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Stimulants of the Future

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Dreaming...

Ok I'm the first to admit I am not the best at this but just thinking aloud I was looking at the structure and comparing it to desoxypipradol...

What do you think of these compounds...

Compound A is similar to 2-aminoindan and the second has an indole. Good possibility / Bad possibility?

I definately like the look of compound A (if its chemically possible)
 

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Oh and also just made the link 2-phenylcyclopentylamine is very similar to tranylcypromine Parnate® (the maoi antidepressant currently available on RX)
 
I have just read up on some basic aromatic amines, aniline etc and the word poison came up, I think I understand.
 
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The lipophilicity, combined with having a basically unmetabolizable group (good luck at puckering that ring correctly Mr. MAO) at the major metabolic site would make it seem that the cyclopentyl compound would last for days and days. Maybe for long range fighter pilots?
 
Drugs don't need to be metabolized to be got rid of (esp if it already has a polar group to facilitare the kidney's job of removing it) so it;ll just get pissed out unchanged. If you think of muscimol, it;s excreted unchanged but doesn't last for days.

Besides, from what I've read about it, it's about the same half life as amphetamine
 
I know about unmetabolized excretion and I know the pH dependence of the excretion for the amphetamines, it just appeared that being so fatty, this bugger would want to spend a lot of time out of the blood stream.
but if the half-life~~amphetamine, interesting.
 
It's been considered as an antidepressant/psychostimulant in the past, but I don't know why it didn't make it to clinical trials. As regards the half life being about that of amphetamine, that's in several species including primates, but I can't find anything in my notes about it that refer to half life in man. Mind you, if you're getting those sort of figures for a whole range of species, including rhesus monkeys, I can't imagine that in man it;'ll be radically different. (Sorry but refs in my notes only refer to Journal of Pharmacology & Experimental Theraputics - JPET. I didn't note down the journal no or page - I know that's my main fault, that I'm a sloppy records keeper).

As regards it's lipophillic tendancies, 2-phenylcyclopentylamine isn't going to be that different from fencamfamine w.r.t. the non-polar part of th molecule (I realize fencamfamine is a secondary amine, but it's metabolite with the N-ethyl group removed is active but doesn't hang around in the body significantly longer than its parent compound). My only area of 'what if' left surrounding it is it's ability to act as a competitive inhibitor of MAO 2-phenylcyclopropylamine )tranylcypromine/Parnate) is about the most troublesome clinical MAOI whereas fencamfamine is a competetive inhibitor that is weaker than amphetamine. Where the 5 membered ring lies on this scale is the last barrier to it being a potential 'new wonder stimulant'. Will report back when I find out one way or the other
 
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^ I love these threads, you learn so many new compounds.

Nomifensine does look similar, I was unaware so many Dopamine reuptake inhibitors have been available for medical use in the past.

Until recently I was one who viewed the history of antidepressant / stimulants as being something like Tricyclics -> SSRI -> SSRI/SNRI etc & latest atypical. With Methamphetamine / amphetamine / phenmetrazine floating around in the background.

I might see if I can find any other similar compounds in the literature, Pleased my compound has passed phase one of bluelight hypothesizing =D
 
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http://www.google.com/patents?vid=U...ct&zoom=4&dq=stimulant+novel+compound#PPP2,M1

Abstract
A series of novel 4-phenyl-1,2,3,4-tetrahydro-1-naphthylamines, including their pharmaceutically acceptable acid addition salts and their cis- and trans-isomers, have been prepared. The trans-isomers are useful in the field of mental health as antidepressant agents and/or as psychomotor stimulants. The trans-isomer of N-methyl-4-phenyl-1,2,3,4-tetrahydro-1-naphthylamine represents a preferred embodiment.
 

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Reminisant B said:
Anyone heard of Sydnocarb?

http://jpet.aspetjournals.org/cgi/content/full/288/3/1298

Looks like an incredibly complicated pro-drug of amphetamine.
Click to expand...

No it looks well dodgy as its not a derivative of alphamethylphenethylamine, but a dreivative of alpha-methylphenethylhydrazine (has a N-N bond) and alpha-methylphenethylhydrazine is a fuck-off non-competitive inhibitor of MAO. If iy is a pro-drug, it will form the hydrazine not the amine compound (and that isn;t at all good or healty)


chemical structure of syndocarb
 
fastandbulbous said:
No it looks well dodgy as its not a derivative of alphamethylphenethylamine, but a dreivative of alpha-methylphenethylhydrazine (has a N-N bond) and alpha-methylphenethylhydrazine is a fuck-off non-competitive inhibitor of MAO. If iy is a pro-drug, it will form the hydrazine not the amine compound (and that isn;t at all good or healty)


chemical structure of syndocarb
Click to expand...

sidnocarb has been very very widely used in the former soviet union, it is considerably less toxic then amphetamine, though is a less powerful stimulant. it has not,I believe, significant MAOI activity.
it is a member of the syndone or sydnone (the two names are interchanged though sydnone is the iupac approved name)class of drugs about which I know very little as the literature is almost entirely in Russian.
 
^^ Just the first thing I saw was the N-N bond and all of the phenethylhydrazines are non-competetive MAOI. I suppose if the ring isn't opened up it doesn't need to act as a MAOI. I'd need to see clinical data in English (or some language I can bribe my wife to translate from, such as Hebrew) before I'd consider eating any
 
Sidnocarb/sindocarb/sydnocarb - I thought I had heard it somewhere before, its talked about in the carphedon thread.

Possibly might not be controlled in some countries then.....? Although by the sounds of things its not very good.

Interesting about the chemical structure.
 
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^ I think* that means it can form the cation or anion form. I.e

Sindocarb Hydrochloride

or

Sindocarb Sodium
 
I've been looking on Spanish language sites for prolintane (Reactivan) but they all seem to indicate it's off the market.

This is your free 1st almost warning. Do not ask for sources again or it's warning time
 
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hussness said:
What's the +- on the ring with the N-N-O structure on sidnocarb?
Click to expand...

it means that the structure cannot be accurately represented with a simple drawing, the ring contains unbalanced charges which move around, the plus minus is just a way of trying to show this, there are quite a few nitrogen compounds which cannot be accurately represented on paper.

sidnocarb = Mesocarb

http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=7312716&dopt=Abstract
 
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