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Author: Subject: theoretical amphetamine variants
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[*] posted on 18-11-2006 at 05:19
theoretical amphetamine variants


The analogy between MDMA and methamphetamine and their variants makes me wonder about similar molecules that differ only in the aromatic system. I am working on pyrrolealdehydes, and it seems that a lot of reactions can be achieved analogous to benzenealdehydes. Has anyone looked at a methamphetamine like molecule that has a pyrrole ring (pyridine, furan, thiophene, naphtalene, etc) instead? Depending on the precise action of the molecule on the brain, such molecules might be potent in unexpected ways, such as lobotomizing/killing you in a very efficient manner, or be another variant drug:D
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Nicodem
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[*] posted on 19-11-2006 at 04:07


You need to be more specific. Are you looking for references to just any 1-(heteroaryl)isopropylamine or, like you insinuate in your first sentence, to monoamine releasing (heteroaryl)isopropylamines? Is it OK if they have other activity as well?
For example 1-(indol-3-yl)isopropylamine has 5-HT2A/2C agonism in addition to some slight MAO inhibitory action, but I don't know if its monoamine releasing ability was ever confirmed. Several of its ring substituted analogues are also well known for psychedelic activity.
Several 1-(indol-1-yl)isopropylamines were reported of being 5-HT2C agonists.
Several patents indicate that the equivalent indazol-3-yl and indazol-1-yl versions have 5-HT receptor affinity as well.
1-(thien-2-yl)isopropylamine is long known for its stimulant activity and recently its activity in men was described. The tester described it as equipotent to amphetamine by dose, but distinctively different. Several halogenated 1-(thien-2-yl)isopropylamines were also evaluated for their MAO inhibition and serotonin uptake inhibition.
Pyridin-3-yl and 6-methyl-pyridin-2-yl isopropylamines were prepared but their activity in rats remains unreported, probably due to inactivity. Same goes for the 1-(furan-2-yl)isopropylamine.
Interestingly, the 1-(heteroaryl)isopropylamines that have great potential for being mixed monoamine releasers were never reported to my knowledge. I'm talking about benzofuran-5-yl and benzofuran-6-yl isopropylamines, though their 2,3-dihydro versions were found to be monoamine releasers (serotonine mostly). And also the benzoxazol-5-yl and benzoxazol-6-yl, the indole and indazole, and the thio versions of these all. But then again given that even the most obvious choice for a mixed monoamine releaser, the 1-(naphth-2-yl)isopropylamine, remains unreported, it is no surprise there is little interest in the mentioned heteroaryl modifications.
There is also a rich spectrum of psychedelic 1-(heteroaryl)isopropylamines reported in literature. Most recently, the famous "dragonfly" compounds. But even previously there were reports of 1-(5-methoxybenzofuran-3-yl)isopropylamine and its 5-HT2A affinity. If I remember correctly, the thio counterpart was also evaluated. Surprisingly though, the 1-(indol-4-yl)isopropylamines were never evaluated even though it is apparent from the structure activity relationship that they would be potent psychedelics.
If you allow the amine side chain to be the ethylamine and N-alkylated ethylamine then the spectrum of researched 2-(heteroaryl)ethylamines becomes really wide including mostly indol-3-yl derivatives, but also many others like benzimidazoles and even rare heteroaromatics like thienopyrroles, for example.

PS: References on demand. I don't have the time to compile all of them.

Edit: I have not seen references for 1-(pyrrol-2-yl)isopropylamine yet.

[Edited on 19-11-2006 by Nicodem]
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[*] posted on 19-11-2006 at 05:26


Interesting. The question is whether it is due to difficulty in synthesis that this has not been tried, or simply because its unlikely to work. If I understand correctly from your post (thanks a lot by the way) there is sometimes effect, sometimes not, hence a lot of potential.

