Phenylephrine -> Epinephrine

I was thinking about phenylephrine and I realized that phenylephrine is basically epinephrine with one less hydroxy group. Is epinephrine feasable for recreational use? I've heard of people using IV epinephrine but is that the only route? It seems as though conversion of phenylephrine to epinephrine would be relatively easy.

 

Its not easy.. that "simple" hydroxy group is bonded to an aromatic ring. You would need to go through several steps to get to that...

There are a few different methods, one involves using sulphuric acid like youve probably never seen used before (process called sulfonation).

The other, more commonly used method for the preparation of phenols involves
1. nitration
2. reduction of the nitro group via a not so easy hydrogenation step to obtain an amine
3. transformation of the aryl amine to form a diazonium ion salt
4. heat + sulphuric acid


This isnt feasible.. you're underestimating chemistry.


And not to mention the different directing properties of the substituents already present on the phenylephrine molecule... the alkyl chain will direct ortho/para to it and so will the hydroxy group.. this will give you a large mix of varying products with the newly introduced hydroxy group at almost all carbons of the benzene ring.. the highest yielding product will probably one with the newly introduced hydroxy group at position 2 or 5, not 6.. which is what you would want.

 

Hm. There has to be an easier way. Maybe phenylephrine could be broken into two or more parts which could be used in the synthesis of epinephrine? Also, couldn't one bind a protecting group to sites on the ring in which you would not want a hydroxy group?

 

What would breaking down phenylephrine do...? I dont understand what youre trying to accomplish with that.

And bind as a protecting group on sites in which you woudlnt want the hydroxy group? that means yoiu have tons of protecting groups you have to eliminate, its not feasible at all. I think you misunderstood me when i said youd have hydroxy groups all over the ring..

 

Eh. Just an idea.

 

Well I was just asking what you had in mind..

Discussions man.

 

Also, what would the byproducts be? Those in themselves could also be active.....

 

I don't think there is much (if any) recreational value to it. I drank a couple drops of pure epinephrine in solution. Imo, its not euphoric, its not really that differnt from eating some pseudoepinephrine cold meds. IVing it maybe different or with large amounts. Epinephrine is also common in some otc inhalers for asthma and I've never heard of anyone getting off on those.

 

Epinephrine is easy enough to get and not much fun anyway. Ephedrine from phenylephrine would be more usefull, but i've never seen a practical method. One was posted somewhere that looked great until someone noted that the final product was an alpha methyl short of amphetamine.

 

Does anyone else notice the similarities between phenylephrine with MDMA and MBDB, especially methylone?

 

Yes, theyre phenethylamine derivatives.

By products being active? If nitrogen gas, inorganic metals and maybe sulphate ions are active... lol

What? an alpha methyl derivative of amphetamine from an attempted synthesis of epinephrine from phenylephrine? Something doesnt add up here.

 

Acyl, nitrogen gas goes out. Inorganic metals and sulphate ions.... Hm. Inorganic metals could be removed by exposing an aqueous solution to a magnetic field. It's not quite thorough but an idea. Sulfate ions... Exposure to a reactive chemical which would create a nonhazardous derivative would be nice.... Possibly a reaction between HCl to produce H2 (g) + H2SO4 (aq). That acid could then be worked out another way. Iono, I really just want to stick it to the drug companies for changing the formula to a perfectly working decongestant to crap just to prevent drug chemistry which is still possible with phenylephrine anyways!

Btw, I know that they are substitued phens, I just meant the very similar structures other than the fact that they are related to phenethylamine.

 

Ooh, shit even better. Maybe there is a way that through the introduction of K+ ions from, say, KCl to the solution, K2SO4 would form which is insoluble in ethanol. Here's my theory:

1. Complete reaction
2. Remove metals via exposure to magnetic field
3. Evaporate H2O and introduce 80%+ ethanol solution
4. Add KCl to solution and remove K2SO4 via precipitation....

That's the best I can think of right now. I've always liked chemistry but never studied very hard. Heh.

 

Exposure to magnetic field? Evaporation?...

You're thinking too hard, the most youd have to do in a reaction like this is acid/base extractions.

Also, you have to clean up after every step.. you cant just leave the left over sulphate ions from the nitration step (sulphuric acid is used to create the NO2+ species), the metal catalyst from the reduction step, and the loads of other crap you may have used to dry solutions/etc left in the melting pot while you're completing the synthesis.

At the end of it, you would just end up with something that can be salted out of a solution.. this can be filtered and dried/cleaned as necessary.

I guess you could use a rotovap to strip any excess solvent from the product but whos got one of those lying around?

 

Alpha-methylphenethylamine is amphetamine, what is an alpha methyl derivative of amphetamine?

Exposure to a magnetic field to extract ions? Does that even work? You can't just have a bunch of negative SO4 ions floating around in water without anything positive, I'm not an expert but even if you could do it, I'd bet that would fuck the pH of your water hardcore. Maybe I'm missing something.

I think you could do something similiar to a full DMT extraction, as in make some phenylephrine freebase or HCL and have it disolve in some solvent that doesn't disolve your other ions. Or maybe you could add some salt that would form a two percipitates when mixed with the other salt in solution. Good luck finding that salt. Even better, depending on the freezing point of phenylephrine, couldn't you just stick it in the freezer?

I could probably pass a chemistry SAT II, but that's about the extent of my knowledge... i'm no expert.

 

POSTED TWICE BY ACCIDENT

 

No, no. He said that there would be inorganic metals percipitated in the solution. Magnetic fields attract inorganic metals.[/quote]

Yep, that's kinda like me. But I know a bit more in terms of org. chem that sat 2 chem doesnt cover.

So, lets find a way to make some drugs from phenylephrine!

 

why don't you make ephedrine?

phenylephrine is phenethylamine with hydroxy on 3 and beta and a methyl group stuck to N.

snag the OH on 3 and stick a methyl group on alpha... presto you got ephedrine.

 

Yeah, we could do that too. Do you have synth instructions? Also, that wouldnt yield much in comparison. 30 mg of phenylephrine would yield a little less than 30 mg ephedrine under an ideal 100% yield. This is a really small amount considering ephedrine's dosage levels. With 30 mg of phenylephrine would yield more than 30 mg epinephrine with ideal 100% yield. The amount of epinephrine administered during cardiac arrest is between 0.5 and 1 mg. That's relatively a lot of epinephrine.

 

well i mean you can buy ephedrine online.