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I Like to Draw Pictures of Random Molecules

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108ehkw.png


Hi all, recently I was reading up on melatonin receptor agonists and noticed that a common MT1&2 agonist, agomelatine, is essentially melatonin with a naphtyl ring instead of indole.

Now the obvious question occured to me, if anything is known about the activity of the naphtyl analogs of the common psychedelic simple tryptamines?
 
hjalmar said:
108ehkw.png


Hi all, recently I was reading up on melatonin receptor agonists and noticed that a common MT1&2 agonist, agomelatine, is essentially melatonin with a naphtyl ring instead of indole.

Now the obvious question occured to me, if anything is known about the activity of the naphtyl analogs of the common psychedelic simple tryptamines?
Click to expand...

Agomelatine has the alkylamino chain one higher - although both variations might be active.

1zft1dh.png


Agometatine is a 5ht2c antagonist so could be logical to epect similar effects in related compound maybe.
 
^ That would be my guess as well. It's essentially just a ring-opened homologue of desoxypipradrol and 2-(diphenylmethyl)pyrrolidine, which have been shown to act as NDRIs (and highly potent ones at that).
 
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Well now that this thread is getting serious, here's something silly.
:P
A constrained (?) methamphetamine analogue. Or 2,5-dimethoxymethamphetamine. I went all out with this lil diagram lol
nRP8W.png
 
ktp said:
ritalin-meph-hybrids:

2dlkccj.png
Click to expand...

Not necessarily the 4-methyl BUT would be interested to see if the structurally simplified version of methylphenidate (like the bottom chemical) would still hold true as a dopamine reuptake inhibitor(maybe by even using alpha-ethyl). Reminiscent of tramadol to tapentadol simplification.
 
Dreamt up this molecule, can anyone tell me if it sounds promising? 5-methyl-MDE

or 5-methyl-3,4-Methylenedioxy-N-ethylamphetamine

Basically the same reasoning behind 5-methyl-MDA with n-ethylamphetamine rather than n-methylamphetamine. Are there any obvious flaws in my reasoning? 5-me-MDA was around 5x more potent than MDA if IIRC read that on wikipedia.. Wondering if it would fall victim to steric hindrance?
 
Not necessarily 'fun' compound but would be intersted to see what a 4-methylmethcathinone - bupropion hybrid would result in (more for curiosity) - aside from possible lowering of seizure threshold

n48e4p.png


Might increase monoamine releasing properties
 
347fmfl.png


How about these guys? Apparently electronegative beta substituents are well tolerated. They've been synthesized (a quick google of beta-fluoroamphetamine will tell you that) but not tested as far as I can tell.
 
could the metabolites potentially be more dangerous than other flourinated amphetamine analogues, due to the flourines being attached to the alkyl group?
 
Found a study on the difluoro variant in rats. Acted as a stimulant, half-life a little over a third that of amphetamine, higher dosage.
http://www.sciencedirect.com/science/article/pii/0006295272902912

Edit: Found a citation for "Tissue distribution and metabolism of amphetamine, β-fluoro-amphetamine and β, β-difluoro-amphetamine in the rat" by RW Fuller et al. in the Pharmacologist, 1971. The article is nowhere to be found on the web.

What about alpha fluoro? Probably wouldn't ionize at all at physiological pH, would it? :\
 
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er, don't know. Fluoroalkenes are very dangerous, fluoroalkanes and aryl are not very dangerous... Benzyl fluorides might be somewhere in between due to resonance of the ring? It's probably ring substituent dependent, too.
 
nuke said:
er, don't know. Fluoroalkenes are very dangerous, fluoroalkanes and aryl are not very dangerous... Benzyl fluorides might be somewhere in between due to resonance of the ring? It's probably ring substituent dependent, too.
Click to expand...

Mmm I don't see why a benzyl fluoride would be more dangerous than a fluoroalkane or a fluorobenzene.
Just speculation though, hard to predict this stuff :P

Gah, if only I still had access to webMO.
 
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