What I am working at is the synthesis of functionalized heteroaromatics from aldehyde functionalities, and develop a high yielding procedure. Hence the interest in hive related science, because there is a plethora of techniques available that apply to aromatic aldehydes, with their differences well documented. This made me think of the analogous molecules of heteroaromatics or longer chain aromatic aldehydes (ie, a benzaldehyde with a methylpyrrole group on the para position and infinite variants thereon). It is a bit of my private project to apply this kind of thing to exotic isopropylamines, and I know next to nothing about clinical tests for molecules.
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[*] posted on 19-11-2006 at 06:09


Aside from that you want to make 4-heteroaryl substituted amphetamines starting from benzaldehyde, your post makes no sence at all to me. "Plethora of techniques available" - like what and for what?
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[*] posted on 19-11-2006 at 07:01


I mean that the amphetamine boys have investigated dozens of methods for aldehyde chemistry, and that the hive is a better resource than any textbook on this specific topic.
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[*] posted on 19-11-2006 at 07:53


Sounds groovy, go for it!



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[*] posted on 19-11-2006 at 07:54


So you are not interested in heteroarylisopropylamines? I wrote my review for nothing? Cloner, next time state your questions clearly and properly! I can't read minds.
As for the 4-heteroaryl-amphetamines, I have no knowledge. But in order to avoid further confusion, please state precisely whether you mean 4-heteroaryl-amphetamines, 4-heteroarylalkyl-amphetamines or amphetamine ring-condensed with heteroaromatics. (use a graphic representation if you can't use IUPAC)
State also what kind of activity (or pharmacodynamics) you want: stimulant (DA/NE releasers), emphatogenic (mixed monoamine releasers), psychedelic (5-HT2A agonists), narcotic (mu agonistic) and so on.
Without properly phrasing the question you can not get a proper answer. Or else the answer can just as well be "42".

Quote:
Interesting. The question is whether it is due to difficulty in synthesis that this has not been tried, or simply because its unlikely to work. If I understand correctly from your post (thanks a lot by the way) there is sometimes effect, sometimes not, hence a lot of potential.


What do you mean? In my reply I described that there was done A LOT on heteroarylisopropylamines and even much more on the heteroarylethylamines of various types of activity. There is even MUCH MORE that can still be done. The difficulty of synthesis has nothing to do with it. For example, 1-(naphtha-2-yl)isopropylamine is very easy to prepare and it would be expected to have empatogenic activity, yet there is nothing on its pharmacology in the literature. The same goes for the heteroarylisopropylamines, for example 1-(benzofuran-6-yl)isopropylamine is well worth researching yet it is not researched. This has nothing to do with synthesis but it has a lot to do with the fact that there are only a couple of labs in the world developing new monoamine releasers and they can't do everything. They have lots of other great ideas to check out first. As for the amateur researchers, it is well known that, even if they are not just methheads, they are nevertheless mostly just a bunch of lazy bastards that can't get their attention span a minute away from the well known and appraised, long time ago discovered psychoactive compounds.
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[*] posted on 19-11-2006 at 08:15


When I was working on epibatidine type molecules at university, naturally I used to search engine to see if any heteroaryl-IPA analogs had been made. Although this was not the case, I did see that 3-pyridyl analog had been made and as such is active. I forget the details now although I recall that some work had been done in this area.

^To the above poster, the napthyl analog has been prepared recently by a researcher known as Rothman. There is a lonk to his work upon a request I made in the reference section. However it must be stressed that the compound acts primarily as a serotonergic and as such, is a cowboy drug and not expected to be a hit with the indians.

Here is the link to the article. As we can see, there is not really anything fantastic here.

[Edited on 19-11-2006 by Drunkguy]
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[*] posted on 19-11-2006 at 08:35


Thanks a lot Drunkguy. :D That review rocks!

You are wrong though. According to that paper 1-(naphth-2-yl)isopropylamine is extremely cool no mater what the Indians and cowboys think. Its 5-HT/DA release ratio of 3.7 is just perfect. I went to check the 5-HT/DA release ratio for MDA (JMC, 36 (1993) 3700-6) and it is 3.7 exactly like our fellow naphthyl derivative! :) (though I used the IC50 ratio and not the release at the same concentration, but assuming linearity to some extent…)
But then there is also the NE to take into consideration and probably a bunch of other stuff. 1-(naphth-2-yl)isopropylamine might also have more than just negligible affinity to some 5-HT receptors.
Chances are that the 5-HT/DA release ratio could be slightly lowered by N-methylation for those who don't like to keep it that high. Though unfortunately on the account of the dose potency.

