The Big & Dandy Psychedelics of the Future Thread

[fastandbulbous]

A is effectively the benzopyran equivalent of the tetralins (tetrahydronapthylene) which are not active as hallucinogens because of the restraint of the PEA sidechain - can't put the nitrogen where it needs to be for binding - probably a dopamine agonist

C shows the tranylcypromine analogues of the psychedelic amphetamines. I believe they are serious MAOIs like their parent compound (the DOM analogue mentioned in PIHKAL is a MAOI)

D is known and doesn't have the dopaminergic 'kick' that's needed. More serotonogic - moreso than even IAP

H should be the 5,6-substituted furan ring (O on the 5 pos) to be a dragonfly like structure

[Psychedelics_r_best]

Even though these are not too creative, what would one think of 5-MeO-Allyl (edit)lIsoPropylTryptamine? Or any of the various possible allyl (edit) tryptamines, such as 4-Ho-iPALT, 4-Ho-EALT, etc ?

I bet iPALT compounds will be good.

[morninggloryseed]

What do you mean? There are many alkyl groups (methyl, ethyl, propyl, etc.) There is no such thing as 5-MeO-AlkylIsoPropylTryptamine...or rather that name would refer to any N,N-dialkyltryptamine which contains an isopropyl and another alkyl group.

Are you refering to a mono-alkyl tryptamine (such as N-isopropyltryptamine), a dialkyltryptamine (N,N-di-isopropyltryptamine), or are you just very confused as to what 'alkyl' means?

[Helios.]

Dude I'm sooo high,
You want 3-MeO-Methamphetamine aka Meow Mix powder/pills.

[djfriendly]

Because he abbreviated it "AL" (ala DALT) I suspect he meant allyl and not alkyl. I also suspect the answer to your last question is yes.

[Psychedelics_r_best]

Yeah, I meant allyl, not alkyl. Opps.

[morninggloryseed]

In that case, I agree. Especially something like N-methyl-N-allyltryptamine.

[fastandbulbous]

Yep; a carbon with a double bond to another carbon will not form a stable amine as tautomerization will result in a resonance between the amine & the imine (as happens with keto-enol tautomerization), but the imine isnt particularly stable and has a tendancy towards hydrolytic cleavage. This effectively means that a vinylamine will convert to a lower order amine (tertiary -> secondary; secondary -> primary) and acetaldehyde. I'm not aware of any imines of tryptamine that is stable except under very special circumstances (eg totally anhydrous, under nitrogen at at bloody cold temps), but if anybody knows of any I'm always open to learning

[Psychedelics_r_best]

Your speech confounds me. Are you giving reason to the fact that these compounds might, or probably won't be interesting?

Your knowledge of chemistry really leaves your speech with nothing I can understand.

[Dondante]

^^He's just saying that a vinyl substituent on the nitrogen would not work (it's not stable enough), but having an allyl would be just fine.

[Helios.]

Some crackhead on the streets tried to sell me some 4-allyl-2,5-dimethoxypenethylamine the other day. Said it was the same as methamphetamine.

I doubt it, but don't see why it wouldn't be active, or why the DOAL form wouldn't be stronger than the 2CAL form.

[Vanadium]

He says that vinyl amine is not stable.

Enamines and imines are interconvertible and we can't know if the molecule is a vinylamine or an imine beacause the electrons are constantly moving ; the molecule is both. The problem is that imines react with H2O to give a carbonyl (here, like fastandbulbous said, the vinylgroup is transformed into acetaldehyde).

this case is called "tautomerism" http://en.wikipedia.org/wiki/Tautomer

I thing the fluoro-alkyl groups are maybe interesting.

bis(2-fluoroethyl)-T
or bis(2-fluoroethyl)amide of lysergic acid !

[Helios.]

You have just defined the world tauteromerism incorrectly.
Any body tried 2C-allyl yet?

[Psychedelics_r_best]

I see, the picture enlightens me.

