Ketamine salts solubility

[Rectify]

Looks disappointing.

 

[Fertile]

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Plain phenylmorphones are questionable. I think that the methyl is required for the same reason it's required in AMPhEtamine (alpha methyl phenylethylamine), to prevent monoamine oxidation. Long ago someone reported on having tried it and they concluded that any perceived activity was a placebo.

Now if you find appropriate ring-substitution of the aromatic, this seems to prevent MAO from destroying it. You should look at the metabolism of fenfluramine. I'm guessing that the 3-fluoro phenmetrazine was based on the fact that a meta F or TFM seems to stop MAO. But if you read about fenfluramine, you will see it caused quite some fallout.

 

[simstim]

There is this flumexadol that I found was the reason why I thought a 2c substitution pattern might work.

Flumexadol is the phenylmorpholine of fenfluramine.

 

[simstim]

Oxaflozane is its pro drug probably for time release. Interesting that wiki says anti-cholinergic in high doses so perhaps that's why 2-phenylmorpholine is sedative?

 

[Fertile]

Ah, OK. So the meta-TFM does stop the MAOs as I suggested. Similarly fludorex proves fastandbulbouses point that just a fragment of the morpholine ring will allow for 2-carbon amines to be active stimulants. It also suggests why the meta-TFM derivative of benzylpiperazine was produced.

BUT you need to remember that the meta TFM moiety has produced a LOT of compounds that tuned out to have 5HT2b affinity. THATS BAD.

Examples of the meta TFM being swapped for a plain F seem to be known for all these compounds.

It would be interesting to take that 3-methyl moiety from 3-fluoro phenmetrazine. You instantly remove a stereocenter and the active isomer can be resolved quite easily. Yes, it would be more work and no, you cannot do anything with the inactive isomer BUT you will, at a stroke, halve the amount of material in a dose and that can only be a good thing.

As a rule of thumb, if you have the option of placing a -CF3 an -F or a -CH3 on a ring, always test the latter FIRST. I can find no example in which a para or meta methyl ring-substitution has increased toxicity. The -CH3 also acts as a sacrificial moiety i.e. the body will metabolise the material via that methyl in 3 steps. -CH3 --> -CH2OH --> C(O)OH --> C(O)ONa.

I very much like this as one can be confident in knowing that no toxic metabolites will be formed.

 

[simstim]

Ah, OK. So the meta-TFM does stop the MAOs as I suggested. Similarly fludorex proves fastandbulbouses point that just a fragment of the morpholine ring will allow for 2-carbon amines to be active stimulants. It also suggests why the meta-TFM derivative of benzylpiperazine was produced.

BUT you need to remember that the meta TFM moiety has produced a LOT of compounds that tuned out to have 5HT2b affinity. THATS BAD.

Examples of the meta TFM being swapped for a plain F seem to be known for all these compounds.

It would be interesting to take that 3-methyl moiety from 3-fluoro phenmetrazine. You instantly remove a stereocenter and the active isomer can be resolved quite easily. Yes, it would be more work and no, you cannot do anything with the inactive isomer BUT you will, at a stroke, halve the amount of material in a dose and that can only be a good thing.

As a rule of thumb, if you have the option of placing a -CF3 an -F or a -CH3 on a ring, always test the latter FIRST. I can find no example in which a para or meta methyl ring-substitution has increased toxicity. The -CH3 also acts as a sacrificial moiety i.e. the body will metabolise the material via that methyl in 3 steps. -CH3 --> -CH2OH --> C(O)OH --> C(O)ONa.

I very much like this as one can be confident in knowing that no toxic metabolites will be formed.

People have died from amphetamine that had added para methyl amphetamine mixed in it.

Also, 4,4'-DMAR.

 

[Fertile]

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Even earlier today I would have been skeptical of the compound above being active but someone brought in a good reference. Fastandbulbous had sampled some compounds with methyl ethers and stated they worked and I know Shulgin did test what seemed a surprising number of them (the BO series).

So it seems that for the BO series, ring substitution of 2,5-dimethoxy-4-<something> and 3,4-MD & good old 3,4,5-trimethoxy all work. I think that's excellent work. Not my work, I hasten to add.

 

[4meSM]

Many monoterpenoids, which are mostly hydrocarbons (with one or multiple double bonds) and an hydroxy group, have been described as being centrally active (usually as mild sedatives).
I wonder if some of them could be turned into “recreational” drugs by replacing the oxygen with an amino group. Another possibility would be to introduce an ester group containing an amine somewhere in the chain. The nitrogen would also make them a bit more hydrosoluble which might increase their bioavailability (which is one of their main issues).