The paper also says that p-Me-amphetamine has a 5-HT/DA release ratio of 0.82 which explains why the guys who tasted it reported a kind of emphatogenic activity. I always suspected it was a mixed releaser. But it is interesting to se p-fluoroamphetamine having only negligible 5-HT releasing ability (just 11 times more than plain amphetamine). I expected a higher ratio for this compound. Too bad they did not also measure the ratio for p-nitroamphetamine that is supposed to be a very potent mixed monoamine releaser.

Edit: Rearranged the text to make more sense.

[Edited on 19-11-2006 by Nicodem]
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[*] posted on 19-11-2006 at 13:31


Great piece of paper Drunkguy, highly interesting!



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[*] posted on 22-11-2006 at 04:03


Nicodem, this is a very wide topic and your answer made a lot of things very clear even if the question was halfway unspecified.

My focus of research is very limited. I cannot invent ten thousand different wheels at the same time, so this is why I am specifically poking into the sequence aldehyde -> nitropropene -> amphetamine and try to apply it to heteroaromats. Such a variant i could make in a short time on pyrrole, if that nitrogen in the ring wouldn't be such a bitch. Also it is very likely that someone has thought it before, hence this post. Nonetheless, there are other potentially interesting variants which are worth discussing even if I am not going into the lab to actually do it tomorrow.

ummm and drunkguy could you pm me the password on that forum, it seems mine is a year out of date:D

[Edited on 22-11-2006 by Cloner]
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[*] posted on 22-11-2006 at 12:34


I would gladly give you more advices, but still I wander why you can't give such simple explanation as about what basic structure and what activity you want? (I don't read minds!)
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[*] posted on 23-11-2006 at 04:27


Consider amphetamine and keep only the side chain. Put another 6-ring or 5-ring or more complex ring in place of the benzene ring. What is the physiological effect of this molecule?

I admit I wrote this BEFORE thinking on it for a week, and I don't have the guts (or insanity) to try it out on myself and it'd end up on a shelf. However, I made dangerous stuff for the sake of making it before.


[Edited on 23-11-2006 by Cloner]
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[*] posted on 23-11-2006 at 04:39


Quote:
Originally posted by Nicodem
So you are not interested in heteroarylisopropylamines? I wrote my review for nothing?


I certainly found it interesting, and will probably come back to it in a while when I get the ability to do more advanced organic synthesis. All the compounds seemed unique and interesting, hence synthesis worthy.
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[*] posted on 23-11-2006 at 12:14


Thanks Chris.
Quote:
Originally posted by Cloner
Consider amphetamine and keep only the side chain. Put another 6-ring or 5-ring or more complex ring in place of the benzene ring.

So, you are interested in the 1-(heteroaryl)isopropylamines like you insinuated in the first post? Then after I replied you wrote "ie, a benzaldehyde with a methylpyrrole group on the para position and infinite variants thereon" meaning that you were interested in 4-heteroarylamphetamines which are something completely different. Please be clear and concise and use IUPAC nomenclature when talking about structures!
Quote:
What is the physiological effect of this molecule?

Huh! Which molecule?
Quote:
I admit I wrote this BEFORE thinking on it for a week, and I don't have the guts (or insanity) to try it out on myself and it'd end up on a shelf. However, I made dangerous stuff for the sake of making it before.

What dangers are you talking about? These compounds are fully legal and their synthesis is nothing dangerous at all (unless you are completely ignorant and clumsy). They are legal even in countries with such shady and irrational laws like the USA's "Analogue act" unless you are some asshole that wants to sell surrogate drugs on the street in which case you would deserve all the danger and the consequences. As long as they are made for research purposes, most governments would even encourage you, at least that’s what they do with the academic researchers. ;)




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[*] posted on 23-11-2006 at 15:09


Quote:
Huh! Which molecule?

