• N&PD Moderators: Skorpio | thegreenhand

Alcohol-like

How about putting three chlorines on a methyl group in 2M2B? There's two different methyls where that can be done. Is the effectiveness of 1,1,1-TCE much greater than that of ethanol just because of the higher lipid solubility

Edit: Sorry for the wrong numbering, it is 2,2,2-trichloroethanol... I associated it in my mind to the anesthetic 1,1,1-trichloroethane, which caused that misnumbering.
 
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How about putting three chlorines on a methyl group in 2M2B? There's two different methyls where that can be done. Is the effectiveness of 1,1,1-TCE much greater than that of ethanol just because of the higher lipid solubility

If you want stronger, there is a huge range of solvents that are or were used as general anesthetics over the decades. AFAIK things like sulfonmethane aren't controlled but they aren't fun.

It would appear to be the case that only ethchlorvynol and ethanol produced an associate of recreational users. Make of that what you will. I'm still waiting to find out why Almorexant is a CIII drug in the US.
 
I was just theoretically interested in the possibility of 2-trichloromethyl-2-butanol having a shorter duration of effects than chlorbutanol with its notorious 2 week half life... Also, it would be a chiral molecule, allowing the testing of how the subjective effects would depend on stereochemistry.
 
A trichloromethyl group behaves similar to a halogen in a leaving group aspects,
Having both CCl3 and OH on the same carbon may not be so stable?
Maybe decomposed back to a chloroform and an MEK (starting mat for them)
 
I think you might do better looking closely at the law governing chloral hydrate. 2,2,2-trichloroethanol is the active (metabolized by alcohol dehydrogenase) but I don't think trichloroethanol IS controlled. Forming the hydrate is verboten BUT thanks to that old time chemistry:

US Patent 425039 - Chloralformamide
DE Patent 234741 - Chloralacetamide
DE Patent 498432 - Dichloralurea

Now that's 1890s chemistry right there.

For my money I would take a good look at 2,2,2-trichloro-1-hydroxyethyl carbamate

It's got the halide, it's got the hydroxy and it's got the carbamate.


All things considered, I would read this first https://doi.org/10.1016/j.cdc.2018.04.002

To me chloral hydrate falls into the same category as things like quetiapine, gabapentin & amitriptyline. I know people abuse them and I even know people who will pay for the privilege but outside of prisons and secure psychiatric units, just WHO is reduced to abusing stuff like this? I place 2-methylbutan-2-ol in the same bin although I admit that the carbamate is interesting. What is vastly more interesting is 2-methylbut-3-yn-2-yl carbamate. Actually, almost all of the low MW tertiary alcohols have been tested as sedative/hypnotics and the defining feature of them all is a small TI, sudden unexplained deaths and the people working on the production-lines going loopy. I don't mean TEL 'loony gas'/house of butterflies mad- but I mean people ending up in hospital (if they were lucky).

Why not go with something a bit more euphoric. Nitromethaqualone looked like a bad choice from day 1 but buried in the patent is a NON-mutagenic analogue that is actually more potent. Example 12 looks good and for the real QSAR nerds, swapping the 2-methyl for a 2-fluoromethyl increases potency by an order of magnitude. The proof of the cake and all that but a 714 mimic with just 2.5mg of active and a 50-50 caffeine/paracetamol filler/binder so it smokes clean right off the foil!

In full disclosure, it's not overly complex to manipulate a 1,4-benzo to produce subjective effects indistinguishable from the original but with fluoronitroqualone out of the bag, the benzo is actually LESS potent (and a lot harder to synth). All I can tell you is that nitrobenzodiazepines have serotonergic activity (which is why they ended up as hypnotics) so if you excise the a1 affinity (all the Z-drugs are a1 selective) then you are left with something midway between MDMA and diazepam. You love everyone and you can speak slowly in a level tone when describing the sexual experiment you want to carry out... regrets... but too few to mention.
 
What do you mean about people on the production lines? something like exposure to the vapors and unsuspectingly, building up a tolerance and ending up in a DTs-like state?

