benzedrone 4-mbc, 4-mmc prodrug?

[klfiend]

http://en.wikipedia.org/wiki/Benzedrone

Anyone hazard to guess if this would be a 4-mmc prodrug? Behaving similarly to benzphetamine?

http://en.wikipedia.org/wiki/Benzphetamine

Someone who knows more than me tell me where the liver would cleave this molecule, would it make it into 4-mmc and a free phenyl group (that bonds with?) or maybe it would make 4-methylcathinone and cleave of the methylphenyl (to bind with?)

Any info appreciated, not much out there on this compound...

or could it be active on its own?

 

[ebola?]

Honestly, it just might be. Someone more knowledgeable than me should chime in though. I'd be worried about metabolism of the beta-ketone to hydroxyl, though, leading this to be more of controlled release 4-methyl-ephedrine than controlled release 4-methyl-methcathinone (the former is cardiotoxic shit). If this does 'work', in vivo, though, it'd be a godsend: mephedrone is woefully brief in duration, and its brevity contributes heavily to its addictive profile.

ebola

 

[Alcyone]

It wouldn't be a prodrug of mephedrone/4-MMC, as it's lacking an N-methyl. It would metabolise into 4-methylcathinone and benzoic acid.

While benzphetamine is a decent prodrug of methamphetamine, it's only about 20% the potency of methamphetamine (rough estimate based on personal experience, one 50 mg Didrex equals about 10 mg meth). If those numbers are anything to go by, you'd need and awful lot of 'benzedrone' or its N-methyl analogue to approximate a typical mephedrone dose.

As ebola? pointed out, there's a chance that the beta-ketone is reduced more rapidly than the N-benzyl is cleaved off, which would be a very bad thing indeed. The cathinones with bulky N substituents, esp. the pyrovalerones, seem to be more stable towards ketone reduction than the N-methyl ones, so I guess this one might stand a chance.

 

[FlippingTop]

This is a quote from another forum refering to 4-MBC:

The benzyl group of 4-methyl-N-benzilcatinone can be easily removed [snip] to produce the 4-methyl-cathinone. This product for subsequent reaction of nitrogen methylation, produces mefedrone.

(translated)

 

[(zonk)]

I believe I received some benzedrone by accident as the supplier kept seeming to be getting it confused with brephedrone(what I ordered)... I know that's not good but I guess at least he wasn't mixing it up with any 'ol chem.
Anyway I mainlined enough over an hour to probably kill a man and nothing at all! So I figured if this was 4-MBC as I speculated it should be active orally so I downed a horse pill sized gel cap almost full(but not packed in)as my tolerance to serotogenic stims is pretty high and these types of prodrugs also require much greater doses. Orally it worked and I mixed in some 6-APB into the "roll"(a bit later) to make it a more proper roll. I would say that this drug is not very potent at all.
I was thinking about soaking the remaining 4-MBC in HCl to get 4-MC(if that's the right way to do so?)but then how unstable is the 4-MC?

 

[Wark]

It wouldn't be a prodrug of mephedrone/4-MMC, as it's lacking an N-methyl. It would metabolise into 4-methylcathinone and benzoic acid.

What makes you think benzoic acid would be formed? That would require hydroxylation at a very unreactive carbon, unless I'm wrong. However, I agree that 4-MMC would at no point be formed.

 

[Alcyone]

^ Unreactive carbon? Even something as comparatively inert as toluene is metabolised mainly by oxidation of the methyl group.

I'm afraid I can't offer you a reference off-hand, but to the best of my knowledge, the N-benzyl derivatives of phenethylamines are metabolized by oxidative cleavage of the benzylamine bond, yielding the N-desbenzyl phenethylamine and benzoic acid (by way of benzyl alcohol and benzaldehyde).

Of course I could be wrong. If we accept the fact that benzphetamine is a prodrug of methamphetamine, what's the likely metabolic fate of the benzyl group which is lost? I strongly doubt it would be eliminated as toluene. Most metabolic N-dealkylations catalysed by the various CYP isoenzymes typically result in the dealkylated amine and the alcohol corresponding to the alkyl leaving group.

 

[ebola?]

Anyway I mainlined enough over an hour to probably kill a man and nothing at all! So I figured if this was 4-MBC as I speculated it should be active orally so I downed a horse pill sized gel cap almost full(but not packed in)as my tolerance to serotogenic stims is pretty high and these types of prodrugs also require much greater doses. Orally it worked

What would you estimate the total dosage ingested to be? What is your 'usual' dose of serotonin releasers? What was the subjective feel like before you added the 6apb?

It looks like 50 mg is a typical (if slightly high) beginning dosage for benzphetamine. Given that 5 and 10 mg / dex are typical starting doses, We should expect 1/5th or so the potency for benzedrone in comparison to mephedrone (we should EXPECT! please, no one go eating over half a gram of a nearly completely novel compound.)

ebola

 

[(zonk)]

1g in total
Since ROA was IV 100mg should have had me floored but even after many IVs nothing was felt. I assume the capsule had 300-400mg in it which is around my area for most entactogens as they generally have the same dosage give or take

Although I wasn't rolling super hard or anything, a +2 I guess

 

[crOOk]

I'm afraid I can't offer you a reference off-hand, but to the best of my knowledge, the N-benzyl derivatives of phenethylamines are metabolized by oxidative cleavage of the benzylamine bond, yielding the N-desbenzyl phenethylamine and benzoic acid (by way of benzyl alcohol and benzaldehyde).