[fastandbulbous]

I did post explaining why you can't get N-vinylamines but it seems to have disappeared. N-vinylamines (or anything where the carbon the nitrogen is attached to has a double bond to another carbon atom) will rearrange to the imine structure (tautomerism a la keto-enol), which isn't too stable and is inclined to undergo hydrolysis to a lesser amine (ie secondary to primary) and a C=O bond; N-vinyltryptamine would very quickly become tryptamine and acetaldehyde

[fryingsquirrel]

I'm probably writing this wrong, but N,hydroxy N,methyl alphamethyphenethylamine might be a big seller. Might attract alot of unwanted attention.

[morninggloryseed]

^^^^

THat would be the "FLEA" analogue of methamphetamine. Don't think any authorities would put up with that for long.

[Helios.]

How long do you think they'll put up with 4-AcO-DMT?

[fastandbulbous]

It's pre-illegalized for the UK! (added to the CD list a while ago)

[Psychedelics_r_best]

^Well, your description of this vinylamine degradation doesnt apply, though, to an allyl chain because the carbon atom attatched to the nitrogen does not have a double bond to the next carbon in the chain, right?

[morninggloryseed]

Correct. Two carbons are in front of that double bond. That is why DALT (n,n-diallyl-T) exists while 'divinyl' tryptamine does not.

[fastandbulbous]

Well, your description of this vinylamine degradation doesnt apply, though, to an allyl chain because the carbon atom attatched to the nitrogen does not have a double bond to the next carbon in the chain, right?



Correct. Two carbons are in front of that double bond. That is why DALT (n,n-diallyl-T) exists while 'divinyl' tryptamine does not.

'Once a teacher, always a teacher' appears to be somewhat true in my case. Right class, for doing so well you can all treat yourselves to the psychedelic of your choice (that feels wrong just thinking/writing it as in my mind's eye all I can see is one of my old form/registration classes!)

The thought that someone I taught might be a BL is quite unsettling really

[hugo24]

N-Methyl-N-allyltryptamine,this is our classic MALT.Might have some GABA-ergic side-effect :)

Seriously,it might be as good as MPT.But so far we have no clear science if the allyls versus the propyls are interchangeable or are of quite different nature.Theres a MPT thread btw on ADD,unfortunately labeled as "MPT inactive?".

Since I'm back online again (hey,for about a month they couldn't fix my net connection on my new home...),I can follow the discussion again and post more regularly hopefully.Somewhere in a box are my notes about the 2. experiment with MPT,quite a success.Who woulda have thought.Otoh the PIPT is in free fall...

Oh,a warning on the bis-fluoroethyltryptamine,EN21 told me the ultratoxic Fluoroacetic acid is likely to be a metabolite-this now makes sense as a series of Fluoroethylamides in an old anti-obesity project mysteriously killed several rats after a very long "incubation" period.Fluoroethylamines are a no go.

But why not Trifluoroethyl-amines?Or 1-Fluoroethyl to mimic DIPT?I have yet to see Another auditory psychedelic.

[morninggloryseed]

What do you mean PIPT is in free fall?

[Vanadium]

Oh,a warning on the bis-fluoroethyltryptamine,EN21 told me the ultratoxic Fluoroacetic acid is likely to be a metabolite-this now makes sense as a series of Fluoroethylamides in an old anti-obesity project mysteriously killed several rats after a very long "incubation" period.Fluoroethylamines are a no go.


thanx for info.

Ok I've seen a "T+" on fluoroacetic acid (merck security sheet) but what about di- or tri-fluoroethyl amines or floropropylamines ? fluro coumpounds are interessant on 2C-T's why not in trypts ?

[iom]

I second the suggestion for MEM. I'm actually rather surprised that this one hasn't received more attention already.

