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Stimulants of the Future II

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It might still be worthwhile, but the 3,6-dimethyl makes a lot more sense if you have PPA to start from.
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Well, the 3,6-dimethyl has three stereocenters, thus giving eight different isomers, so good luck separating those...
 
It's cool mate! Happends to everybody.
Anyway thanks for pointing out the thing about nitrogen protecting groups, I completely forgot about those!
Maybe there's still a hope for beta-methoxy-methamphetamine to hit the streets someday.
 
There!! I finally found it again...geez it took me a while!

L&G I want to present to you a sweet & cute looking molecule:

RDS-127

RDS-127_structure.png


Haha it looks like a headless robot! Maybe we shold put some MD on it.

http://en.wikipedia.org/wiki/RDS-127
 
Why the hell is that the automatic suggestion for every freaking drug. It's a 5HT and DA agonist. Not a 5HT or DA releaser. Is the goal to make a cool new DA agonist?

btw- has a 2,5-dimethoxy-3,4-MD-amphetamine been made? My guess would be antagonist- that's almost a substitution at every potential spot.
 
Yes, 2,5-di-MeO-3,4-MDA has been made (from apiol) and assayed by Shulgin and also at the Hive.

It has an entry in PiHKAL.
The bioassayer at the Hive tried only 30 mg, at which level it is not active.
 
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Pihkal puts it's activity level somewhere around 60mg, IIRC.

edit: found it. It's called DMMDA.

Some vendor was going to put this on stock, I wonder how's that going... I hope they do, I'd definitely be interested in sampling this one...

Just check out this pihkal comment:

(with 75 mg) This was equal to somewhere between 75 and 100 micrograms of LSD. I was caught up with the imagery, and there was an overriding religious aspect to the day. The experience had an esthetic value. I liked it.
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I wish they would stock 2-MeO-4,5-MDA (from sesamol).

"It is much like MDA. I am into it."--PiHKAL
 
dread said:
Well, the 3,6-dimethyl has three stereocenters, thus giving eight different isomers, so good luck separating those...
Click to expand...

Well, the point is that starting from PPA, you'd already have two of the stereocentres sorted out, at least relative to each other. Racemic PPA would produce the (desired?) cis enantiomers only, whereas optically pure PPA (+ or -) would produce the (+)-cis or (-)-cis only. (To get the trans enantiomers you'd need cathine, but that's another matter.)

Of course you'll still have the third stereocentre at the 6-methyl, which may or may not be significant for the activity. I suppose you could deal with this one by using the appropriate and optically pure chloropropanol. In other words, a stereospecific synthesis of the 3,6-dimethyl may not be that difficult, really.

The 3-ethyl, on the other hand, cannot be made from PPA and requires that you start from scratch with achiral reagents. Still, 3-ethyl could be the way to go if restricted access to PPA is an issue.

I don't have any first hand knowledge about the 3,6-dimethyl, as I clearly demonstrated by my numbering screw-up in my previous post. :o I'm well aware of the nomenclature and priority rules, but I was being a cocky bitch and I obviously can't count to six.
 
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The only human bioassay I know of aminotetralin ended up with a hospital visit. That's all I know about it.

Might as well try 2-aminonaphathelene while you're at it.
 
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From what I read 2-AT substitutes to amphetamine altough with 1/8th potency while 2-AD with 1/4th.

On an italian patent I found it sais that 2-AT is being investigated as a possible 'cardiac insufficency' treatment with good results.
 
I read that at the hive, but if you want to try some, go ahead.

You might want to investigate 2-aminonaphathelene while you're at it (somewhat seriously).
 
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Rectify said:
I read that at the hive, but if you want to try some, go ahead.

You might want to investigate 2-aminonaphathelene while you're at it (somewhat seriously).
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2-amino naphthalene aka 2- naphthylamine, great choice.... if you want bladder cancer

FFS
 
(1) that suggestion was only "somewhat serious"

(2) I didn't say use it every day for the rest of his life or anything like that

(3) I wouldn't touch it personally, not at this point in time anyway, especially after reading what I did about 2-aminotetralin

EDIT: I just read the wikipedia entry of 2-aminonaphathelene. Do not take 2-aminonaphathelene. It is a known carcinogen.

(but then why aren't naproxen sodium and duloxetine most likely carcinogenic too?)
 
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Thats a lot of editing...

Please dont take my post as a comback to yours, I am not a fan aminotetralin at all I was just pointing out what I read here and there.

I too have concerns about naphtalene as a carcinogen but that doesn't necessarily mean that anything containing a naphtyl group is carcinogenic.
Even benzene is known to be carcinogenic still innumerable compounds containing phenyl groups aren't.
 
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Rectify said:
(but then why aren't naproxen sodium and duloxetine most likely carcinogenic too?)
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You are comparing an aromatic amine with ethers. That is not the same, in particular not with respect to toxicity. Ethers can be cleaved metabolically to yield the corresponding alcohols, which are much easier to excrete renally due to higher hydrophilicity, and which also offer the possibility for glucuronidation, thus again enhancing solubility.

The toxicity of naphthalene-compounds was discussed in connection with JWH-015/08 here, too. The presumable counter-examples naproxen/duloxetine were mentioned, too. I recommend a look at this thread to get an idea what renders a naphthalene-moiety cancerogenic. Things aren't this easy. A naphthalene alone does not suffice for cancerogenic activity. It strongly depends on other present functionalities.

- Murphy
 
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as Murphy pointed out, the mechanism of the specific carcinogenic activity of 2-naphthylamine is well known, involving an N-oxidised metabolite binding to DNA.
It has nothing to do with the naphthalene moiety per se, there are a lot of structurally different arylamino biarylamino and polycyclic aromatic amine carcinogens.

There is a saying "a little knowledge is a very dangerous thing" which I think is appropriate here.
 
Well, the little knowledge I have of 2-aminotetralin gleaned from reading the hive is enough for me not to want to try 2-aminotetralin and to warn others at least cursorily. It may be a perfectly safe compound, but I wouldn't want to be its next guinea pig based on a single, terse second hand trip report albeit from a trusted username.

I fail to see how Alexander Pope's quote applies to that instance (i.e., abstaining from 2-aminotetralin based on scant, possibly untrue evidence poses no threat to me).
 
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