1-(Thiophen-2-yl)isopropylamine and 1-(thiophen-3-yl)isopropylamine sound like obvious candidates.

PS: When discussing articles it would be nice if you would post the reference.
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[*] posted on 24-11-2006 at 00:24


Like I said, references are only on demand. I don't have the time to write full reviews, especially if I'm unsure that there is anybody interested, but I do have the time to give references for specific compounds when wanted.

1-(thien-2-yl)isopropylamine:

  • 1.) A pharmacological study on dogs, mice and rabbit tissue with the conclusion that it is similar, equipotent and equally lasting as amphetamine in its pharmacology. The authors tried the compound orally up to 50mg with no noticeable CNS effects (it includes the furyl analogue as well; authored by Gordon Alles himself!):
    J. Pharm. Exp. Ther., 72 (1941) 265.
  • 2.) Synthesis through the Grignard and Leuckart reactions and claims of sympathomimetic activity comparable to amphetamine while having a lower toxicity: US2367702 (1941)
  • 3.) Synthesis trough the alkylation of ammonia by 1-(thien-2-yl)-2-bromopropane: J. Am. Chem. Soc., 64 (1942) 477-480.
  • 4.) Synthesis by n-amylamine catalyzed Henry condensation followed by reduction with LiAlH4:
    J. Org. Chem., 15 (1950) 807-811.
  • 5.) Synthesis and effects on the locomotor activity of mice, LD50, effects on 5-HT uptake (including the chlorinated derivatives as well): J. Med. Chem., 21 (1978) 978-981.
  • 6.) Synthesis trough the alkylation of ammonia by 1-(thien-2-yl)-2-tosyloxypropane:
    DE2602846 (1976) and US4128561 (1978).
  • 7.) Some primitive tests on rats with barely any result analysis (including also several other 1-(heteroaryl)isopropylamines and 1-(naphtha-1-yl)isopropylamine): J. Pharm. Sci., 68 (1979) 591-595.
  • 8.) Synthesis from 2-thienylaldehyde using EtNO2 followed by Pd catalyzed hydrogenation: EP0069002 (1983).
  • 9.) Synthesis from 2-thienylaldehyde using EtNO2/AcONH4 followed by NaBH4/BF3/Et2O reduction:
    J. Med. Chem., 35 (1992) 280-285.
  • 10.) Syntheses by Henry condensation followed by reduction with LiAlH4: US5208252 (1993) and US5294621 (1994).
  • 11.) Sparse synthesis information but a full analysis information (HNMR, IR…; for the thien-3-yl analogue as well):
    J. Med. Chem., 46 (2003) 1512-1522.
  • 12.) Like the title "Heteroarylisopropylamines as MAO inhibitors" suggests, both thienyl isopropylamines as well as the furyl, benzothiophenyl, benzofuranyl and some brominated derivatives were evaluated for MAO inhibition activity (the Henry condensation is n-BuNH2 catalyzed): Bioorganic & Medicinal Chemistry, 13 (2005) 4450–4457.
  • 13.) Synthesis and human bioassay up to 40 mg by injection: "2-thienylic amphetamine isostere" (2005)


1-(thien-3-yl)isopropylamine:

  • 14.) See references 8, 10, 11 and 12.
  • 15.) Synthesis by n-BuNH2 catalyzed Henry condensation followed by reduction to the ketone with iron and then the Leuckart reaction/hydrolysis: J. Am. Chem. Soc., 76 (1954) 4466-4468.
  • 16.) A larger pharmacological study (locomotor activity in mice) including also other heteroarylisopropylamines (I have not yet read it): Arzneimittel-Forschung, 12 (1962) 902-7.


I left out a couple of patents and obscure references. Otherwise this is about all I can find on these two compounds. Let me know if there is a paper you can not obtain. I have them all but the reference 14.

