N&PD Moderators: Skorpio
Psychedelic aminoindan derivatives
As far as I understand, 2-aminoindan is a stimulant, 5,6-methylenedioxy-2-aminoindan is a serotonin releaser. Has there been any research into other aminoindan derivatives such as 4,6,7-trimethoxy-2-aminoindan (this would be the analog of TMA-2). Could they be psychedelics?
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dread
Bluelighter
I'm sure they could. Wasn't there already a mescaline analogue with a similar carbon chain? I mean 3,4,5-trimethoxy-(2-aminoindan). (the numbers may be off there, but you'll know what I mean)
A dihydrobenzofuran-analogue of the 2-aminoindan would also be interesting. Then add a 3,4-dihydrofuro-group there and it would look nicely symmetric...
Hammilton
Bluelighter
For some reason I doubt they'll be psychedelic. Serotonin releasers, maybe, but not psychedelic. I'm pretty certain that nichols looked at these, and MDAI has definitely been studied (mice generalized, but only partially, IIRC).
As I look at it, and this is worth little, the nitrogen will be mis-located. As I recall, indene analogues of tryptamines have been synthesized and had some but minor activity (whereas, again, from memory, the benzofuran analogues of tryptamines had similar activity). I would think that having the shape similar to all of these would mean it'd need to bind in a similar way, which would locate the amine totally in the wrong place.
Then again, the TCB's are potent, if underwhelming psychedelicly.
And then again again, my memory is piss poor, so maybe this is worth one cent.
dread
Bluelighter
Then how about 1-aminomethyl-indan?
Limpet_Chicken
Bluelighter
Ey hammy, 2-AI isn't anything to write home about really, nothing shit, but nothing fantastic either, although since I obtained a gram for 20UKP I cannot really complain, the price of an 8th of herb weighed against the chance to check out something novel, I'm usually game for that
I found orally it did little except induce insomnia/wakefullness, fairly long acting, nasally burns like absolute fury, ok rectally or IV.
I have a trip report or two about it on erowid somewhere actually.
Had too much peripheral tweakyness to me, how does it act, out of interest?
That said, that is my personal opinion of it, and my adrenals give me absolute hell also, unless beaten into submission with opiates and/or A2 agonists.
Oddly, I found it quite a good painkiller, I have a longstanding knee injury, which recently got made a ton worse by surgery that IMO feels like it got buggered up, wasn't so bad then but still affected my walking any distance, and it actually did stop most of the pain, I recall being quite impressed by that, given that I'd usually take around 300-500mg DHC to deal with it on a bad day.
Not much of a comedown either, certainly not like phet, which to me has the foulest comedown of anything I've ever tried (save one party perhaps involving too much MDMA, 3g of pretty lethal whizz 'base' , 2 bottles full of ether, copious booze and yopo snuff, but thats better left for another time entirely)
BUT, I found it almost impossible to overpower with benzos, 52.5mg nitrazepam and 25mg promethazine failed to allow sleep, and at the time, I had no tolerance to little tolerance to benzos, and that much moggie would have absolutely pasted me for a few days had I not been at the tweak.
Bear in mind though, that I have some kind of adrenal squirrelyness going on, and more or less continuously feel like I just got a smallish dose of epi, and am VERY sensitive to stimulants, indeed, pretty much intolerant to any but microdoses of amphetamine type stimulants, and require much lower doses than anybody else I know of DARI-type stimulants (at least my charlie lasts longer, given one line is almost too much)
I wouldn't mind trying the n-ethyl homolog though, I don't know as its ever appeared on the market, but would be fairly trivial to produce from 2-AI itself, if the SAR for aminoindans is anything similar to amphetamines, I'm not much of a stimulant fan, but N-ethylamphetamine was quite superior to both methamp and phet itself.
http://www.erowid.org/experiences/exp.php?ID=49701
http://www.erowid.org/experiences/exp.php?ID=52503
http://www.erowid.org/experiences/exp.php?ID=49250
How does plain 2-AI act? is it an amphetaminergic (is that a word even?) or DARI?