I also would be interested in the other alpha-ethyl phenethylamines as suggested by some others. Sasha and others report ARIADNE, essentially alpha-ethyl-2C-D, to be an anti-depressant at < 25mg. Knowing that 2C-D is not a potent psychedelic compared with 2C-E or 2C-I, for example, other alpha-ethyl-2C-X might produce an interesting blend of psychedelic and mood brightening effects. Who knows?

[Helios.]

iom,
I like your train of thought.
Allow me to extend it.

ARIADNE is probably, like MBDB etc, a dead end.
DOM has a terrible reputation based on actual street events.
DOET on the other hand has a great one.

If anyone wants to do the math, they can.

[Helios.]

bk-DOET.

Edit: They keep moving the goalpost. Haha.

[fastandbulbous]

thanx for info.

Ok I've seen a "T+" on fluoroacetic acid (merck security sheet) but what about di- or tri-fluoroethyl amines or floropropylamines ? fluro coumpounds are interessant on 2C-T's why not in trypts ?

Fluoroacetic acid is incredibly toxic (it's an S1 poison in the UK - in the samw class as cyanides, arsenic salts etc) as it inhibits part of the Krebs cycle (aka citric acid cycle) which is essential in converting glucose into energy (ie ATP) - in fact it's licenced as a rodenticide in some countries labelled as '1080' as I recall.

If the fluoroethyl group is on a nitrogen it is metabolically cleaved to free up the 2-fluoroethyl group which inevitably ends up as 2-fluoroacetic acid; with 2C-T-21 it is directly attached to the benzene ring and isn't subject to separation from the rest of the drug molecule (so no fluoroacetic acid production). As far as I'm aware, trifluoroactic acid is a pretty nasty compound as well - it might not be as potent in inhibiting the Krebs cycle but is used in labs to denature proteins in low concentrations - not something I'd want floating around in my blood

[Dondante]

Apparently Helios already telepathically communicated with the aE-PEAs and said they were a no go.

I still think they are worth a shot. aE-DOM probably has some psychedelic effects unlike the tryptamine example, AET, which is pretty much just a serotonin releaser.

I would love to see some analogues of mescaline (not 2C-x or DOX). I think keeping the 3,4,5 pattern seems interesting despite the loss in potency. TM, TE, or Escaline are in need of further study.

[iom]

Dondante, when you say aE-DOM do you mean ARIADNE from Pihkal? Or do you mean something with an a-ethyl and an a-methyl? ARIADNE or aE-2CD is already described as an antidepressant. My thought is that the aE-2CB, aE-2CI, and aE-2CE might be more potent as psychedelics than aE-2CD and therefore interesting. Although this could just as well be a dead-end.

Has Helios at least verified the "anti-depressant" properties of ARIADNE?

There's probably a long list of 2,4,6 compounds that have yet to be experimented with too. I kind of see two approaches thought on this thread:

1. Which chemicals in the literature (Shulgin, Nicols, etc.) appear worthy of additional attention? Stuff like MEM and the Mescaline analogs fall into this catagory.

2. What kinds of novel and untested compounds appear worthy of synthesis and exploration?

So far most of what has appeared "on the scene", at least as far as psychedelics are concerned has been in category #1. This work has certainly been insightful in that many find compounds like 2C-C, DOC, 4-HO-MIPT to be quite therapeutically valuable.

As far as category #2 is concerned, this is an area that is likely to involve more effort with fewer "rewards". For each new possibility, someone has to devise a synthesis which can often involve multiple instances of trial and error. This person needs a reasonably extensive knowledge of chemistry and access to analytical equipment to verify the identity and purity of the product. Then of course, the chemical must be assayed for activity, possibly by an animal first and then by a human. This is a hit or miss thing. Most of the suggestions in this thread including my own will probably be inactive.

This actually leads me to greater question about our roles as researchers. The primary goal of this board is to be a harm reduction forum. Clearly, there's much more going on here than that and I've noticed there are some very educated people who are participating. Perhaps I should collect my thoughts and share them in greater detail in a new thread.

