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ketamine analogues info

anhalonium9

anhalonium9

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does anyone have an positive extented research notes on ketamine analugues. i know of two from brief metions, but i would like more information on pychodyaminics and the likes. human trials. whatever. as i understand they are longer lasting than ketamine. i am intriged. more please. arylcyclohexalamine are fascinating. and no i'm not interested in tiletamine.
 
Shown below is 2-phenyl-2-N-ethylaminocyclohexanone (ket has an ortho chlorine atom attached to the phenyl group and is N-methyl as opposed to N-ethyl) is about 3-4 times the potency of ketamine, but has a similar half life etc. Basically you can do with ketamine exactly what has been done with PCP in regards of the amino group ie. replace the methylamino with ethylamino, dimethylamino, piperidino, pyrrolodino etc and still have active compounds. Replacing the 2-chlorophenyl with an aromatic heterocycle produces compounds like tiletamine that are much less acceptable in terms of psychedelic use


59655ketamine_analogue.JPG
 
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i wonder what the pharmacology of the cyclized (a spiro-isoquinoline of some sort that i'm to tired to try to name right now) analog of that ethylamino compound would be.
 
Another variation on the aryl-C-N structure (effectively benzylamine derivatives) is lefetamine (shown below)

lefetamine.JPG


Lefetamine also has a fair amount of mu receptor agonist activity as well. Not bad for such a simple structure
 
^
Does that mean it would constrict your pupils? or just opiate-like euphoria? or more like dxm with big pupils?
 
ok but could you explain what the syptoms or effects of mu-agonism are? Would it make it an opiod is what i mean (I think) or more a dxm like experience , I know it's someway related to opiates but only cause i read it somewhere , nothing in common with opiates when used recreationally.
 
F&b, your structure of lefetamine (SPA) isn't quite right, it's the dimethylamine. SPA is a µ-opioid and abusable, but potency is low and doses in case of abuse quickly go into the gram-range.
 
^ Ah, right - that's what you get from trying to do something from memory! - I will modify & update it. Cheers

and doses in case of abuse quickly go into the gram-range.
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That seems quite strange considering that it's also an NMDA antagonist (re; their ability to reverse tolerance for mu agonists)
 
Pharmacol Res Commun. 1984 Sep;16(9):915-22.

Clinical and experimental evidence of an opiate-like activity of lefetamine.

Paroli E, Nencini P, Moscucci M.

A case of lefetamine abuse (0.9-1.8 g/day in 15-30 i.m. divided doses) is reported. In this patient, the administration of naloxone precipitated a mild opiate-like withdrawal syndrome, characterized by mydriasis, piloerection, yawning and a slight increase of blood pressure. The complete withdrawal of lefetamine, substituted by a placebo regimen, aggravated these symptoms. Furthermore, experimental results showed that lefetamine induced a naloxone-reversible inhibition of the guinea-pig ileum contractile response to electric field stimulation, and that naloxone pretreatment of mice prevented lefetamine antinociceptive activity in the hot-plate test. The clinical and experimental findings suggest that lefetamine has an opiate-like activity.

Publication Types:
Case Reports

PMID: 6095332
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Corrected lefetamine structure

Here's the updated (read: correct) structure of lefetamine; also included is the structure of PCP for comparison and an intermediate hybrid of the two (with possibly more NMDA antagonist activity)

relation_to_PCP.JPG
 
first time i've ever heard of lefetamine. you guys are great. i wish i could pick thru your brains with a fine tooth comb. anyway, has this ever been seen outside the lab, i.e. abused. where could one find out more info on lefetamine. any other members of the ketamine family that stand out beyond just possibilties. i remember reading somewhere that there are k analougues with longer duration.

opiate activity in a pyschedelic dissociative sounds very interesting (yummy) and abusable to say the lest. there must be other suprises in such a "special" family. if only one could dream these dreams.

btw,f&b, those last two images didn't seem to show up on my browser.

also....SPA? huh. please explain as i might be a little slow on the technical side of arylcyclohexalamine.
 
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trade name meaning it's been/being marketed? for what indications, if so? do you know how i can find out more. i'll search engine it, but any and all info would make my day.

the structure between lefetamine and pcp....thats a pcp analogue, am i right. has it been synthesized and does it display any opatie agonist activity?

btw....f&b, sorry if im asking too many ?s, but your my fucking hero man. i wish i had half the brain you have.
 
what about 1-(1,2-diphenylvinyl)piperidine, it would have the quaternary carbon that is present in pcp and ketamine (as well as tiletamine, memantine and whatever other arylcyclohexylamines you can think of).
 
oh right, sorry, that's what my mother would call a "brain-fart". that's what i get for habitually staying up until 5am, oh well...

so now that i'm more awake, what about
9-(9,10-dihydrophenanthrenyl)piperidine?
 
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Lefetamine (SPA) combining amphetamine with opioid-like effects, a drug of wide abuse in Japan in the fifties, has now been introduced as such in Italy. In this study the drug was tested to verify its resemblance to opiates. Ten lefetamine abusers were hospitalized and then subjected to naloxone- and pentazocine-tests and detoxified. Moreover, lefetamine was administered to ten opiate addicts with an acute withdrawal syndrome and to ten methadone-treated addicts. The naloxone-test was positive and pentazocine could be substituted for lefetamine. Lefetamine was able to relieve opiate withdrawal and did not precipitate withdrawal symptoms in stabilized opiate addicts. It is concluded that lefetamine may act as an opioid partial agonist.

source=Entrez Pubmed
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crOOk
 
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