i was browsing the other day and came across something interesting, http://en.wikipedia.org/wiki/Tryptophol , "It has been first described by Felix Ehrlich in 1912. Ehrlich demonstrated that yeast attacks the
natural amino acids essentially by splitting off carbon dioxide and re-placing the amino group with hydroxyl. By this reaction, the tryptophan gives
rise to tryptophol", if we have tryptaphol can we just not esterify with toluenesulfonic anhydride and react with protonated dimethylamine? or if the
molecule is stable enough reflux it with iodine and react with protonated dimethlamine, sounds much more clandestine and easier to synthesize, my
question is will the rest of the molecule be stable enough to reflux with iodine?
[Edited on 10-3-2012 by rannyfash because certain words have been misconstrued]
[Edited on 10-3-2012 by rannyfash]weiming1998 - 10-3-2012 at 01:59
Are you actually asking for advice about the synthesis of illegal drugs?
And looking at what you posted: "sounds much more clandestine and easier to do", you just want to synthesize it, then smoke/inject it.
I do not think practical drug discussion is allowed here.rannyfash - 10-3-2012 at 04:03
i do not take illegal drugs or make them, im just interested in theoretical synthesis of molecules, reading through my post it does sound like you
suggested and i apolagize for that, although i also believe drugs can be very harmfull physically and psychologically is this not a science forum? do
we really discuss the morals? when i said "easier to do", i meant synthesis, as others depend on ketone catalysis of tryptophan in an anhydrous
environment to decarboxylate and then run a complex series of methylating steps involving strong reducing agents and watched chemicals, which i would
argue is considerably more complicated than my theoretical synthesis, i do not want to synthesise class A drugs, its purely theoretical, as for
practical, i have not listed specific practical steps with molar amounts or masses of chemicals required, or the equipment techniques or solvents
needed, i have just outlayed my ideas, i hardly think that this is practical
[Edited on 10-3-2012 by rannyfash]tastyphenome - 10-3-2012 at 05:35
Why bother when the Earth's plants produce untold Tonnes of this stuff a year? for fun?Bot0nist - 10-3-2012 at 06:41
Why reinvent the wheel? It is practically just a two step from tryptophan. Have you read Shlugin's write up? Other than the solvent, the reagents seem
pretty available.rannyfash - 11-3-2012 at 08:08
tastyphenome, because i am interested in the chemistry, bot0nist, can i have a link?Bot0nist - 11-3-2012 at 12:01
[Edited on 12-3-2012 by Bot0nist]ThatchemistKid - 11-3-2012 at 12:13
though I've never made this, generally methylating a primary amine like one would have to do starting with tryptophan is very difficult to stop at the
dialkylated derivative and usually gets alkylated to the trimethyl ammonium salt, I have read that ethyl groups provide a large enough steric
encumberance to hinder over alkylation though.rannyfash - 11-3-2012 at 16:26
thanks for the link bot0nist, i was hoping that reacting the 2-(1H-Indol-3-yl)iodoethane with dimethylamine wouldnt afford an ammonium salt with 2
ethanylindole groups, as you said with ethyl groups, they are large enough, in my method methyl iodide was never mentioned, what i was saying was
fermenting tryptophan along with sugars and nutrients for the yeast, purifying the tryptophol produced and refluxing it with phosphorus triiodide to
make 2-(1H-Indol-3-yl)iodoethane, i can then react this with dimethylamine, thatchemistkid, i think you are under the impression that i am talking
about methylating tryptamine, my only worry is the stability of the indole ring with phosphorus triiodide would using pcl3 minimise side reactions?ThatchemistKid - 11-3-2012 at 20:27
I was actually responding to the botonists post about reinventing the wheel, sorry I did not make that clear. What I was saying was that for dmt
specifically you would have issues going through the tryptamine route.rannyfash - 12-3-2012 at 00:01
greend: trivial as in synthesis? i assume as thatchemistkids comment on ethyl groups means it will prevent over alkylationGreenD - 13-3-2012 at 06:23
yes. although I've never heard a report of it working other than shulgin,
bromo ethanol + tryptamine with a base like diisopropylethylamine will give you the intended active.rannyfash - 19-3-2012 at 12:12
greend: im not sure that would give you det, i can see that the base is there to deprotonate the tryptamine so it becomes an nucleophile, but
bromoethanol?, do you mean bromoethane?
[Edited on 19-3-2012 by rannyfash]GreenD - 19-3-2012 at 16:35
woops yes bromoethane.pip - 21-3-2012 at 10:44
I've caught a few mistakes shuglin has made in his write-ups and some comments about THC analogs (delta 3 being abandoned when the n-pentyl chain
modifications were being investigated) but everyone makes mistakes. I think there is one in the dmt write-up, making the benzamide with acetic
anhydride? He must have meant benzoic acid anhydride but then again maybe mistakes are on purpose, to intentionally keep the uneducated from
succeeding. I know acetic anhydride is hard to find but I found some and I cant find benzoic acid anhydride or p2o5 to make it (or P to make that) so
just maybe it is on purpose.
