beta ketone analogs

[vecktor]

Digging up an old post here, but I have a quick question or two for anyone who can answer.

If I am reading this correctly, the consensus is that we are not seeing more beta keto substituted PEA's (other than the stimulants and the entactogens) because the synths would be considerably harder (if not impossible?)

I was really trying to find some information on things like beta keto TMA-2, which (at least from the perspective of a novice) would appear to be straightforward. Could bk-TMA-2 not be synthed with TMA-2 as a starting point with some reasonable yield?

Does anyone know if any of these are known and active? (other than the shulgin quote earlier in the thread.) I was afraid perhaps we were not seeing any bk-DOB or bk-2c-B because the ketone did something to destroy HT receptor affinity and they lacked activity.

It would be nice to see a published result somewhere just to know that it was possible. Perhaps one of these days...?

BK 2CB and BK DOB are known creatures both are well down on potency and given the evil cardiovascular effects of beta hydroxy analogues of psychedelic PEA's which would be among their metabolites they are essentially dead. Glennon made them in 2003 from memory.

 

[Dresden]

3,4-methylenedioxycathinone (aka MDC) has also been made synthetically sans enzymes and can be found in a paper on substituted cathinones on erowid. It is active.

bk-TMA-2 is also possible. A special hydrogenation reaction vessel is required in these cases. The reaction that eventually lead to MDC was first published in 1927.

Thank you for not asking me to remember the name of that article. It's on erowid. You can look it up as easily as could I. Plus I've already read it. However, I think the study may have been put out by Glennon.

Hope that helps.

A moi, quiero bk-TMA.

 

[simstimstar]

BK 2CB and BK DOB are known creatures both are well down on potency and given the evil cardiovascular effects of beta hydroxy analogues of psychedelic PEA's which would be among their metabolites they are essentially dead. Glennon made them in 2003 from memory.

Are the keto 2c's more prone to hydroxylation or is the risk of these metabolites the same as with the usual 2c series?

-SimStim

 

[dread]

primary amine beta ketones aren't very stable IIRC...

 

[Dresden]

Primary amine beta ketones are very stable as long as they are stored in their ionic salt form (eg, the hydrochloride form) and away from excess heat, moisture, and light.

(i) substituted propiophenones plus butyl nitrite
(ii) alpha-keto oxime plus special hydrogenation conditions
(ii) viola

It's amazing how ingrained some mythical ideas get stuck in ppl's heads around here.

For example:
1. mdma is a powerful neurotoxin
2. beta-keto primary amines are impossible
3. buphedrone is more potent than methcathinone
4. a testing kit is not only one way but the only way to know if you're getting mdxx
5. mephedrone is pure evil, etc, etc, etc. 8)

 

[vecktor]

Are the keto 2c's more prone to hydroxylation or is the risk of these metabolites the same as with the usual 2c series?

-SimStim

the hydroxy metabolites come from metabolism of the beta keto group so they don't appear with ordinary PEAs

 

[vecktor]

Primary amine beta ketones are very stable as long as they are stored in their ionic salt form (eg, the hydrochloride form) and away from excess heat, moisture, and light.

(i) substituted propiophenones plus butyl nitrite
(ii) alpha-keto oxime plus special hydrogenation conditions
(ii) viola

It's amazing how ingrained some mythical ideas get stuck in ppl's heads around here.

For example:
1. mdma is a powerful neurotoxin
2. beta-keto primary amines are impossible
3. buphedrone is more potent than methcathinone
4. a testing kit is not only one way but the only way to know if you're getting mdxx
5. mephedrone is pure evil, etc, etc, etc. 8)

its much much easier to make them than nitrosation without going into details fc acyclation was how nichols made chiral amphetamines.

It is however true that the beta keto primary amines are very prone to dimerisaton during workup.

beta keto psychedelic PEAs are just a stupid idea IMHO.

 

[simstimstar]

beta keto psychedelic PEAs are just a stupid idea IMHO.

That may very well be I was curious as to whether or not it was possible/if they were active. I am surprised that some of the more unscrupulous vendors haven't been trying to capitalize on the bk versions of more well known PEAs (sounds like a good thing they aren't, if they are cardiotoxic). So it must be the extra difficulty required in synthing that is stopping them (we know they probably don't really care if people are blowing up their hearts).

Thanks for the responses, something to think about. I will continue to search for some info about the aforementioned bk-2cb and bk-dob as I would still like to read some more in depth about these bk pea's. Reminds me of Denis Leary's "No Cure for Cancer" when he is talking about how it's getting so that the legal drugs are worse than the illegal ones (his comment was about NyQuil (dxm) but is relevant).

Cheers,
-SimStim

 

[/navarone/]

I wonder why i've never seen a beta ketone analogue of methyphenidate. Would it actually be stronger as a DA-NARI?

 

[simstimstar]

I wonder why i've never seen a beta ketone analogue of methyphenidate. Would it actually be stronger as a DA-NARI?

Correct me if I am wrong here, but I am pretty sure you will never see a beta keto methylphenidate, because methylphenidate already has an acetate group in the beta position.

Replacing the acetate with a keto group would give you bk-BZP which is likely a stimulant. Maybe even a really nasty one at that.

This is off topic but slightly related to the last post, is 3,4-methylenedioxy-methylphenidate a known compound? Does it have any activity? (distracted, sorry)

 

[/navarone/]

You got a bit confused.

BenZylPipepazine is this:

Methylphenidate is this:

I was thinking of a beta keto analogue of benzylpiperidine:

 

[simstimstar]

^^^^^^^

Oooops! I forgot a nitrogen (and position)

My (under)educated guess is beta-keto-2-benzylpiperidine (bk-2-BP) would be more potent than 2-benzylpiperidine (2-BP) and less potent than methylphenidate(MPH).

Anyone else care to weigh in on it?

 

[hamhurricane]

phenyl-piperidin-2-ylmethanone/bk-2-Benzylpiperidine - yes i often wondered about this chem, i could actually see it being really nice given the similarity to MPH, can't find any info on its pharmacology though no assays linked off pubchem

 

[/navarone/]

Maybe it has been synthetized before but probably the pharmaceutical companied decided to switch it with an ester to reduce balance DA-NE RI for a mmore specific ADHD pharmaceutical,
Probably MPH might also be less toxic but in my opinion it should be a stronger stimulant.

2-BP is 20 times less potent than MPH but it boosts Ne levels to to the same extent as dextroamphetamine.

4-Benzylpiperidine is also very interesting since it's both a monoamine realeasing agent (with a 20 fold selectivity towards dopamine than serotonin) and it also acts as a MAOI, Especially for MAO-A.