Lol you said cleavage.

 

[Alcyone]

Lol you said cleavage.

Yeah, so what? Did I turn you on?

I bet you'd really love an alkaline ester hydrolysis. First I get the ester nicely lathered up with plenty of soap. I'm really careful to get both halves properly covered so I don't miss a spot. Then I get the shower running and use a stream of nice warm water to squeeze in between there and pull the alcohol and the acid apart. That's hydrolytic cleavage for you. Organic chemistry is totally hot, you know.

 

[crOOk]

ty for the midnight lulz! :D

and there i was thinking alkaline hydrolysis was something only morticians get off on.

 

[ebola?]

BLUELIGHT NIGHTS, y'all.

 

[kah8]

I've a sample on way, really don't know the dosage I'll use.

 

[ebola?]

Since ROA was IV 100mg should have had me floored but even after many IVs nothing was felt.

Since this is a suspected pro-drug with high oral bioavailability, IV'ing shouldn't have increased the potency a great deal. Additionally, mephedrone itself has a pretty brief duration of action, so maybe serum levels of mephedrone never climbed that high. Over how long did you take this gram?

ebola

 

[Alcyone]

IVing a prodrug which relies on first pass metabolism to be converted into its active principle isn't a great idea in the first place. Secondly, it won't be converted into mephedrone, but 4-methylcathinone (mephedrone without the N-methyl). Who knows what 4-methylcathinone is good for? My guess is that it would retain most of mephedrone's DA and 5-HT releasing activity, but the lower lipophilicity would indicate that it's less able to cross the BBB and therefore less potent than mephedrone.

In short, benzedrone appears to be a poor prodrug for a weaker version of a shitty compound.

 

[phatass]

Yeah, so what? Did I turn you on?

I bet you'd really love an alkaline ester hydrolysis. First I get the ester nicely lathered up with plenty of soap. I'm really careful to get both halves properly covered so I don't miss a spot. Then I get the shower running and use a stream of nice warm water to squeeze in between there and pull the alcohol and the acid apart. That's hydrolytic cleavage for you. Organic chemistry is totally hot, you know.

orgasmic chemistry

 

[puzzlehead]

a shame for life or a promising start?

orgasmic chemistry

lol, nice phrase i will use this as kind of my motto, makes my career sound like the rockstar-life it is :-D

thank you very much that a thread for a likely vanished (rather fast i guess) substance ends with something so megalomanic to write on my banner...

you see, it was me who "invented" this particular obscure cathinone. but then my office burned down (rcs valencia, i hope i am allowed to write something which is ptetty well known and i own a legalized business now (no, the name and address have changed so the above ain't source discussion, rather nostalgic rambling...



so, the benzcathinone: it was my first design i came up with completely on my own. even less education in the field than now (we live and we learn, or so it is said), no literature search, no xiscussions. just stumbled across benzphetamine, was impressed (by now i am more impressed that we aren't flooded with MMA and 4-MMA (second one hopefully was abandoned when 4-MA got scheduled for its horrid neurotoxity...)

so, what i would like to ask the real educated crowd about their opinion about some engineer imagining that benzphetamine would somehow work identically or extremely similar with cathinones, finding a lab to get it on the market (that idea is horrible reckless, lets not talk about that) and then the finished product gets stolen from our spanish "soon to be partners" together with 1/3 my company and they release it. completely clueless themselves they trust a computer scientist.

but all in all... it worked (honestly i was hoping for 4-MMC and cathine to be biosynthed) and it had at least no hazmat-style metabolic byproduct. and and hey: try finding my "post-drug-cathinone anywhere in nature or synthing it. (for whatever reasons you come up with) good luck (isnt it extremely unstable like a primary amine or so...



anyhow, excuse the rambling, i am on a alpja-PBP binge since the day the mail came.

what i want to hear from some of you with post-grad or currently in the studium is this: do we take brepjedrone as a shame for life or a promising start into drugdesign, because it is a hint towards serendipity and a certain chem intuition, considering my lack of proper educathion and no help at hand...

shun me now or wait for whatever i come up with

message typed on my (shitty) nokia 520 which doesn't even have swipe

 

[sekio]

bumping threads from 2 years ago just to revive/discuss the idea of another shitty cathinone is not really what we go for here on bluelight

thanks

closed

 

[ebola?]

A couple points of clarification:

1. yeah, one may only name vendors that are out of business (and not returning) here.
2. adding a benzphetamine-like mechanism to entactogens seems to work quite poorly, due to the parent-compounds' comparatively low potency, entailing that really high doses need to be taken (as the effects are spread over a longer period).

ebola