beta ketone analogs

[slopoke]

I was just pondering, there are several BK-XXXX type chemicals out there; i was judt wondering in bk-mda has been explored?

Going with the way methylone was similar to mdma, just not as strong and long lasting, could it be possible that BK-MDA would follow along the same lines, because that could be a very nice experience...

Is it even possible, would it be stable etc

Thanks

 

[bigmac74]

I thought I remembered reading something by Shulgin mentioning that beta-ketone amphetamines were only stable enough to be ingested if they had a secondary amine (or something along those lines).

If true, then MDA wouldn't work.

 

[fastandbulbous]

Beta-ketone primary amines are stable, but only when in salt form (ie while in protonated ammonium form), or else cathinone wouldn't exist at all. When it comes to getting to them via a synthetic route that's not involving enzymes (like cathinone), then at some point it's almost inevitable that you'll need to do an acid/base extraction, involving the substituted cathinone in alkaline soln; as a result, you end up with the diamer formation (ie. you're fucked!).

If true, then MDA wouldn't work.

Actually, none of the psychedelic amphetamines or phenethylamines would work

See attached jpeg

 

[hussness]

does dimerization happen to an appreciable extent with an A/B extraction involving a beta-ketone secondary amine?

 

[specialspack]

Beta-ketone primary amines are stable, but only when in salt form (ie while in protonated ammonium form), or else cathinone wouldn't exist at all. When it comes to getting to them via a synthetic route that's not involving enzymes (like cathinone), then at some point it's almost inevitable that you'll need to do an acid/base extraction, involving the substituted cathinone in alkaline soln; as a result, you end up with the diamer formation (ie. you're fucked!).



Actually, none of the psychedelic amphetamines or phenethylamines would work

See attached jpeg

How is it that methylone is synthezised then?

In Basel, Shulgin said that he'd tasted most of the BK analogues of PEAs, and they were mostly all active at around the same levels.

 

[Morninggloryseed]

Methylone is a secondary amine. But the MDA and CO family is an exception to the rule....all of the other psychedelic phenethylamines and CO loose their activity when you start adding carbons to the amine. Well I shouldn't say all, but the ones that have been made....they become inactive when you start adding carbons.

 

[djfriendly]

I too have long wondered why whoever it was that decided to market bk-MDEA and bk-MBDB never produced bk-MDA. Thanks for the explanation.

 

[specialspack]

Methylone is a secondary amine. But the MDA and CO family is an exception to the rule....all of the other psychedelic phenethylamines and CO loose their activity when you start adding carbons to the amine. Well I shouldn't say all, but the ones that have been made....they become inactive when you start adding carbons.

Doh.. thanks MGS, sorry f&b for not reading properly!

if Shulgin claims to have tried the beta-keto analogues of what are all primary amines, then their synthesis must be possible, no?

 

[fastandbulbous]

^ Yes, but it'll be a right fanny-on having to modify the synthesis to prevent that. Alternatively, I suppose you could carry out an acid catalysed hydrolysis of the diamer as it's just a cyclic Schiff type base, but I'd bet it chance to be somewhat unstable (possibly through absorbtion of atmospheric moisture by the salt etc).

When it comes down to it, it'll be an awkward synthesis and chance to require much more stringent storage conditions (like under a dry nitrogen atmosphere) to prevent it 'going off'. If you remember, cathinone in the leaves/shoot tips of Catha edulis (khat, qat etc) is only viable for 24-36 hours after picking. Beyond that it's converted into norpsuedoephedrine.

Personally, I'd have thought the beta-methoxy (equivalent to reducing the keto group and O-methylating the resulting hydroxy group) is a far better bet - it's stable, it's not controlled (well at least not in the UK, other than BOD & BOB - the beta methoxy 2C-D and 2C-B respectively) and is nearly twice the potency of the unsubstituted phenethylamine chain

 

[specialspack]

Well hopefully some of this will be covered in the new book, the Psychedelic index. Althought I can't remember if it's going to included synthesis routes..