[Edited on 24-11-2006 by Nicodem]




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[*] posted on 25-11-2006 at 20:54


I have heard that methyl groups on the benzene ring on an oxalone does not
destroy the euphoric effects of the compound.
what do you think about an indane ring instead.
this is just out of curiosity.




e3500 console login: root
bash-2.05#

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[*] posted on 27-11-2006 at 12:32


Wow, that's what I call service. :o Thank you, Nicodem!

Quote:
I have them all but the reference 14.

Which one?

I was thinking about a simple way of making the 2-furyl analogue:
furfuryl alcohol --(SOCl2)--> (2-furyl)-chloromethane --(1. Mg, 2. MeCN, 3. NaBH4)--> (2-furyl)-IPA
Unfortunately the chloromethane seems to be very unstable and I have no PBr3 for making the bromide. :(

Alternatively one could make the (2-furyl)-acetonitrile and the grignard with MeMgI, but my KCN and my PTC are planned for another experiment.

grumble, grumble...
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[*] posted on 27-11-2006 at 14:52


Quote:
Originally posted by turd
Quote:
I have them all but the reference 14.

Which one?


Sorry, that was a mistake after renumbering the references. I meant the reference 16.) Arzneimittel-Forschung, 12 (1962) 902-7. It should be in German and it discusses the pharmacological properties of various heteroarylisopropylamines.

1-(fur-2-yl)isopropylamine was also tested by Alles and Feigen (reference 1) and was found to be several times weaker than the thio analogoue in animals for most physiological activities and inactive in animal model of CNS stimulation (no locomotor effects in the same test where the thio analogue was active). Alles ingested 20mg and 50mg without effects. Feigen reported hints of stimulation at 20mg but then nothing at 50mg.

The furfuryl halogenides are all quite instable and I'm unsure they can be used in a Grignard reaction.




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[*] posted on 28-11-2006 at 15:48


by this compound (1-(thien-2-yl)isopropylamine) you imply thiophene substitution for benzene in say phenylisopropylamine?
I'm not too clear on the nomenclature.
thiophene rings follow huckel's rule?
on napthyl substituted isopropylamines they sound interesting i think you can try a direct synthetic approach where you could avoid formylation, henry condensation, and then reduction. say for exapmple you could go directly to ketone by conjugating acetone with it as in the p2p synthesis using Mn(III) acetate, acetone in acetic acid the napthyl-2-substitution is tantamount to the para position on the benzene ring right? because I think that process is para selective. (there is some confusion there too in one post it's listed 2-sub and the other it's 1-substituted) theres also other means involving organo zinc type reactions where you can tack on a methyl ketone to an aromatic ring and there's friedel crafts alkylation with chloro acetone (I would'nt recommend either because of the lacrymatory effects of halogented ketones might make this rather unpleasant process to deal with). you could do something similar with toulene to get the para methyl phenylisopropylamine you mention that has empathogenic properties. there's an abstract I read about 2,5 dimethyl amphetamine (you could use para xylene in this case) where it is said to have equivalent therapuetic value to amphetamine but less pressor side effects (high blood pressure, palpitations).
I could'nt access that article linked up there can someone help with this?
I curious if there has been human trials of the napthylisopropylamines. they sound like they have promise and avoid the legal implications of the analouge act.
another synthetic stategy involves friedel crafts alkylation of (whatever the aromatic is) with allylchloride and Fe(III)Cl this has the advantage that the allyl moiety will alkylate the ring and then the HCl produced by the reaction will add markovnikov to the double bond being catalyzed by the lewis acid. to give a direct intermediate(aryl-2-chloro-propane). you can then perform a finkelstein reaction on this with sodium iodide to get a 2-iodo intermediate which is the better leaving group.
I'm sure allyl bromide would be optimal for overall ease.
the problem in this scheme of course is multiple ring substitution, and reduced yeilds as a result.
oh and in the last post about benzofuranylisopropylamines, the thio analouge would be sulfur substitution in the furan ring correct?
in the case of thiphene-2-aldehydes as the proposed starting material to the thiophenepropan-2-ones would be aldol condensation with methylethyl ketone(catalysed by hydrogen chloride gas) and then oxidation of this to the propanone with performic acid (oxidation is a misnomer because hydrolysis also takes place)

