Bemidone - an NMDA antagonist?

[haribo1]

Hi,
As has been thrashed out on this forum for a while, ketobemidone is illegal and likely to be VERY addictive but plain bemidone, while a poor analgesic (0.3 x meperidine in potency) is supposed to be a good NMDA antagonist. It's legal in the UK, if I read my MoDA correctly, but can anyone point to a good article discussing it's NMDA binding? Maybe a nice, cheap alternative to K?

 

[morphiquet]

i think bemidone should be designated as hydroxypethidine in the according law. and to my knowledge it's more potent than meperidine (pethidine).

 

[fastandbulbous]

Can you do a jpeg with the structure of bemidone? (I'm still a bit brain dead from a weekend of acid & ketamine)

 

[mrt50-NL]

 

[Jamshyd]

Well, that looks a bit like Ketamine (without the Cl), if I may...? I wonder how its Chlorinated analogue would behave?

 

[mad_scientist]

That picture you posted is ketobemidone.

Bemidone is known as hydroxypethidine, structure attached, and it is illegal in the UK sorry.

 

[haribo1]

OK, I mis-named it. Ketobemidone without that meta -OH grouping. That's the stuff that's supposed to be an NMDA antagonist.

 

[fastandbulbous]

Ketobemidone doesn't have an ester linkage, it's a plain bog standard ketone. Look at the picture again, there are only 2 oxygen atoms in there; hydroxypethidine has 3 oxygen atoms

Haribo1: It's OK you're not going senile, just absent minded (then again see my thinking Kara's girlfriend was pekkie in EADD - it comes to us all with age!)

link to ketobemidone structure

 

[morphiquet]

so you mean desoxy-ketobemidone

 

[fastandbulbous]

^ Possibly, but desoxy usually applies to aliphatic alcohols as far as I know and as it contains 2 oxygen atoms, that's a bit vague

1-(4-phenyl-4-piperidyl)propan-1-one there we go, announcing ambiguity abolished (acceptable alliteration all? )

 

[haribo1]

So, Bemidone... or whatever it's called...

OK, well, ketobemidone without the meta-OH. The old (1950s) called it bemidone for some reason, thats my excuse The fact remains that it's supposed to be a good NMDA antagonist but poor opiate. It would be a LOT simpler to make (N-methyl piperidone + cyanide + phenyl lithium followed by grignard). <-That's not too specific is it?

SMILES CCC(=O)C1(CCN(C)CC1)c1ccccc1
CAS 7475-63-0