1-Phenyl-2-propanol: an amphetamine replacement?

[annonymous]

I was inspired by reading: "Improving immunogenicity and overcoming self-tolerance: by replacing strategically chosen tyrosines with p-nitro phenylalanine, a tolerated self-protein can be made immunogenic." (http://en.wikipedia.org/wiki/Expanded_genetic_code) I noticed that replacing tyrosine with p-nitro phenylalanine would just be replacing a hydroxyl (OH) group with an amino group (NH2).

similarly, the only difference between GABA (the primary inhibitory neurotransmitter) and GHB is that GHB has a gamma hydroxyl group instead of a gamma amino group.
GABA = gamma amino butyric acid, GHB = gamma hydroxy butyric acid (might as well be GHBA)
so what i am wondering involves the line "Improving immunogenicity and overcoming self-tolerance."

this is amphetamine: http://upload.wikimedia.org/wikiped...tal.svg/220px-Amphetamine-2D-skeletal.svg.png

this is 1-phenyl-2-propanol: http://www.chemexper.com/cheminfo/s...t=false&maxWidth=250&maxHeight=170&format=png

Almost the same compound, except for an amino (NH2) is exchanged for a hydroxyl (OH) group. These two are next to each other on the periodic table and exhibit similar electronegativities.
I wonder if 1-phenyl-2-propanol would act similar to amphetamine, but without any preexisting amphetamine tolerance?
Is there any documented use of this 1-phenyl-2-propanol compound?
thanks

 

[flaming]

Phenyl-2-propanol is a common impurity in methamphetamine, as methamphetamine synthesis often starts with phenyl-2-propanone, which is readily hydrogenated to form phenyl-2-propanol. I don't believe it's active but I have no source to confirm that. Most literature I have seen on it documents it only as a byproduct/impurity in methamphetamine manufacture.

 

[THC2LSD]

probably a great precursor but I don't think it's active.

 

[Epsilon Alpha]

If its active at any appreciable dose and avoids weird toxicity issues, then it would be an interesting chemical just from the immunological point of view. Monoamine transporters aren't too picky so long as there's a phenyl group and a nitrogen somewhere, so it might have some affinity for the NET/DAT.

 

[rakketakke]

probably a great precursor but I don't think it's active.

It's like amphetamine, the mental clarity but without the kick.

 

[Refluxer]

I was inspired by reading: "Improving immunogenicity and overcoming self-tolerance: by replacing strategically chosen tyrosines with p-nitro phenylalanine, a tolerated self-protein can be made immunogenic." (http://en.wikipedia.org/wiki/Expanded_genetic_code) I noticed that replacing tyrosine with p-nitro phenylalanine would just be replacing a hydroxyl (OH) group with an amino group (NH2).

1. Nitro is NO2, not NH2.
2. Haven't read the article you're referring to, but sounds like they are discussing alteration of proteins to make the immune system react on them. In an overwhelming majority of cases this is not something desireable. Quite the opposite actually.

If its active at any appreciable dose and avoids weird toxicity issues, then it would be an interesting chemical just from the immunological point of view.

In what way would it be interesting from an immunological point of view?

Monoamine transporters aren't too picky so long as there's a phenyl group and a nitrogen somewhere, so it might have some affinity for the NET/DAT.

There is a long way before a compound ends up in synapses. Even if injected it still has to cross the blood brain barrier in suffiecient amounts, and DAT/NET are quite picky when it comes to positioning of aromatic groups relative to nitrogen. IMHO at least. The compound discussed does not contain any nitrogen.

 

[Refluxer]

It's like amphetamine, the mental clarity but without the kick.

Really? You had a jar of 1-phenyl-2-propanol handy and had a taste?

In the article J.Pharm.Sci., 1971(60), 5, p.799 1-phenyl-2-propanol is reported to cause ataxia and sedation in mice. No hyperactivity was noticed.

 

[annonymous]

Really? You had a jar of 1-phenyl-2-propanol handy and had a taste?

In the article J.Pharm.Sci., 1971(60), 5, p.799 1-phenyl-2-propanol is reported to cause ataxia and sedation in mice. No hyperactivity was noticed.

ah, the voice of reason has entered. Good idea using a database to research, I'll have to search that name (along with the several others that could be used for this compound).
Good call on the nitro/amino thing (duh).

 

[MattPsy]

An amine is not necessarily required for DAT/NET activity. Look toward the tropane analogues for examples of this. I believe some MPH derivatives that have no amine also work. But yeah, this featured compound sure aint got it.

 

[Epsilon Alpha]

1. Nitro is NO2, not NH2.
2. Haven't read the article you're referring to, but sounds like they are discussing alteration of proteins to make the immune system react on them. In an overwhelming majority of cases this is not something desireable. Quite the opposite actually.



In what way would it be interesting from an immunological point of view?



There is a long way before a compound ends up in synapses. Even if injected it still has to cross the blood brain barrier in suffiecient amounts, and DAT/NET are quite picky when it comes to positioning of aromatic groups relative to nitrogen. IMHO at least. The compound discussed does not contain any nitrogen.

http://www.sciencedaily.com/releases/2005/03/050326001511.htm Methamphetamine produces an immune response in rats.
Also, the only thing I'm getting at is that DAT and NET aren't really picky for substrates. Hell I've seen a DRI that replaced the hetrocyclic ring in methylphenidate with a cyclopentane and it still bound with 1/3 the affinity.

Currently roadtripping and banging out this response between cell reception.