Idea: 1-phenethylurea and related chemicals

[Stupid_human]

The title sums it up. Could phenethylurea (Or more importantly, phenethylurea derivatives) be worth looking into? I can't find any info that would indicate it's been looked at in this manner, but given it's obvious structural similarities to phenethylamine it seems like it could be worth looking into. 1-phenethylurea itself is unlikely to be interesting even if it is active, but substitutions on the benzene ring like those on the interesting phenethylamines could be better, for example 1-(3,4,5-trimethoxyphenethyl)urea.

I don't know if these compounds would actually be synthetically viable, and the extent to which we can discuss that here is limited, but if they could be made, do you think they'd be worth looking into?

 

[d1nach]

Why reinvent the wheel? I couldn't find anything on Google so even if I could make it I wouldn't touch it with a ten foot pole.

 

[Stupid_human]

Why reinvent the wheel? I couldn't find anything on Google so even if I could make it I wouldn't touch it with a ten foot pole.

To learn something new about the chemistry of phenethylamine drugs, and about the chemistry of the brain in general? To potentially, eventually, get a drug that improves in some way on the existing ones, or that is active in a new way? I mean, if we all followed that logic of "We've already got something that works fine, why keep working?", we wouldn't have anywhere near the level of technology or scientific understanding we have today.

Besides, it's not reinventing the wheel. It has basis in the phenethylamines, so it's more like trying to make a better type of wheel.

But certainly, I'm not suggesting you or anyone should just jump immediately in to taking something nobody's explored before. Start with some toxicity tests; it can't be too hard at all to get your hands on a few rats. After it's clear it's at least not immediately killing the rats, someone braver than you or I could test it.

 

[d1nach]

Heh have you heard of Alexander shuligun he has a book pihkal that might be what your looking for

 

[Limpet_Chicken]

These carbamates are more likely to be GABAergic types. Ethylurea (urethane) is used as an animal anaesthetic in research, although no longer in humans due to its being carcinogenic. I would expect phenethylurea to be active, but I would avoid it until at least doing an Ames test to examine it for potential to damage DNA as a mutagen/carcinogen.

https://en.wikipedia.org/wiki/Ethyl_carbamate

Probably a very long acting sedative-hypnotic. But not sure as it would be particularly a healthy one to ingest in practice. Some carbamates, such as meprobamate are used occasionally these days, although indications in the UK in the BNF are 'less suitable for prescribing'

Have had methocarbamol myself, the carbamate of guiafenesin, and it was utter shite. Some of the carbamate sedative-hypnotics are reported to be very abusable, some, such as methocarbamol are utter, abject garbage.

 

[serotonin2A]

These compounds would not work the way you want them to because the nitrogen is not very basic. So they wouldn't work as analogs of existing stimulants, hallucinogens, or entactogens.

 

[Stupid_human]

Heh have you heard of Alexander shuligun he has a book pihkal that might be what your looking for

Of course I've read PiHKAL. I certainly wouldn't have posted about a new idea without checking if Shulgin had tried it first. But phenethylurea derivatives were not among the phenethylamine derivatives that he tried.

These carbamates are more likely to be GABAergic types. Ethylurea (urethane) is used as an animal anaesthetic in research, although no longer in humans due to its being carcinogenic. I would expect phenethylurea to be active, but I would avoid it until at least doing an Ames test to examine it for potential to damage DNA as a mutagen/carcinogen.

https://en.wikipedia.org/wiki/Ethyl_carbamate

Probably a very long acting sedative-hypnotic. But not sure as it would be particularly a healthy one to ingest in practice. Some carbamates, such as meprobamate are used occasionally these days, although indications in the UK in the BNF are 'less suitable for prescribing'

Have had methocarbamol myself, the carbamate of guiafenesin, and it was utter shite. Some of the carbamate sedative-hypnotics are reported to be very abusable, some, such as methocarbamol are utter, abject garbage.

I see, thank you for the warning about the potential carcinogenicity. But you might want to take another look at the structure; ethyl carbamate is not the same chemical as ethylurea, though they are similar in structure. It's quite possible phenethylurea will be a sedative due to the structural similarity, but it's also different enough that it's quite possible it won't be.

I wonder if the serotonergic properties of the psychedelic phenethylamines are necessarily linked to their stimulant properties. If phenethylurea did end up as a sedative, could you still end up with a psychedelic by substituting it with the mescaline pattern, but end up with a psychedelic that is also a downer?

 

[Limpet_Chicken]

Sorry, didn't mean to say urea. I meant, urethane. The common name for ethyl carbamate, which is indeed a sedative-hypnotic. I believe, of a more barbiturate-like action than benzo-like, which seems to be the way with the sedative-hypnotic carbamates.

 

[sekio]

I bet PEA-ureas would be cleaved to the PEAs in vivo.

ha ha, PEA and urea, toilet-amine.

 

[Limpet_Chicken]

Do I smell a pro-drug in the offing? Although I'd still expect something like phenethyl-urethane to be likely a GABAergic.

But as I said, I'd want to perform an Ames test first to see if its likely carcinogenic.

 

[sekio]

Addendum: I like methocarbamol. It's a nice muscle relaxer with few side effects.

 

[serotonin2A]

Do I smell a pro-drug in the offing? Although I'd still expect something like phenethyl-urethane to be likely a GABAergic.

But as I said, I'd want to perform an Ames test first to see if its likely carcinogenic.

It would be a prodrug for a metabolite that would not be a GABAergic drug.

It is a really bad strategy either way. If you pursue these as GABAergics and they are metabolized rather quickly to stimulants, then you have would have to continually redose to maintain sedative effects, which would cause blood levels of the stimulant metabolite to build up over time.

On the other hand, if you pursue this as a stimulant that happens to initially produce sedative effects, then you will be continually ingesting a short-duration GABAergic PAM -- sedative-hypnotics that are notoriously the most likely to produce dependence. Plus the sedative-hypnotic use would be driven by the reinforcing properties of the stimulant metabolite, which is a recipe for severe dependence.

Prodrugs can be useful but generally you want the prodrug itself to be inactive (or to mimic the metabolite) to avoid these types of problems.

 

[aced126]

These compounds would not work the way you want them to because the nitrogen is not very basic. So they wouldn't work as analogs of existing stimulants, hallucinogens, or entactogens.

True.

On the other hand, changing carbamide to guanidine functionality might do something, and this is always something I have been curious about.

 

[Limpet_Chicken]

I was thinking more along the line of using it, if used at all, for a psychedelic of relatively lesser potency, and forming an analog of one of the more potent carbamates. Kind of like the idea I've been mulling over for some time, about making the MDxx 1-ethynylcyclohexanol carbamate. The main active drug being the psychedelic or stimulant, and rather than taken regularly for GABAergic effects, the idea being to slow absorption somewhat and provide a hint of sedating effect so as to smooth the comeup out, even off any rough edges, so to speak.