Enantiomer
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Workaround?
Please forgive me if I make mistakes in how or where to post/ use this discussion board or if I have overstepped my bounds regarding content (please
offer any relevant feedback regarding use of the board – I would sincerely appreciate it). I have never actually used a discussion board and am
unfamiliar with the protocol. I have, however, been reading this board for quite some time now (in the order of years) as well as other boards (when
they used to exist). I guess I was always too worried about things, be they as they may, to actually participate. Now, there is a burning question
which someone feels needs an answer. Perhaps I should have started out more lightly in hopes of actually getting some response – I don’t know.
Going lightly has never been my thing, really. What follows may be of interest to someone, and I know there is at least one person in this world who
would love to find out if there is a solution. Read on . . .
A very interesting article was recently come across (yes, some people look for information from all possible sources – as I’m sure some of you all
do).
(http://www.justice.gov/dea/programs/forensicsci/microgram/jo...)
It talks of the reduction of phenylephrine (a replacement in cold medicine/ allergy formulations) and shows the result.
Below are molecular structures of the stating material compared to (one of) the original starting materials (if they will render on this board
correctly).
Compare . . .
Phenylephrine (mw = 167.1)
to . . .
Ephedrine/Pseudoephedrine
The only difference is a single molecule (a hydroxide on the phenyl ring).
But wait . . .
Using the same rxn/ rxns that have traditionally been used to reduce the latter of the two molecules above, what is produced is . . .
3-Hydroxy-N-methylphenethylamine
“Reduced Phenylephrine” (mw = 151.1)
The only difference is a single molecule (a hydroxide on the phenyl ring).
Interestingly, the article claims that the rxn producing: 3-Hydroxy-N-methylphenethylamine “Reduced Phenylephrine” is “facile” which is to say
easy (almost impossible to screw up) and that complete conversion was accomplished within only 30 minutes with “no byproduct”.
Now, what if there were a way to easily and inexpensively reduce the hydroxide molecule from the ring using (preferably) otc materials or other easily
obtained materials? What would you end up with (a rhetorical question – since it’s so obvious).
Is there any advice or even starting points for information out there that may help to solve this problem? Perhaps, some protective group must be
added to the side chain before attempting reduction of the hydroxide . . . Perhaps the hydroxide must be removed either before or after the reduction
. . . I don’t know. It would be very interesting though to find a solution (as I’m sure you can imagine).
Attachment: Microgram Journal, Volume 3, July-December 2005.pdf (383kB)
This file has been downloaded 3104 times
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turd
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Uhhhh....
This is totally useless if you want to make methamphetamine (your post isn't clear on that).
1) Removing a phenol (hydroxyl on the "ring") is not easy.
2) You would obtain N-methyl-phenethylamine, NOT N-methyl-amphetamine, which you could much easier make by methylation of plain old phenethylamine
(see other posts on that subject).
But good to see that after 20 years they finally start to grow some common sense and regulate ephedrine instead of Pred/I2.
PS: You're confused about the meaning of the word molecule.
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Nicodem
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Quote: Originally posted by Enantiomer  | | Now, what if there were a way to easily and inexpensively reduce the hydroxide molecule from the ring using (preferably) otc materials or other easily
obtained materials? What would you end up with (a rhetorical question – since it’s so obvious). |
Yes, there are a couple of methods to deoxygenate phenols, but all would require more than one step starting from
N-methyl-2-(3-hydroxylphenyl)ethylamine and all would require reagents that are several times more expensive than N-methyl-2-phenylethylamine. It
would however be an excellent challenge as it would become known as the most idiotically irrational synthesis of such a cheap product. I doubt anybody
could come up with a more complex and difficult route to such an easy target without explicitly trying. If you ever manage to make something like this
you might actually become famous.
| Quote: | | Is there any advice or even starting points for information out there that may help to solve this problem? Perhaps, some protective group must be
added to the side chain before attempting reduction of the hydroxide . . . Perhaps the hydroxide must be removed either before or after the reduction
. . . I don’t know. It would be very interesting though to find a solution (as I’m sure you can imagine). |
The easiest (or hardest, depends from person to person) is to UTFSE. Already on this forum there is referenced at least one or two methods for
deoxygenation of phenols (not that there are any more than one or two existing anyway). In Org. Synth. there is at least one method
thoroughly described.
Also, please learn how to use chemical terminology. Help yourself with some chemistry schoolbook - usually they explain terminology on the way.
Hydroxide is an anion. What you mean is hydroxy group. Molecule is a discrete minimal unit making up a compound. A functional group can therefore not
be called a molecule, being itself just a structural element of a molecule.
…there is a human touch of the cultist “believer” in every theorist that he must struggle against as being
unworthy of the scientist. Some of the greatest men of science have publicly repudiated a theory which earlier they hotly defended. In this lies their
scientific temper, not in the scientific defense of the theory. - Weston La Barre (Ghost Dance, 1972)
Read the The ScienceMadness Guidelines!
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Ozone
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“It would however be an excellent challenge as it would become known as the most idiotically irrational synthesis of such a cheap product. I doubt
anybody could come up with a more complex and difficult route to such an easy target without explicitly trying. If you ever manage to make something
like this you might actually become famous.”
Possibly the greatest...quote...ever.
 ,
O3
-Anyone who never made a mistake never tried anything new.
--Albert Einstein
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Enantiomer
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Thank you - your advice is apprciated.
Thank you all for your excellent criticism, I consider it very valuable. I will definitely take the advice to heart.
