).

I think this chemical was on the market for its potential as a reagent for the arylcyclidine family, not as a chemical for personal oral research.

Unfortunately a major paper where the stimulant compound series is described is a pay site.

The one from 1956 that says "severe" stimulation?

You can see the stimulants are just secondary alcohols destined for ketones, the rest are tertiary, which aren't metabolized.

Really, if you take "Oblivion" and remove the ethyl group next to the alcohol, to make it secondary, you get probable "severe stimulant" 3-butyn-2-ol like the octynol and nonynol.

Which according to the MSDS causes severe, fatal burns to skin.

Really, other than precursors for more elegant chemicals, it seems like you'd just be asking to burn out your GABA receptors, or NMDA receptors for the stims. Or calcium channels, like a toxic phenibut.

But I'm also pretty high on gabergics right now so I could be typing anything right now.

 

[Jekyl Anhydride]

Od->-nspd

 

[JacksinPA]

I did not include 1-ethynyl-1-cyclohexanol because, as I posted, I only found anectdotal information about it such as the trip report at the start of this thread. I was only interested in established drug molecules where I could find documented biological activity.

Clocental is the allophanate ester of this alcohol. See https://en.wikipedia.org/wiki/Clocental

Carbamates in general are anxiolytic & muscle relaxants. See https://en.wikipedia.org/wiki/Carbamate#Medicine

I'm curious about that 1956 paper but I'm not going to pay Wiley $35 or so to get a copy. I posted those compounds here because I am not sure of their mechanism to create 'severe stimulation' but they sound toxic.

Phenibut I would stay away from after reading some reports & warnings about it. I believe it does the same thing as gabapentin which I have a prescription for & it is apparently not addictive. Both drugs develop tolerance. I would also stay away from 2M2B as its effects seem to linger into the next day likely due to the time needed to metabolize it for excretion.

Here is a link to an interesting paper on methylpentynol (Oblivon) toxicity including hallucinations: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2035981/

 

[Cotcha Yankinov]

gabapentin which I have a prescription for & it is apparently not addictive.

There seems to be a wide range of vulnerability to gabapentin withdrawals, some people occasionally reporting benzo-like withdrawal while others reporting little to nothing. I personally had no issue taking it for months at first and being able to stop without issue, but eventually I began to develop some vulnerability to gabapentin withdrawals (kindling?)

 

[Scrofula]

I was just pointing out the stims are iso alcohols, all the others are tert alcohols.

Iso alocohols get quickly oxidized to ketones in the body, tert alcohols are not metabolized. Seems like a big part of your speculation.

Of the four compounds you listed that were studied as potential drugs, one has a terminal alkyne, which I noticed showing up with selegiline. The stims have interior alkynes.

Selegiline is basically N,N-Ethynyl-methamphetamine, with that ethyne sticking it to MAO forever. I don't think they're things to test out on your brain.


I also noticed how going from OP's reagent to the marketed drugs I mentioned would require use of phosgene. Which is an olde-tyme chemical weapon. Which reminded me that you were last seen (by me) pondering the name of the reaction that occurs when mixing the two precursors immediately before forming VX.

So, when I get tweaked later, rest assured it's just a Homeland marathon for free-Showtime week, and the new chart on my wall connecting VX-> phosgene-> Oblivion -> Miltown -> Wiley -> Placid -> Jack -> Pennsylvania is just that.

 

[JacksinPA]

I take 400-600 mg/day of gabapentin for control of the depression side of bipolar. I've taken 2,000 to 3,000 mg on 3 occasions & got a nice buzz but I was not staging the dosage & I noticed tolerance developing rapidly. But I noticed no overt withdrawal symptoms afterwards & the prescribed maintenance dosage still works OK.

I have more confidence in gabapentin from the CVS pharmacy than I would in buying phenibut on the internet.

 

[Scrofula]

For the record, I get my gabapentin from WalGreen's.

I wasn't implying I thought phenibut was toxic. I meant a person might assume those drugs you mentioned are GABAergic and that they interact with GABA receptors. That's what they hoped with gabapentin but turns out it doesn't even touch GABA receptors, just calcium channels.

