Prodrugs for d-amphetamine. N-OH? N-?

[pete_gasparino]

Also are both d-amph and d-methamp both the (R) versions? If I add anything to the nitrogen it switches to an (S).

The dextro enantiomers of these compounds have (S) configurations. So thats probably why when you add a substituent (if you are using ChemDraw or something like it), the configuration changes to S, as it should.

So would (S)-N-(1-phenylpropan-2-yl)hydroxylamine = N-hydroxy-dextroamphetamine? (the good stuff).

The 'dex' prefix stands for 'dextro', which refers to the optical properties of the molecule. There's no way to determine whether a given R or S molecule is (+) or (-) but by measuring the optical rotation.

Some websites say that d-methamp = (S)-N-methyl-1-phenylpropan-2-amine (while others say its still (R) ). Where as the unsubstituted nitrogen (dextroamphetamine) is (R)-1-phenylpropan-2-amine.

The (S) configurations of both molecules are dextrorotatory.

I guess in this case, its just easier to say dextro or levo if the R/S thing complicates things a bit. Dextro is the good stuff, Levo is mostly PNS (generally speaking although i've had decent racemic amp before)

The dextro, levo, (+), (-), d, l prefixes refer to the direction in which a molecule rotates plane-polarised light. The R/S configurations depend only on the configuration of the substituents around the chiral centre. Use the Cahn-Ingold priority rules to assign stereochemistry to a chiral centre.

If you are doing organic synthesis or considering synthetic methods, this is rather important to understand, as enantiomers can have quite different biological activity and effects.

 

[Cortexiphan]

Concerning hydrazines, Carbidopa is commonly used in conjunction with levodopa for treament of Parkinsons. However i do not know if a phenethyl-hydrazine analogue would be metabolized to the phenethylamine.