I know I need further education/ knowledge in basic chemistry to build a stronger foundation and I do intend to do some more studying.
So far my background is only one quarter of first year general chem (inorganic), chem 100 and physics 100 + maybe 10 or more years of self study (but
this is a little different than foundation stuff since it's always been in specific areas of interest).
The question I asked about was pretty much a guess, you could say, I just happened across something, thought it was interesting, and wondered about
it.
I'll definitely spend some time going back to basics and trying to build my knowledge a bit so I (hopefully) don't make as many mistakes with
terminology and such and will be able to participate on a higher level in the future.
In the mean time I would still like to be active and participate on this board (to the best of my ability). Please be patient with me as I also learn
my way around using a discussion board.
[Edited on 17-8-2010 by Enantiomer]
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chemrox
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@turd: what is pred/I2 ? you imply the regulation of ephedrine is a good thing. Similar rationale would make regulation of Na2CO3, dihydrogen oxide
and acetone also good things. My solution to the (unstated) problem is to make ephedrine hcl, HI and ether available at the stop & robs for cheap
prices. When the dust settles we can work with the ones left standing.
"When you let the dumbasses vote you end up with populism followed by autocracy and getting back is a bitch." Plato (sort of)
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turd
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Sorry, I was unclear. I meant red phosphorus (P(red)) and iodine (I2). Of course I don't think regulation of ephedrine is a good thing, but it seems
much more sensible to control a precursor to your "problem" which is merely one atom(!) away than chemicals which can be used for a myriad of other
things. Regulation of phosphorus and iodine has always struck me as one of the most idiotic decisions by the drug paranoiacs. More so given that most
of the world lives pretty fine without OTC (pseudo-)ephedrine and doesn't miss it.
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Lambda-Eyde
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This is not a meth forum. Please fuck off.
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Nicodem
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And what was that about? Next time, before going berserk, at least read the whole thread. The topic in not about meth, but about the synthesis of
N-methyl-2-phenylethylamine, which is neither illegal or any kind of a drug. The only connection with meth is the use of red phosphorous and iodine
for the reduction of the benzylic alcohol function. Contrary to popular belief this is a reaction that can be used for other than illegal purposes!
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Enantiomer
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In Over My Head?
Thanks Nicodem:
| Quote: |
And what was that about? Next time, before going berserk, at least read the whole thread. The topic in not about meth, but about the synthesis of
N-methyl-2-phenylethylamine, which is neither illegal or any kind of a drug. The only connection with meth is the use of red phosphorous and iodine
for the reduction of the benzylic alcohol function. Contrary to popular belief this is a reaction that can be used for other than illegal purposes!
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I've been thinking . . . perhaps I'm in a little over my head here. I mean, I do appreciate 'constructive' criticism and will make use of it all. I'm
a little concerned though about my ability to follow some of the discussions. I readily admit that my chemistry knowledge is limited but I do love
chemistry and its not something I intend to give up on.
Like I mentioned before, I've been reading this board for years before joining the other day; and, from what I've seen, there seems to be a wide range
of poeple participating here (people with varying levels of ability and knowlege). Many folks on this board seem to be very knowledgeable and skilled
(which is something that gives me a great deal of respect for this site and the people on it). In the end though, maybe I better get some more
studying in before I jump into using the board.
Another concern I have is not really being familiar with using a discussion board. I can forsee several mistakes I could make in regard to using a
discussion board that may not be taken lighly by some (like posting in a wrong thread, starting a new thread that happens to already exist under a
different title, not realizing that information I'm asking about is already addressed somewhere else, etc, etc.). Thanks again for all your imput
guys. I'll be around; and, in the menatime, studying up.
[Edited on 18-8-2010 by Enantiomer]
[Edited on 18-8-2010 by Enantiomer]
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Globey
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To me, phenylephrine looks more like tapentadol than ephedrine does. Of course, they are all different. I wonder weather phenylephrine has weak
and(or) ultra short lived mU activity. Extending the side chain by one carbon is preerquisite, just as is for phenylethylamine (for it to have any
chance against our bodies' MAO).
http://en.wikipedia.org/wiki/File:Tapentadol.svg
http://upload.wikimedia.org/wikipedia/commons/thumb/9/90/Phe...
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zed
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The Microgram journal is a good resource. Usually, they are very cautious about revealing compromising information. They tend to parse their words
carefully.
Only occasionally, do they really let loose....and hint at some arcane synthetic route, or material..... that chemistry buffs are generally unaware
of.
Catch Microgram while you can. During the "repressive" Bush years, the DEA began allowing access to a "public" version of the formerly "restricted
access" publication.
Recently, under the current "more open" US administration, the Microgram format has been revised. On my most recent visits to their website, there
has been nothing worth reading. Poof, gone! Those former, "public" Micrograms are still accessible, but they could disappear from the website at any
moment.
I will try accessing with another computer. Maybe, my archaic
PC, is just too weak to navigate their site.
[Edited on 19-8-2010 by zed]
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zed
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Well, I tried accessing the Microgram site with better hardware. The informative Microgram Journal of the last few years, is indeed gone.
In Jan. 2010, the DEA's "Iron Curtain" of secrecy re-descended. Public access to drug enforcement information, is no more. The show is over! Once
again, "real" Microgram access, is only available to Law Enforcement types.
Too bad. This revival of utter in-decipher-ability is a disturbing development.
If you want to peruse past issues. They are still posted....as of today. They could however, be liquidated at any moment.
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