Come to think of it I might have to track down the source I obtained it from, since it was so cheap for an 'RC' and have a tinker with n-alkylated derivatives.
Edit: and SERIOUSLY do not snort the stuff, it feels like what, from an observers viewpoint, someone getting a brick in the mush looked like they felt.
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egor
Bluelighter
Any updates on MDAI or MMAI?
Beenhead
Bluelight Crew
Yeah, if the nitrogen has anything to do with a H-Bond in the active site, with everything else being in the same locale, it would be difficult to bind, and if it did, the shape of the subtrate complex would surely be different
UnfortunateSquid
Bluelighter
Unless I'm mistaken, 2-AI and MDAI should only have the one enantiomer each, as the molecules have a plane of symmetry, making the mirror images superimposable...
Beenhead
Bluelight Crew
plane of symmetry means meso, therefore no enantiomer
UnfortunateSquid
Bluelighter
That's what I meant, I may have used the word enantiomer when I meant isomer, though.
Beenhead
Bluelight Crew
^ Actually the more I look at the molecule, it could very well bind, since the Nitrogen is prety muc hin the same place, it just much less mobility.
it is generally considered with PEA's type materials that for decent 5-ht2a agonism that the nitrogen needs to be out of the plane of the benzene ring.
In these indans where the nitrogen is attached directly to the indan ring rather than having a 1 carbon spacer the nitrogen is in the plane of the ring. the methylamino compounds (with a 1 carbon spacer) are active agonists.
I am pretty certain some of the methoxy tetralins and indans with the DOM substitution pattern have been made by a canadian group and were essentially inactive.
V
ungelesene_bettlek
Bluelighter
but is not already the 5-ring in indan out of the plane of the benzene ring, at least a bit?
you mean, with an additional carbon between the nitrogen and the indane, so that there would be three carbons in total between the benzene and the nitrogen?
dread
Bluelighter
No, he means compounds where the aminomethyl group is in the 1-position on the indane.
http://en.wikipedia.org/wiki/Jimscaline
hamhurricane
Bluelighter
well jimscaline pretty much answers the question. it seems there is an entire world of incredible psychedelics which will surpass the classic PEAs in potency based off of the jimscaline structure. i wonder what happens when you substitute indole for benzocyclopentane in jimscaline (or in MDAI for that matter)?
also i find MDAI to be highly psychedelic, it is visually on par with with a high dose of 2C-D and it produces strong psychedelic ideation - even if it has no affinity for 5ht2 receptors is it possible that 5ht efflux indirectly agonizes 5ht2a? or could it activate the same second messenger system?
dread
Bluelighter
Doesn't work. Indole is aromatic, so the amine won't be in the same configuration... it would be too close to the plane of the aromatic circle. Indane works, because the cyclopentane is an aliphatic ring, which allows the amine to be further away from the benzene ring.
For MDAI, the same reason... you would have 2-amino-indole. Amines directly connected to an aromatic circle are a bit iffy, the compound would probably be toxic. And lack activity, because the amine would be exactly in the same plane with the indole.
nonbeliever
Greenlighter
Apologies for being slightly off topic, but wouldn't removing the nitrogen from MDAI to get 5,6 methylenedioxy indane (?) and adding CH2NH2 at the 2 position (the same as in Jimscaline) give you a very nice molecule indeed? Sorry its been a long time since Iv had to do any naming, and I suspect the numbering may change.
any major dude
Bluelight Crew
I would guess that though MDAI itself may have no affinity for 5ht2 receptor sites, serotonin, which it releases, most certainly does. I suppose its also remotely possible a vendor spilled some 2c-d in your MDAI as well... who knows
I'd been unable to find any human bioassays of TCB's. I remember from a Nichols et al paper that TCB-2 produced the "head twitch" in rats that usually correlates to psychedelic activity in humans. So they're underwhelming eh? That's kind of a disappointment. Regardless, I'd like to read any human bioassays/trip reports if you could remember where you found them.
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