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Tranylcypromine/Phentermine hybrid idea.

Smyth

Smyth

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Any idea if "Tranyltermine" is a good compound to make?

Tranyltermine.gif


I'm thinking that carbene chemistry may be involved on the nitrostyrene but I dont know how the nitro group will reduce and leave the cyclopropane unit unchanged.

I also wonder if amphetamine-like activity is possible with bicifadine
if the plain phenyl analog is prepared/consumed?
 
The idea is not so novel as you might think...


Kaiser, Carl; Lester, Bruce M.; Zirkle, Charles L.; Burger, Alfred; Davis, Charles S.; Delia, Thomas J.; Zirngibl, Ludwig
"2-Substituted cyclopropylamines. I. Derivatives and analogs of 2-phenylcyclopropylamine."
Journal of Medicinal & Pharmaceutical Chemistry 1962, 5, p.1243
DOI: 10.1021/jm01241a017
Abstract
A series of derivs. (I, II) of 2-phenylcyclopropylamine and analogs, 2-arylcyclopropanecarboxhydrazides, -carboxamides, -methyl-amines, -carboxylic acids, esters, and chlorides has been prepd. in order to study relationships between chem. structure and monoamine oxidase-inhibiting activity.
Click to expand...


Zirkle, Charles L.; Kaiser, Carl; Tedeschi, David H.; Tedeschi, Ralph E.; Burger, Alfred
"2-Substituted cyclopropylamines. II. Effect of structure upon monoamine oxidase-inhibitory activity as measured in vivo by potentiation of tryptamine convulsions."
Journal of Medicinal & Pharmaceutical Chemistry 1962, 5, pp.1265-84
DOI: 10.1021/jm01241a018
Abstract
The monoamine oxidase (MAO)-inhibitory activity of numerous analogs and ring-homologs of 2-phenylcyclopropylamine, and related compds., as measured in vivo by potentiation of tryptamine convulsions, has been detd. The results indicated that the structural requiremerits for potent in vivo MAO-inhibitory activity in this class of compds. are: (1) a cyclopropane ring, (2) an amino group attached directly to the cyclopropane ring, and (3) a 2-substituent containing an aromatic moiety. On the basis of an examn. of mol. models of cyclopropylamine derivs. and other types of MAO-inhibitors, possible modes of interaction of these compds. with MAO have been considered.
Click to expand...


This should be a good start to gather more information.

Ahoy, Murphy
 
...and furthermore does 1-benzylcyclopropane act as both competitive and irreversible (=covalent!) MAO-inhibitor. See J Med Chem 1985, 28, p.1953.


- Murphy
 
Good find. Do you think you can possibly upload them so that I can read?

Start a thread up in the stimulant section or something.

Tranylcypromine is good compound for people who havent tried it yet.

I am very appreciative of your helpfulness in retrieving potentially valuable nuggets of information.
 
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Another idea is to replace the methine in tranylcypromine with a sulfur atom.

This is just ramble of course.

The dichlorocarbene idea seems worthy of some thought.
 
a bioassay of the benzylcyclopropane compound has been posted on this site by dr Heckyll, the stuff appears rather spectacularly bad.
 
Update from the dark side:

I've missed to mention a bioassay that didn't sound very inviting. In short:
200-300 mg taken orally. First collapse after ca. 20-40 min (estimated from the report). Waking up in the ER and getting told by the physician about heavy heart arrhythmia. Despite better knowledge trying to leave the hospital. Second collapse just some minutes later...


Well, the dosage may have been 'a bit' high, but it shows where we're heading to with this compound. Any volunteers for further trials? :\

- Murphy
 
One could try a naphthyl instead of a benzyl group. That would keep matters innovative.
 
Sorry, moronic acid is already known, some big, ugly-arse terpene , bearing no MDO-ring.

Although 'moronate' as a salt derivative has a nice ring to it, as in 'which moronate that...its probably toxic'
 
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