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Learning enhancement Shulgin patient

yaesutom

Bluelighter
Joined
Oct 15, 2000
Messages
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I just typed in Shulgin into this Patient search engine: http://ep.espacenet.com/search97cgi/s97_cgi.exe?Action=FormGen&Template=ep/EN/home.hts

came up with one from

The compounds of formula I when administered orally or parenterally in an effective amount produce learningenhancement in mammals. An oral dosage range of about 0.1 to about 0.5 milligrams per kilogram of body weight is a convenient dosage for producinglearning enhancement in mammals. However, in general, the particular dosage most suitable for a particular application, as might be expected, wi vary with the age, weight and general health of the mammal under treatment and the degree of learning enhancement required. After talking intoconsideration these factors and any other factors to be considered, one skilled in the art of treating diseases of mammals can readilydetermine theappropriate dosage.


1-(2,5-dimethoxy-4-methylphenyl)butan-2-amine is one of them among others in the patient,

attachment.php


They did a bunch of learning tests on rats.. dunno, wierd patient on these though.. ?
 

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by patient, do you mean "patent"? because... i think you do. Otherwise I dunno what you're talking about.
 
This compound doesn't appear on that erowid page linked above. None of those compounds account for the extension of the ethylamine chain into a butan-2-amine chain. it comes close to 2CD-DiEt, however again, this compound has two extra carbons coming off what would be the alpha carbon of 2c-d. In light of that, it's hard to determine its learning enhancement effects. Could be greater or lesser than those mentioned on that page.
 
moracca said:
Not sure, but it looks more likely to be Alpha-ethyl 2C-D

You are right, I apologize. I guess we all get one chance at the posting-while-stoned screw up ;). And yes, now that this is cleared up, this is indeed Ariadne.
 
^^ Yes your right :)

But how does one find a new class? One way is to kind of stumble into it as a side-line of human experimentation with new psychedelics. But it is really difficult to pick up the clues as to what will be a good anti-depressant if you are not depressed. This compound, to which I had given the name of ARIADNE as the first of my ten "classic ladies" (I'll say more about them later), was not really a stimulant of any kind, certainly it was not a psychedelic, and yet there was something there. It had been explored rather extensively as a potential psychotherapeutic ally by a friend of mine. He said that there seemed to be some value in a few of his patients who had some underlying depression, but not much of anything with the others. So, I decided to call it an anti-depressant. I had mentioned some of this history one time when I was giving an address at a conference on the East Coast, and my host (who happened to be the research director at a large pharmaceutical house) asked if I would send him a sample. His company did many animal tests, one of which showed that it was not hallucinogenic (a cat whose tail erected dramatically with DOM did nothing with ARIADNE) and another that showed re-motivation (some old maze-running monkeys who had decided not to run any more mazes changed their minds with ARIADNE).

So patents were obtained for the "R" isomer, the more effective isomer, covering its use for such things as the restoring of motivation in senile geriatric patients. And a tradename of Dimoxamine was assigned it, despite several voices that held out for Ariadnamine. But it didn't have what was needed to make it all the way to the commercial market

Many, many analogues of ARIADNE have been made, and for a variety of reasons. In the industrial world there is research backup carried out, not only for the discovery of new things, but also for patent protection of old things. Several dozen analogues of ARIADNE have been made and pharmacologically evaluated, and some of them have been put into the published literature. The major points of variation have been two: keep the 4-position methyl group intact, and make the variations on the alpha-carbon (propyl, butyl, dimethyl, phenyl, benzyl, phenethyl, etc.--an extensive etc.) or: keep the alpha-position ethyl group intact and make the variations on the 4-position (chloro, iodo, methylthio, carboxy, etc.--again, an extensive etc.).

Some of these analogues I had made, and sent in for animal screening. The high potency of DOB suggested the bromo-counterpart of ARIADNE. The making of this entailed the proteo counterpart, 1-(2,5-dimethoxyphenyl)-2-aminobutane. Reaction of 2,5-dimethoxybenzaldehyde with nitropropane in benzene in a Dean Stark apparatus with cyclohexylamine as a catalyst produced 1-(2,5-dimethoxyphenyl)-2-nitrobutene, which crystallized as orange crystals from MeOH with a mp of 47-47.5 °C. Anal. (C12H15NO4) C,H,N. This was reduced to the amine 1-(2,5-dimethoxyphenyl)-2-aminobutane with LAH in ether, and this gave a hydrochloride salt with a mp of 172-174 °C after recrystallization from acetonitrile. The free base of this compound was brominated in acetic acid to give 1-(2,5-dimethoxy-4-bromophenyl)-2-aminobutane which yielded a white hydrochloride salt with a mp of 204-206 °C following recrystallization from IPA. The isomeric non-brominated analogue, 1-(3,4-dimethoxyphenyl)-2-aminobutane was made and explored by the Chemical Warfare group at Edgewood Arsenal; its code number is EA-1322.

Several of the alpha-ethyl analogues of ARIADNE were N,N-dialkylated,
 
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