 

[djfriendly]

^ Yes, and yes.

 

[Morninggloryseed]

Personally, I'd have thought the beta-methoxy (equivalent to reducing the keto group and O-methylating the resulting hydroxy group) is a far better bet - it's stable, it's not controlled (well at least not in the UK, other than BOD & BOB

Personally, I'd have thought the beta-methoxy (equivalent to reducing the keto group and O-methylating the resulting hydroxy group) is a far better bet - it's stable, it's not controlled (well at least not in the UK, other than BOD & BOB

Thought about using in what capacity? From the sound of what is in PIHKAL, the beta-methoxy analogues do not sound very pleasant. Potency increase or not.

How about the phenylbutenamine and phenylpropenamine analogues that you theorized about before? These sound delightfully interesting.

In Basel, Shulgin said that he'd tasted most of the BK analogues of PEAs, and they were mostly all active at around the same levels.

Man, now I really wish I had some sort of transcript. Could you please fill us in with more detail? Did he mention anything more than he just tried them and they were of the same potency.

I must say, based on how methylone, ethylone, and CO compare to their respective phenylethyl and phenylpropyl homologues, the cathinone psychedelic would seem delightful. It is too bad they are so difficult to produce because I would bet a few are phenomenal.

 

[specialspack]

Man, now I really wish I had some sort of transcript. Could you please fill us in with more detail? Did he mention anything more than he just tried them and they were of the same potency.

Fraid I can't tell you more - that was literally all he said - "I've made and tasted most of the beta-ketone analogues, and most of them were active at similar levels to their original counterparts". It was part of the "ask the Shulgins" session, and I can't recall now what the question was, if it was about the b-k's or if he was using it to illustrate another point.

Have to say you didnt miss that much in that session though - that was about the only worthwhile thing that was said - most of it was taken up with some idiot ranting about Dune and taking MDMA when you're pregnant. 8( The fact that it was consecutive translation between English and German made things worse - everyone was talking at cross purposes.

PS - am I being stupid - what's CO?

 

[Morninggloryseed]

Sorry....MDA and COmpany. As in the MDA family as in a psychedelic/entactogen with a methylendioxyphenylethylamine as its chemical "skeleton." It could also mean Colorado, my home state. But I meant the former.

 

[fastandbulbous]

Thought about using in what capacity? From the sound of what is in PIHKAL, the beta-methoxy analogues do not sound very pleasant. Potency increase or not.

The beta-hydroxy sounded unpleasant (for effects on b.p.), but the beta-methoxy sounded like a mixed bag - there may well be some 'good ones' among the whole series.

How about the phenylbutenamine and phenylpropenamine analogues that you theorized about before? These sound delightfully interesting.

I know! It's just that there doesn't appear to be an established synthetic route for them, so it'll require somebody with a feel for synthetic organic chemistry like Shulgin to establish a practical route to them (while I might understand the reaction mechanisms required, my practical skills for such are not wonderful - or even adequate - for such a thing; even if I were foolhardy enough to consider doing it!). I'm just hoping that somebody, somewhere with the needed skill decides that it's interesting enough to investigate - and then publishes the results.

At that sort of level, you stick to what you understand and are competent at - & for me that's receptor conformations and SAR studies!

 

[cynosure]

^ Yes, but it'll be a right fanny-on having to modify the synthesis to prevent that. Alternatively, I suppose you could carry out an acid catalysed hydrolysis of the diamer as it's just a cyclic Schiff type base, but I'd bet it chance to be somewhat unstable (possibly through absorbtion of atmospheric moisture by the salt etc).

When it comes down to it, it'll be an awkward synthesis and chance to require much more stringent storage conditions (like under a dry nitrogen atmosphere) to prevent it 'going off'. If you remember, cathinone in the leaves/shoot tips of Catha edulis (khat, qat etc) is only viable for 24-36 hours after picking. Beyond that it's converted into norpsuedoephedrine.

