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deschloroketamine as an antibacterial

vecktor

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I thought of putting this into the future dissociatives thread but I think it deserves its own thread.

MDPH which appears to be deschloroketamine has been used to treat bacterial and fungal infections,
as described in United States Patent 5811464:

http://v3.espacenet.com/textdoc?DB=EPODOC&IDX=US5811464&F=0

This invention relates to the use of 2-methylamino-2-phenylcyclohexanone and of pharmaceuticals which contain this active agent in combination with physiologically acceptable solid or liquid supporting materials or diluents for treating bacterial, fungal, virus or protozoan infections as well as for immunomodulation.
Treatment of herpetic infections

Various groups of patients suffering from lip herpes, genital herpes, herpes zoster and herpes simplex were treated by administering MPCH. The dose was 2 mg of MPCH per day for about 4-5 days. At the end of the therapy, the diseases cured more speedily to a statistically significant extent (cf. FIG. 3).

so I wonder if ketamine has similar immunomodulatory effects, it doesn't appear that the dose is high enough (2mg per day) to do anything directly against the infectous agents. perhaps this is placebo who knows but interesting all the same. or perhaps it is to do with antidepressant activity?
next time you order K then perhaps you should talk about your genital herpes :)
 

Secale_Cornutum

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Another patent about its antimicrobial properties:
http://v3.espacenet.com/origdoc?DB=EPODOC&IDX=US6083992&F=0&QPN=US6083992

And this is the ONLY patent out there that deals with its action as a dissociative anesthetic:
http://v3.espacenet.com/origdoc?DB=EPODOC&IDX=US3254124&F=0&QPN=US3254124
It says that MPCH and EPCH (the N-Ethyl version) are "particularly good cataleptoid agents". Thats it.
The patent is also of further interest since it lists more analogs that are centrally active, such as 2-methylamino-2-methylcyclohexanone (with phenyl replaced by methyl compared to MPCH) and the oxime of 1-methylaminocyclohexylphenylketone which are structurally quite far away from ketamine and MPCH.
Also, 3-methylamino-3-phenyl-2-butanone has analeptic (stimulant) activity.

I have account of MPCHs activity in vivo at doses of up to 50mg and can say the following:
- it lasts unexpectedly long! There is still a strong effect after 9 hours, and the comedown extends past 12 hours. This is a gigantic difference to ketamine.
- it is a "pure" dissociative that is not psychedelic. It feels like one would expect a clinical anesthetic to feel, separated from the world and dissociated and without emotions. There is no desire to interact with he world in any way, every disturbance from outside is annoying, even music.
It does not induce any nausea.
- it can hardly be considered to be recreational. There was no desire to repeat the experience, and it had no insight value. The long duration is also a huge turnoff, since nothing productive can be done and one is enormously intoxicated, and not in a fun way.

I think ketamine analogs are extremely interesting. What does the crazy chlorine have to do there? Why was this one chosen out of probably a hundred
other analogs to become a new valuable veterinary and human anesthetic as an alternative to the opioids and opiates with their associated dosage, respiratory depression and abuse problems?
I would really, really like to see papers of the research that Parke-Davis conducted in order to create ketamine.
I am wondering if close analogs, like 2(2-bromophenyl)2-methylaminocyclohexanone ("Bromoketamine", just Cl replaced with Br) and 2(2-chlorophenyl)2-ethylaminocyclohexanone ("Ethylketamine") have similar or equal psychotropic activities as ketamine (keeping in mind differences in potency and duration of effects, e.g. the ethyl substituent would likely increase both).

What about differently substituted analogs, like 4-chloro, or 3-chloro? Or with other substituents than halogens, like methoxy or methyl? Or ones with multiple substituents, just like Shulgin tried out new substituted phenethylamines?
There is so much to be discovered there.

Oh, and Hi to everyone here! :)

(Edit: Hmm, maybe it would have been better to post this in the other thread (dissociatives of the future). If desired, move it.)
 

Morninggloryseed

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I have always wanted to know what the bromo and iodo analogues of ketamine are like. I can't seem to ever find any data on them but I would be surprised if they have NOT been made and tested by now.
 

vecktor

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morninggloryseed said:
I have always wanted to know what the bromo and iodo analogues of ketamine are like. I can't seem to ever find any data on them but I would be surprised if they have NOT been made and tested by now.

the bromo has been made, I do not know about the iodo..

I haven't got any activity data, just the MS spectra for the bromo and derivitized version.

