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Flephedrone

p-methyl group on an otherwise unsubstituted phenyl ring gets metabolised fairly quickly to COOH which is too polar to cross the blood brain barrier, and so you would expect both p-methylmethcathinone and p-methyl(meth)amphetamine to be shorter lasting than the parent compounds.

Not sure how it works when there are other substitutions on the ring, 2CD is particularly short acting also, but then DOM seems to last just as long as the other DOx drugs so maybe the rapid metabolism only happens when the p-methyl is the only group on the ring. Also not sure if this also applies to meta-methyl groups as well, I'm pretty sure it doesn't hold true with the ortho- substitution.
 
I couldn't find any information as I don't have the backup of the Hive archive on my current computer. But I'm pretty sure there are some information on it in there, as well as some russian forum (probably but not entirely sure it was hyperlab). I guess time will tell, and in this case quite soon.
 
mad_scientist said:
p-methyl group on an otherwise unsubstituted phenyl ring gets metabolised fairly quickly to COOH which is too polar to cross the blood brain barrier, and so you would expect both p-methylmethcathinone and p-methyl(meth)amphetamine to be shorter lasting than the parent compounds.
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Have you got a reference for that because I thought that the ring methyl group was pretty much bullet-proof (eg toluene isn't metabolized to benzoic acid by the body)? When there's a nice polar group for enzymes to work on (either the amine or the keto oxygen in this case), that's generally the primary site of metabolism; even then with the likes of amphetamine etc, the majority is either deaminated or excreted unchanged and only a small percentage is para-hydroxylated. Put a methyl group in the 4-position and that'll bugger ant para-hydroxylation from happening.

If it's short acting, my money is on increased renal clearance or deamination with nothing happing to the ring methyl group
 
Well its said that simple Toluene is metabolised to Benzoic acid,the reason it is not toxic (contrary to benzene).Altough I have no reference to that and how this plays out in the substituted phens is Another question.
 
Maybe I'm thinking about something else and getting facts jumbled (& incorrect :)), but pyrovalerone, which has a 4-methyl group on the phenyl ring doesn't get metabolized to a benzoic acid derivative & considering the similarity between mephedrone & pyrovalerone I'd think it highly unlikely that mephedrone is metabolized to a compound with a 4-COOH substituent
 
I'm sure it says in my toxicology notes somewhere that ring methyl groups can get metabolised to COOH, but said notes are in storage in another country so I can't check right now...

DOM certainly gets metabolised to DOCOOH but no idea what percentage of it is converted, maybe it is an available route of metabolism but only a tiny amount actually goes down that pathway?
 
I was under the impression that the nontoxicity of toluene relative to benzene, specifically its carcinogenic effect, was due to the methyl group negating the flat, planar configuration of benzene and making it too bulky to intercalate DNA.

?
 
Nope, the lower toxicity of toluene in comparison to benzene comes from the high selectivity of the metabolizing enzyme for the methyl group, forming mainly (ca. 95 % ) benzyl alcohol. The few remaining percent that are metabolized benzene-style towards the epoxide can be scavenged easily by glutathione or by sponateous rearrangement to phenol.

Toluene is metabolized and then excreted as benzyl alcohol and benzoic acid.

BUT: Toluene isn't exactly p-methyl amphetamine or alike. So plz be cautious with applying known metabolic pathways.
 
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fastandbulbous said:
* shuffles off quietyly hoping nobody notices * =D
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^
^
*does notices but silently shuts up*

So, back onto the topic... This means the presence of para fluoro group shuts of the (possible) carboxylation metabolic pathway and goes for beta-hydroxy and/or deamination?
 
Yep, exactly...I think, these are the 3 main metabolic pathways that the compound can go, not much else possibilities IMO.
 
It seems that someone has decided to make the para-chloro cousin to this. Any thoughts about its likely toxicity?
 
djfriendly said:
It seems that someone has decided to make the para-chloro cousin to this. Any thoughts about its likely toxicity?
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Probably highly neurotoxic seeing as para-chloroamphetamine is used in research for selectively destroying serotonergic neurons in the same way that 6-OH-dopamine is used for destroying dopaminergic neurons...

On the other hand the cathinone derivatives do seem to be less neurotoxic than their amphetamine cousins, but still no way would I touch p-chloro-methcathinone or advise anyone else to either.

The p-fluoro is the only halogen that seems to lack neurotoxic potential, Cl, Br and I are all pretty nasty in this respect - although oddly enough this does not seem to be the case when there are 2,5-dimethoxy groups on the ring.
 
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