I'd be careful with methaqualone analogs that are untested, methylmethaqualone could have been a disaster from everything I've read of it. IIRC, doesn't it have some activity as an agonist of AMPA type glutamate receptors? the overdose effects profile for methaqualone itself is quite unusual for a GABAa potentiator, with overdoses resulting in seizure, motor hyperreflexia and hypertonia, which is IMO suggestive of an underlying excitatory effect of some nature, there are quite a few competitive ANTagonists at this site known among quinazolinone derivatives related to methaqualone, its just a nasty thought in the back of my mind with hitherto-untested derivatives, granted potent GABAa agonist effects would help mitigate damage, but say something turns out to be of low potency at GABAa and either full or partial agonist at AMPARs....its the kind of fuck-up that seems logically possible, especially given the effects methylmethaqualone had on people, and nonfatal excitotoxic neurological insult often is slow to heal, if it ever does. Just seems like rather more room for potentially lifelong disability than is good.

Look at what the likes of domoic acid, and the acromelic acids do (granted the latter is a kainate receptor agonist, but the effects are still extremely prolonged, years not infrequently in cases of mycotoxicosis due to Clitocybe acromelalga and C.amnoelens), and cases of amnesic shellfish poisoning due to domoic acid can cause permanent damage.

As for a low TI, it seems to be rather par for the course with alcohol-mimetics, the only reason it isn't so with ethanol is due IMO to the rather low weight potency, and quantity one needs to imbibe before frank alcohol poisoning develops.

Hell most GABAa agonists don't really have much tolerance for people being stupid with them, benzos seem to be the exception rather than the rule, still, a low TI, IMO doesn't rule it out as potentially recreational,it just means one has to be careful with it (not withstanding the occasional nasty additional toxic effects of certain GABAergics, such as the antiglucocorticoid effects of glutethimide, or the capacity of ethchlorvynol to cause severe or even fatal lung injury if injected, and a few hair-trigger individuals like propofol). Just look at for example, chlormethiazole, its pretty notorious for it's toxicity in overdose, still has a useful place in medicine for alcohol detox (it apparently inhibits alcohol dehydrogenase, unlike other GABAergics), and as a very rapid-acting oral antiseizure drug (it isn't actually licensed in the UK as an anticonvulsant, but I've never found anything better. No physical dependence after several years of use TDS. Works within minutes, and as recreational GABA-modulator type drugs go, IMO its one of the better ones by far, although quite good at killing people in overdose, too. Moral of that? be careful with depressants with a very low TI.

I can't imagine chloral hydrate is good for people, either, I'd guess it's hepatotoxic, it's relative chlorobutanol certainly is. And it is hell on the stomach too. And just in case anyone is wondering, changing the halogen from Cl to Br, apparently makes it even worse. Some old medical books from the 1700s I have briefly summarize it, and in no uncertain terms condemn it to the garbage heap, apparently it is horrendous on the GI tract, to the point they wouldn't even use it in those days, the same time as the british pharmacopoeia included such things as HCN, arsenic, Sb, Hg, Pb and all manner of seriously dubious plant remedies, such as Aconitum and Veratrum.

Edit-Polymath..I certainly see your point, I take people to account for using the likes of 'retard' 'spastic' etc/ as a perjorative. Cretin..these days not so much, 'idiot' 'imbecile' 'moron' and 'cretin' were all in use as medical diagnoses, to denote degrees of mental retardation, with cretinism of course being due a more specific cause, but IMO times have changed, and so has general speech, it isn't actually still used as a medical diagnostic label is it? might have been current a century or two ago, but not now.