I would imagine that the iodo is too bulky given the size of things that work in that position, probably bromo too.

the o methyl is a known thing, and is described in the original Parke Davis patent, and in later work it is reported as a central nervious sytem depressant. I would expect it to have a shorter duration than ketamine.
 

toxide

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that's really odd that the phenyl could be replaced with a methyl and still retain dissocitaive activity. I was looking at the name for tramadol which is said to have nmda antagonist activity and it seems like if you get rid of the 3methoxyphenyl on the tramadol you'd have something almost similar to the non-phenyl methyl-ketamine analog. I could be wrong tho. This I know of to be commercially available
 

vecktor

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toxide said:
that's really odd that the phenyl could be replaced with a methyl and still retain dissocitaive activity. I was looking at the name for tramadol which is said to have nmda antagonist activity and it seems like if you get rid of the 3methoxyphenyl on the tramadol you'd have something almost similar to the non-phenyl methyl-ketamine analog. I could be wrong tho. This I know of to be commercially available

to clarify:

when we say o methyl that does not mean the phenyl is replaced with a methyl it means that the phenyl group contains a methyl group ortho (in the 2' position) to the bond which attaches to the cyclohexane ring.

structurally tramadol really is nothing like ketamine however you mess around wih the substituents on the phenyl ring. the phenyl ring in tramadol is attached in a different position to ketamine, the amine function on tramadol is attached to the cyclohexane ring with a 1 carbon spacer, and tramadol has a tertiary hydroxyl group. in fact the only thing really in common is the fact that they both contain a cyclohexane ring and a phenyl ring. so do lots of things.


if you want to speculate on the design of future drugs it helps if you look at the structures rather than just parts of the names.
 

Jamshyd

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vecktor said:
so I wonder if ketamine has similar immunomodulatory effects, it doesn't appear that the dose is high enough (2mg per day) to do anything directly against the infectous agents. perhaps this is placebo who knows but interesting all the same. or perhaps it is to do with antidepressant activity?
next time you order K then perhaps you should talk about your genital herpes :)
Actually...

Inhibition of rabies virus transcription in rat cortical neurons with the dissociative anesthetic ketamine.
Lockhart BP, Tordo N, Tsiang H.

Rabies Unit, Pasteur Institute, Paris, France.

In a previous study (B. P. Lockhart, H. Tsiang, P. E. Ceccaldi, and S. Guillemer, Antiviral Chem. Chemother. 2:9-15, 1991), we demonstrated an antiviral effect of the general anesthetic ketamine for rabies virus in neuronal cultures and in rat brain. This report describes an attempt to determine at what level ketamine acts on the rabies virus cycle in rat cortical neuron cultures. Immunofluorescence and [35S]methionine labelling of infected neurons showed that ketamine (1 to 1.5 mM) inhibited viral nucleoprotein and glycoprotein syntheses. Northern (RNA) blots of total RNA from drug-treated neurons, hybridized with 32P-labelled oligonucleotide probes for rabies virus nucleoprotein, matrix protein, and glycoprotein genes, showed a marked reduction (5- to 11-fold) in the levels of rabies virus mRNAs, relative to those in untreated neurons. No significant change in the levels of cellular beta-actin mRNA were detected in ketamine-treated cells. A similar antiviral effect was observed with MK-801; however, no inhibition of rabies virus synthesis was observed with the general anesthetic chloral hydrate. The antiviral effect was not complete; a time-dependent recovery of viral transcription and rabies virus protein synthesis was observed, but no infectious virus was released into the culture supernatant. The lack of any modification of cellular protein or mRNA synthesis by ketamine suggests an antiviral mechanism acting at the level of rabies virus genome transcription.

PMID: 1416859 [PubMed - indexed for MEDLINE]
 

vecktor

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Jamshyd said:
Actually...

very interesting.
I have noticed that since I got into K many years ago I haven't had rabies once :)
an interesting antiviral lead compound.
 

sarbanes

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vecktor said:
to clarify:

when we say o methyl that does not mean the phenyl is replaced with a methyl it means that the phenyl group contains a methyl group ortho (in the 2' position) to the bond which attaches to the cyclohexane ring.

structurally tramadol really is nothing like ketamine however you mess around wih the substituents on the phenyl ring. the phenyl ring in tramadol is attached in a different position to ketamine, the amine function on tramadol is attached to the cyclohexane ring with a 1 carbon spacer, and tramadol has a tertiary hydroxyl group. in fact the only thing really in common is the fact that they both contain a cyclohexane ring and a phenyl ring. so do lots of things.


if you want to speculate on the design of future drugs it helps if you look at the structures rather than just parts of the names.


yup. to me, tramadol looks much like stripped down codeine, down to the bare essentials. actually, electronically, it looks even more similar to methorphan. many disagree with me, but I think they are judging based on artistic criteria, and not electronic.
 

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hussness

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Secale_Cornutum said:
..."particularly good cataleptoid agents".

What would a cataleptoid agent be used for medically? Anything besides trying to model negative symptoms of schizophrenia?
 

toxide

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2-methylamino-2-methylcyclohexanone (with phenyl replaced by methyl
So is ^this an incorrect statement?
 

vecktor

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toxide said:
2-methylamino-2-methylcyclohexanone (with phenyl replaced by methyl
So is ^this an incorrect statement?

the patent doesn't doesn't say it is a dissociative.
 

sarbanes

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vecktor, so, do you think that (electronically), tramadol basically looks like very stripped down morphinan?
 

fastandbulbous

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vecktor said:
very interesting.
I have noticed that since I got into K many years ago I haven't had rabies once :)
an interesting antiviral lead compound.

How do you tell seeing that both ketamine & rabies tend to make for a person acting mad as a hatter (or even foaming at the mouth with ket - seen something a bit similar more than once!)? Maybe what you think is k-induced weirdness is actually 'la rage'? =D =D =D

PS Yes I'm back from being a grubby festival hippie... :D
 
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