Does someone have some kind of insight about that ? Aminoterpenes are extremely rare in nature and artificial derivatives haven’t been studied much as far as I know, although there are studies that show that certain derivatives could potentially be used to treat some neurological conditions/disorders.
I’ll try add some references later.

 

[Fertile]

I would've called it mescaketobenzylpiperidine myself.

I think without ring substitution a few people have suggested that it would likely make a good stimulant, but oddly for what seems such a simple compound, the routes to it are unexpectedly hard.

If one could buy the precursor to levophacetoperane (the bare hydroxyl) then it would be simple. Sadly levophacetoperane hasn't been made in a long time.

As the amine is secondary, it will not have amazing 5HT2a affinity. DMBMPP is a couple of orders less than 25B-NBOMe, for example. BOM in Pihkal appears to be a better target. I may be overstating this BO class today because someone pointed out that they were pretty active and a couple of days ago fastandbulbous vouchedsafed that stimulant with that methyl ether were pretty darn active.

 

[izo]

Well diclofensine doesn't have the aromatic amine. The

i meant nomifensine. could have guessed that also. sometimes i wonder if you even have a bachelor...

 

[Fertile]

With the nomifensine/diclofensine I certainly did provide reference. I pointed out that only 1 homologue had said aromatic amine and I gave the reference to the specific patent. I did refer to the class at all times. The index patent I provided doesn't have the suspect moiety and the other examples show it isn't a requirement.

 

[izo]

want to try diclofensine and sertraline some time. nomifensine, why not but not that relevant.

 

[Fertile]

Well they are all very similar in their action. Diclofensine is a triple reuptake inhibitor, nomifensine is DAT/NET selective. As I noted, it's possible to modify it's reuptake activity for each monoamine using the meta and para positions of the benzene with the ethylamine moiety. I think I put up an image showing that one.

Evidently they put in a lot of work to find a way to alter selectivity without that aromatic amine.

As I said, 2 guys tried the stuff by taking several doses in a day and gave a precis of their comments.

It does make me wonder just what on earth that aromatic amine IS doing. As I did note, in the original patent, the amine is secondary. No N-methyl. So, from the patents, it becomes apparent that the actives do not actually have a long T½. The medicines are actually prodrugs. I appreciate that later they did design compounds with tertiary amines that WERE active but they had vastly increased affinity for the monoamine transports.

It's a really elegant design path from amphetamine to pipradrol to nomifensine/diclofensine class to the McN & JWJ offerings. But every single time they never quite reach market. Maybe this shows us that rational design really will fall to in silico HTS? A sad day, but you cannot go against science.

 

[izo]

Any comment on atomoxetine? Tried fluoxetine and citalopram, almost indistinguishable in its effects. Good stuff, strong euphoria from one standard dose.

 

[atara]

People have died from amphetamine that had added para methyl amphetamine mixed in it.

Also, 4,4'-DMAR.

Indeed, this compound seems to have some resemblance to PMA. The initial hydroxylation of toluene is slow, slow enough that ring epoxidation is a competing pathway, which is responsible for the hepatotoxicity of toluene.

https://journals.sagepub.com/doi/pdf/10.1177/0269881113487950

 

[Fertile]

I have the paper. I didn't realise that the p-Me would form an epoxide. I had presumed it required pretty strong oxidants since 30% H2O2, peroxoacids or m-CPBA had to be used. We did come across a few deaths. p-TAP mixed with amphetamine sold as MDA.

 

[Mom's Spaghetti]

Anyone seen this chemical? 3d-mxe
It's being sold by china

 

[Skorpio]

Anyone seen this chemical? 3d-mxe
It's being sold by china

I've always heard 3DMXE was the deoxy form, not the deurterated form.

Deoxymethoxetamine - Wikipedia

en.m.wikipedia.org

If real, very intriguing.

Edit: Deuterations are cool because they typically don't alter binding affinity too much, but do reduce the ability for that site to be oxidized. At best you can deuterate a specific site and enhance the duration by decreasing metabolism without changing the pharmacodynamics too much. At worst you get a me-too drug with similar kinetics and dynamics, so would be pretty cool.

 

[Mom's Spaghetti]

Yeah I've heard DMXE called that as well but this is supposedly 3 duterations added to mxe

 

[izo]

mmmm I like deuterium

drinking too much D2O is toxic, btw. slows down the metabolism. and it tastes kinda sweet. fyi.