I doubt it gets used much if at all as a put-down aimed at those who experienced a childhood iodine deficiency, the term itself, dates back from when 'idiot' 'moron' and 'imbecile' were used as actual diagnoses, and in this day and age, nobody is going to be likely to take someone using those terms as insulting people with MR. And, not that you'd know, not knowing me personally, but I'll be the last person you are likely to find on BL attacking such people. Actually, I very seldom meet any NT females I'd find attractive, I can count two, maybe three people (albeit one was a psycho bitch from hell, definitely something wrong with the fucker anyway, but not in a special needs kind of way) I've ever been with who weren't special ed of some description. Got nothing against people with mental retardation at all, and besides, I'm classically autistic myself, so such pejorative use would be rather an own goal, no?
 
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I can't imagine chloral hydrate is good for people, either, I'd guess it's hepatotoxic, it's relative chlorobutanol certainly is. And it is hell on the stomach too. And just in case anyone is wondering, changing the halogen from Cl to Br, apparently makes it even worse. Some old medical books from the 1700s I have briefly summarize it, and in no uncertain terms condemn it to the garbage heap, apparently it is horrendous on the GI tract, to the point they wouldn't even use it in those days, the same time as the british pharmacopoeia included such things as HCN, arsenic, Sb, Hg, Pb and all manner of seriously dubious plant remedies, such as Aconitum and Veratrum.

Edit-Polymath..I certainly see your point, I take people to account for using the likes of 'retard' 'spastic' etc/ as a perjorative. Cretin..these days not so much, 'idiot' 'imbecile' 'moron' and 'cretin' were all in use as medical diagnoses, to denote degrees of mental retardation, with cretinism of course being due a more specific cause, but IMO times have changed, and so has general speech, it isn't actually still used as a medical diagnostic label is it? might have been current a century or two ago, but not now.

I doubt it gets used much if at all as a put-down aimed at those who experienced a childhood iodine deficiency, the term itself, dates back from when 'idiot' 'moron' and 'imbecile' were used as actual diagnoses, and in this day and age, nobody is going to be likely to take someone using those terms as insulting people with MR. And, not that you'd know, not knowing me personally, but I'll be the last person you are likely to find on BL attacking such people. Actually, I very seldom meet any NT females I'd find attractive, I can count two, maybe three people (albeit one was a psycho bitch from hell, definitely something wrong with the fucker anyway, but not in a special needs kind of way) I've ever been with who weren't special ed of some description. Got nothing against people with mental retardation at all, and besides, I'm classically autistic myself, so such pejorative use would be rather an own goal, no?

The interesting theoretical question about trichloroethanol or chlorbutanol is that they seem to just be more lipophilic versions of small-molecule alcohols, but have an effectiveness by gram that is even greater than you would expect just on the basis of the lipid solubility. Of course, there are also other expections among similar compounds, such as the chlorofluorocarbons that have an especially large number of fluorine atoms in them and act as strychnine-like convulsants instead of being CNS depressants and anaesthetics. I agree that the chloral like compounds have no actual use today.

I really didn't take that cretin thing seriously, it was more like a comment "hey don't mock cretins by comparing them to drug war fanatics". The idea of someone getting left physically and mentally to the level of a small child because his/her parents couldn't afford thyroid medications is just exceptionally cruel even among other disabilities.
 
Well maybe chloral hydrate itself might just have use still. IIRC it is one of the only GABAa agonist/PAMs that does not suppress epileptiform spike-and-wave discharges. Could make it useful for conscious sedation in diagnostic settings when kids need to undergo say, MRI or PET scanning, in diagnosis or follow-up work in seizure patients.

And chloral is still used in Melzer's reagent, one of the fundamental chemical test reagents for mycologists, to determine amyloid vs inamyloid vs dextrinoid colorimetric character of fungal spores in aiding identification for either professional mycologists or those who are very into their mushroom foraging (guilty as charged)

And I didn't think you had, hell, it'd be fair enough for a convicted child rapist to sue for defamation of character if used for such a comparison, one way or the other, SOMEONE is going to come out of it looking like a bastard if used for such a metaphor. As for the historical etymology of 'cretin', one fairly common explanation is that it originated as a contraction of 'chretienne' [sp?], french meaning 'christian', I.e in such times 'still christian=still a human being'
 
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