I was typing out loud to myself. I know that's hard to believe for many of my fans, who eagerly click my posts in anticipation of another concise, eloquent response, one that's always on-topic; but sometimes I get distracted, too.

 

[Limpet_Chicken]

Are the 'severe stimulant' compounds polyyne long-chain linear aliphatic alcohols by any chance? because that would fit the general SAR for a potent GABAa antagonist. Think cicutoxin from Cicuta virosa, Oenanthetoxin from Oenanthe crocata, carotatoxin from the carrot (presumably a lot less in cultivated varieties), these are all long-chain alcohols bearing multiple triple bonds, and from the looks of it, at least two double bonds, at least in these three, although comparing carotatoxin to oenanthetoxin and cicutoxin (pair of nasty as hell convulsants from water-hemlocks,) it looks like the diol motif of oenanthetoxin and cicutoxin isn't required, and that one -OH group is sufficient for toxicity with that pharmacophore.

And it is known that oenanthetoxin and cicutoxin are capable of skin irritation and transdermal absorption to cause systemic poisoning, even from the plant source certainly in the case of Cicuta spp.

Edit-forgot to mention, in the case of carotatoxin at least, seemingly its also a cannabinoid CB1r inverse agonist, and through a cannabinergic pathway causes irritation and inflammation on dermal contact.

 

[JacksinPA]

I was just pointing out the stims are iso alcohols, all the others are tert alcohols.

The stimulants shown are secondary alcohols, not 'iso' alcohols. No such things.

Ethanol is a primary alcohol. Isopropyl alcohol is a secondary alcohol. Tertiary butyl alcohol is a tertiary alcohol.

 

[JacksinPA]

Are the 'severe stimulant' compounds polyyne long-chain linear aliphatic alcohols by any chance? .

No. The 2 molecules pictured are monoalkynyl carbinols.

 

[Scrofula]

I actually thinks he's on with that plant toxin. It fits too well with those gabergics-gone-lethal.

(and iso-, short for isomer, may not be the best IUPAC here, but with alcohols I think it's understood it means the functional group is at a 2 position. As an isomer of the 2-me. (I mentioned their "secondary"-ness earlier). But I'm going to take that little bit and back away slowly. This thread was as much to play with the naming as anything.

I claim no skill and realized I forgot benzyl v. phenyl a year ago with the tweakers got on with their benzylamines screwing their phenethylamines. (And why would numbering preference switch when those alcohols above turn into ketones? Suddenly everyone counts from the ketone end and not "yne" anymore.))

 

[JacksinPA]

Cicutoxin is an interesting natural product. Very toxic.

OENANTHOTOXIN is also very toxic & apparently very closely related to the previous toxin:

Falcarinol (aka carotatoxin) seems definitely related. Its activity as a toxin helps protect the plants' roots in Nature.

 

[sekio]

Those two are actually positional isomers differing only by the location of a single double bond, the 3d models are very similar.

 

[Scrofula]

Given how nasty storage and handling must be, this could be just the most stable form for characterization.

 

[JacksinPA]

I got my ChemOffice 17 several months ago & only unpacked the ChemDraw application. After consulting with sekio, I today unpacked & installed the Chem3D app. These 2 graphics show the results of my initial trial with cicutoxin. Copying the CD file into Chem3D resulted in the first graphic where the ball & stick 3D model is shown in the left window. This can be rotated via the mouse so the image shown is the one that most closely aligns with the CD structure shown on the right. The second graphic shows the same structure but with a space-filling molecular surface.

 

[sekio]

Don't forget to run an energy minimization on the structure too (Calculations -> MMF94 -> Perform MMF94 Minimization)

 

[Pomzazed]

MM94 takes long time,
But well yes, you need to optimize for lowest energy conformation or the shape may not make sense, since its only draw from geometry (109.5deg for sp3 and 120deg for sp2 centers)

For typical shape, it is ok to use MM2, just use Calculation>MM2>Minimize Energy,
Then tick all choices, and OK.

 

[sekio]

On a reasonably modern computer, MMF94 doesn't take that long (maybe 10-20 seconds), but yes, MM2 is just as effective.