Personally, I'd have thought the beta-methoxy (equivalent to reducing the keto group and O-methylating the resulting hydroxy group) is a far better bet - it's stable, it's not controlled (well at least not in the UK, other than BOD & BOB - the beta methoxy 2C-D and 2C-B respectively) and is nearly twice the potency of the unsubstituted phenethylamine chain

Yes, methcathinone and cathinone are stable as the HCl salts, but are even stable for reasonable amounts of time in certain solvents. Chloroform and dichloromethane seem to be two solvents where reactivity of the nitrogen and carbonyl carbon DON'T seem to being a problem.
The cathinone synths that are on Rhodium are outdated and were never that good. There are probably a number of routes that would lead to much higher yields, but then it may not be kitchen chemistry any more. For one, the Jones oxidation is probably not the best choice. And if you really wanted to avoid cyclization, you could always N-Boc protect your starting material (N-Cbz would probably be better). But that's besides the point, there's no reason that the beta-ketone version of MDA could not be made quite easily, it would simply involve protection of the carbonyl with something like an acetal. Two extra steps, which of course makes it less profitable, but it can be done.

 

[slopoke]

Considering the price methylone seems to carry whenever it comes to market, i take it that is probably the main reason we are unlikely to see it anytime soon. As i've stated before i'm no organic chemist, but would those extra steps make it hugely more expensive to produce?
*makes sad face*

 

[cynosure]

Considering the price methylone seems to carry whenever it comes to market, i take it that is probably the main reason we are unlikely to see it anytime soon. As i've stated before i'm no organic chemist, but would those extra steps make it hugely more expensive to produce?
*makes sad face*

More expensive, but not hugely more expensive. Expensive enough to not make harder to make analogues since methylone sells well enough as it is. But let's face it, all of these chemicals are dirt cheap to make. They are simple molecules, and I know of places that sell/used to sell various "RCs" for $30 a gram. And I'm sure that's about how much the US business were buying them for, then selling them for $150-$200 a gram. At most, a couple of extra steps, simple protection and deprotection (maybe a loss of yield of 90% over all). but that's business i guess.

 

[sweettooth]

Here's a posible interesting naturally occuring beta-keto I have some potential to work with. If someone with some better understanding of chemical nomenclature could help me. I've been working with a chinese wild ginger species longstemmed golden earring. I since have found it not only contains asarone, and 2,4,5 trimethoxy benzaldehyde but it also has "(2,4,5 trimethoxyphenyl)-3-en-butylone" which butylone do you think its referring to sodium pentobarbitol or the pea compound? How would this differ from "beta-keto-N-methyl-alpha-ethyl-tma-2"? I know that's a lot of substitutions and chances for activity are greatly reduced but isn't that what would make it a true RC. One cool thing about this set of substitutions is that the N-methyl makes the beta-keto more stable and in theory they all kind of work together to stregnthen the "s" isomer and weaken the "r" isomer like mdma. Any thoughts or corrections on this would be greatly appreciated. Distillation points are already known so a fractioned distillation of its oil would be easy. The presence of asarone and the benzaldehyde make it seem likely it is the pea especially since the pea butylone has been around for a while before shulgin worked with it.

 

[nuke]

More expensive, but not hugely more expensive. Expensive enough to not make harder to make analogues since methylone sells well enough as it is. But let's face it, all of these chemicals are dirt cheap to make. They are simple molecules, and I know of places that sell/used to sell various "RCs" for $30 a gram. And I'm sure that's about how much the US business were buying them for, then selling them for $150-$200 a gram. At most, a couple of extra steps, simple protection and deprotection (maybe a loss of yield of 90% over all). but that's business i guess.

Well, AET used to be $60 for 100 grams back when it was available. if it wasn't for their use as psychoactives, many of them would probably be $5 a gram or less. L-tryptophan is only about $20 per 100 grams... 5-HTP about $2 a gram bulk...