[Edited on 28-11-2006 by jon]

[Edited on 28-11-2006 by jon]

[Edited on 29-11-2006 by jon]

[Edited on 29-11-2006 by jon]

[Edited on 29-11-2006 by jon]

[Edited on 29-11-2006 by jon]
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[*] posted on 1-12-2006 at 03:15


Quote:
by this compound (1-(thien-2-yl)isopropylamine) you imply thiophene substitution for benzene in say phenylisopropylamine?

Yes, a google search would have told you that in a few seconds.

Quote:
thiophene rings follow huckel's rule?

http://en.wikipedia.org/wiki/Aromaticity#Heterocyclics

Quote:
[...]

Interesting, but neither xylene nor naphthalene are heterocycles.

Quote:
oh and in the last post about benzofuranylisopropylamines, the thio analouge would be sulfur substitution in the furan ring correct?

I don't know which post, but yes, sounds correct.

Quote:
in the case of thiphene-2-aldehydes as the proposed starting material to the thiophenepropan-2-ones would be aldol condensation with methylethyl ketone(catalysed by hydrogen chloride gas) and then oxidation of this to the propanone with performic acid (oxidation is a misnomer because hydrolysis also takes place)

Mmh? Could you elaborate on that?
The aldehyde has 1 carbon in the side chain and MEK has 4. Even if you don't get a mess that makes a side chain with 5 carbon atoms, i.e. a pentane.
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[*] posted on 1-12-2006 at 22:58


a quick search on google yeilds many supplier's of thiophene-2-carboxaldehyde. available from ll over the world our slanty eyed friends are your best bet probably.
I can't find the reference right now I'll dig it up you get a methyl butene-ol via aldol condesation and baeyer-villiger oxidattion will give an ester derivative which will slpit off to a methyl ketone I'm sure of this.
It would be more convenient to catalylize the reaction with with sulfuric acid(in acetic acid) than to bubble hydrogen chloride gas into it, or on the surface it looks easier to do it this way.
ahh here it is!

Phenylacetone by Bayer-Villiger Oxidation of 2-acetyl-1-phenylprop-1-ene
Boeeseken & Jacobs
Recl. Trav. Chim. Pays-Bas 55, 786 (1936)

Peracetic acid treatment of 2-acetyl-propenylbenzene (3-methyl-4-phenyl-but-3-en-2-one) below 30°C resulted in the formation of phenylacetone enol acetate (2-acetoxy-1-phenylprop-1-ene), mp 131°C and bp 103°C/3mmHg. Heating the crude reaction mixture with aqueous HCl at 80°C gave phenylacetone.

For more information check the old Twodogs' thread from The Hive (post No 245942).
oh and not to split hairs where did I Imply napthyl rings were hetero cyclic? I only stated I was interested if there were any human reports of it's qualitative effects (the isopropylamines) It sure sounds tantalizing and best of all legal!

[Edited on 2-12-2006 by jon]

[Edited on 2-12-2006 by jon]

[Edited on 2-12-2006 by jon]

[Edited on 2-12-2006 by jon]
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[*] posted on 2-12-2006 at 08:29


I see... Baeyer-Villiger. That's a pretty clever synthesis strategy. I wonder if it works well - I'm a bit weary of pre-NMR and pre-GC/MS publications.
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[*] posted on 2-12-2006 at 13:33


I dunno ketones are pretty easy to characterize, without 1h-nmr or gc/ms it might be paydirt. it sure beats henry condensation it's easy to get mek, and hydrogenperoxide, and acetic or formic acid.
BTW would nicodem be so kind to translate that thread from hyperlab? I can't read cyrillic and I'm dying to know the subjective on the thiophene analog.
In what way is it distintly different from amphetamine?
here's where I'm confused gordon alles says it's equipotent to amphetamine in dogs yet tries it himself and reports no cns activity.

[Edited on 2-12-2006 by jon]
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