Author Topic: (S)-N-ethoxycarbonylamphetamine  (Read 58 times)

highdopamine123

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(S)-N-ethoxycarbonylamphetamine
« on: September 22, 2011, 08:01:26 PM »
Its racemic version even has a CAS # 93528-35-9

I'm wondering about the pharmacology of these prodrugs.  Does anyone have any idea how fast the N-ethoxycarbonyl would get chopped off in the body? 

Found this:
Quote
Carbamate prodrugs of phenylethylamines: a neurochemical investigation
    Carbamate prodrugs of phenylethylamines: a neurochemical investigation. Baker, G. B.; Coutts, R.Several substances are used for example 93528-35-9 which is its cas registry number. T.; Nazarali, A. J.; Danielson, T. J.; Rubens, M. (Dep. Psychiatry, Univ. Alberta, Edmonton, AB T6G 2G3, Can.). Proc. West. Pharmacol. Soc., 27, 523-5 (English) 1984. CODEN: PWPSA8. ISSN: 0083-8969. DOCUMENT TYPE: Journal CA Section: 1 (Pharmacology) Following i.p. administration of the carbamate prodrugs N-ethoxycarbonylamphetamine (I) [93528-35-9] and N-ethoxycarbonyltranylcypromine (II) [91640-64-1], both at 0.1 mmole/kg to rats, the brain levels of the free drugs amphetamine [300-62-9] and tranylcypromine [155-09-9] were 9.95 and 8.95 nmole/g, resp., 1 h after the drug administration; the resp. levels of I and II in the brain were 4.15 and 4.83 nmole/g. One h after i.p. injection of 0.5 mmole N-ethoxycarbonylphenylethylamine (III) [6970-83-8] to rats, the resp. brain levels of III and phenylethylamine [64-04-0] were 15.6 nmoles/g and 190 pmoles/g; when PEA-HCl (0.5 mmole) was injected, 835 pmoles PEA/g was found in the brain. II injection inhibited brain MAO [9001-66-5]-A and -B by 79.1 and 93.4%, resp. In vitro, II at concns. equiv. to the levels of tranylcypromine found in vivo, caused 11.7% inhibition of MAO-A and no inhibition of MAO-B; tranylcypromine caused 83.9 and 99.0% inhibition, resp. Thus, it appears that the MAO inhibiting activity of II in vivo is due to the tranylcypromine formed from the prodrug. Apparently, carbamate analogs are useful prodrugs of bioactive amines.

Also I'm assuming this would work the same way if you added an N-methyl or N-ethyl (prodrug would turn into d-meth or d-ethyllamphetamine which sounded pretty good from what i've read, at least its not the evil 'meth' but nearly as good)

Like these:
http://anony.ws/di-K96L.gif

I'm wondering about the synthesis too do you necessarily have to first make d-amphetamine (or the n-methyl/ethyl) first, or is there a way to get around that leaving no traces of the "more illegal one".  Also, from what I read it doesn't seem like the ethoxycarbonyl would easily get cleaved off, compared to something like the N-hydroxy. 

Or maybe there's much better things that could be done, basically to have a "safer" stash of a favorite ADHD drug around, which appears to be a different enough drug or research chemical to any authorities.  Make it a phosphate salt too just to be different than the sulfate or HCl. 

Sorry if this a dumb topic to post, if it is let me know and maybe give me another board where I might fit in better.  I'm just trying to find various things (NOT 2-fluoroamphetamine, which i haven't tried, heard was good like amp, but has a ceiling effect i hear) that turns into the GOOD STUFF asap in your body.  But you won't technically be in posession of it (and has a different mol. weight and properties, have no idea if it would put off a marquis/other reactant test though)