If shuglin says it its probably true but if you actually follow the synthesis and don't know how to spot mistakes in write-ups you will waste time,
money, and may harm yourself or others. (I know O.P. isn't going to do this but many more people read these forums than post in them and this site
has its fair share of untrained hobbyists and naturally some may have different morals than we may wish)boyle - 8-5-2012 at 05:46
First post here, and I want to abide the rules of a forum as excellent as this but I'm afraid my first post is going to break the cardinal rule of
all, begging for more than it gives.
I toyed with asking these questions somewhere else, or maybe starting a new topic, but finally decided that this topic was already close enough. What
follows then are some very basic organic chemistry questions, and I'm hoping maybe some of you might be willing to help me with them. Please
feel free to respond with nothing more than links to any relevant introductory texts online, as I hope you will give me the benefit of the doubt
regarding my own searching out of this before hand. What I'm hoping is that in between the lines of my ignorant questions, the specific areas in
which I am in most need of more education will shine through, and I hope that it is alright for a beginner to proceed in this way.
Regarding the decarboxylation of amino acids like tryptophan and phenylalanine. Why is it that simple pyrolysis isn't sufficient? I'm aware of
the named reactions online which involve the suspension of these compounds in tetralin in the presence of a ketone. But why tetralin, would anything
else work just as well? Again, too, why a ketone, are keytones just known for their ability to agitate carboxyl groups away? What sorts of reaction
mechanisms should one seek out for a better understanding here, that is, with respect to the decarboxylation of amino acids like tryptophan,
phenylalanine, tyrosine, and their already hydroxylated substitutions? (I can find much on the subject of decarboxylation reactions, just not much on
the subject/logic behind synthetic decarboxylation of amino acids!).
Regarding the methylation of the decarboxylated amines which would be yielded through what I was asking about in the first question. Why is it
that this can't be accomplished using one of the usual suspects like DMSO in the presence of a simple base? I'm assuming it has to do with the
relative complexity of, e.g., a tryptamine or a phenylethylamine, but I can't seem to find anything online which would give a direct answer to this
more-or-less direct question. (Again, lots about methylation in general, and/or methylation as it pertains to biosyntheses, but nothing much on the
logic/subject of the synthetic methylation of tertiary amines. What I'm looking for here, then, is a way into being educated enough to look
at whatever amine, as well as whatever potential methyl donor, and work out whether and/or how well methylation of the amine might work using that
donor... i.e., basic stuff!)
Finally, as I kept suggesting in the questions above, information about biosynthetic reactions along these is nearly limitless. So then is it
true that the extraction/isolation of enzymes is insanely difficult? And that they are insanely difficult to to work with? Is it really true that
one couldn't even begin to approach something like this with nothing more than a centrifuge, a suitable buffer, and suitable solvent?
There is probably no need to continue on with my baby-time questions, as, needless to say, I'd also be interested in the hydroxylations and/or
acetylizations of these compounds as well as the ability to determine which position these substitutions would be most likely made at in a given
reaction. Please believe me that I've gone about looking for all this specifically and had a hard time finding anything. Take Melatonin, for
example, why can't that be deacetylized using nothing more than simple hydrolysis? If it hasn't been made clear already, I guess what I'm really
trying to wrap my head around, and purely, of course, from nothing more than hypothetical standpoint, is why all the reactions listed online would
have us using things like "cyanoborohydride," that is, why they can't be accomplished using nothing more than your more garden variety
chemicals/processes. I hope that it was okay to ask in this way, and to any mods, please erase my post if it wasn't. GreenD - 8-5-2012 at 06:36
1. I don't really know. People tell me it is the formation of the imine (the amine + the high b.p. ketone) that makes decarboxylation easier and
(possibly) quantitative. I don't know why this would help, some kind of electron movement from the carbon to the nitrogen allows for the new C-O bond
(making CO2). Probably hard to understand what I mean, sorry.
2. I don't know. The problem in general with tertiary amines is how do you make sure you do not get a Quaternary amine? I guess you could just basify
the product and extract a tertiary amine, but I feel as if there are problems, but know little of the chemistry behind them.
3. Have you ever done this type of biological work? How do you isolate your target enzyme?
I have no experience with isolating enzymes, but from my understanding it isn't trivial. And if you don't know WHAT enzyme is actually doing the
methylation (or whatever else) you need a huge gel electrophoresis apparatus, to distinguish between them all, and then you isolate each (in small
yields) and you must test each enzyme, which could be thousands. But again, I have no experience, that is simply what I would expect the simple lab
would have to do.