[Dondante]

Thanks for pointing that out. I didn't realize that ARIADNE is the compound I am referring to. I just called it aE-DOM, because that is what it is referred to as in this paper:

http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=pubmed&cmd=Retrieve&dopt=AbstractPlus&list_uids=7903460&query_hl=7&itool=pubmed_docsum

aE-2C-D would be more appropriate. And I suppose it does not look too interesting as a psychedelic. Perhaps it has merit as an antidepressant. Have any alpha,alpha-dimethyl phens been put under the microscope yet? Here's for tryptamines:


From Tihkal

The alpha,alpha-dimethyl tryptamine homologue (a,a-DMT) is also known. It represents the phentermine to amphetamine relationship where, again there is a three fold drop in potency. It would be a fair hypothesis to expect either of these "DMT's" to be active stimulants at reasonable dosages, but neither have been explored in man.

Along with the 3,4,5 substitution mentioned above, DESOXY is also worth another look.

[nuke]

Yeah, there's not much use looking into AE-PEAs for psychedelic activity, the extra carbon seems to make it too aplanar to be effective at 5HT2 binding sites. They may have some effect of DA/NE is you take them high enough (and maybe other unknown places).

I've been saying someone should make up a big batch of desoxy for a while now.

[iom]

Hmm, now that you mention it... PIHKAL #18 (4-bromo-3,5-dimethoxyamphetamine) looks interesting for the sake of novelty. It's active at 4-10mg, but acts seemingly as an analgesic. There's no reason to expect anything more interesting with the phenethylamine is there? How about CPM, #37? It's about 5X the potency of Mescaline and even longer in action. Might Desoxy-Escaline be interesting?

[morninggloryseed]

I think I already suggested this...but fluoromescaline! More specifically....4-trifluoromethoxy-3,5-dimethoxyphenethylamine. What is appealing here is that the mescaline structure is left intact. And as with other trifluoro analogues...if we see a 10X increase in potency I think this would be attractive from all angles. Let's face it, potency is a big factor in being brought to market. The days of 2C-N, 2C-G, 2C-D are over. :(

[nuke]

4-trifluoromethoxy-3,5-dimethoxyphenethylamine

No go I think, o-demethylation will cause problems when the fluoromethyl group gets bumped off and gets to cause havoc on its own. 4-trifluoromethylthio-3,5-dimethoxyphenethylamine and 4-trifluoromethyl-3,5-dimethoxyphenethylamine should be fine, though.

[morninggloryseed]

But I thought mescaline was deactivated by way of the chain...not the 4-position. Principal metabolite is 3,4,5-trimethoxyphenylacetic acid so the 4-position stays intact in the momma molecule.

[nuke]

Deamination is the foremost method of metabolism, but after that you get n-acetyl-3,4-dimeo-5-ho-mescaline, then n-acetyl mescaline... there are a bunch of other urinary metabolites too in very small number, and I'm willing to bet one of them has a 4-hydroxy group, but then, how much do you need of trifluoromethanol/trifluoroformic acid to cause problems in your body/brain? I don't know, but it wouldn't be foremost on my tasting list because of that, probably something for rats to try first.

edit:
pretty sure this paper specifies a 3,4,5-trihydroxy metabolite, but I can't find a full text anywhere online:
METHYLATION AND DEMETHYLATION IN RELATION TO THE IN VITRO METABOLISM OF MESCALINE
John Daly, Julius Axelrod and Bernhard Witkop

[Helios.]

Dondante,
That's your egg.
:p

[hugo24]

I guess the Trifluoromethoxi would be stable metabolically,but a kill in activity could be an issue (just a feeling from a few other though unrelated compounds).But as nuke said,the trifluorodesoxy should be good stuff.

Is the reason nobody produced Desoxy the "spiritual crisis" chapter in PIHKAL??

[morninggloryseed]

That, or the compound just doesn't appear interesting. It doesn't seem a winner in PIHKAL, but then neither did 2C-D. I really think with desoxy that the absence of activity may be a function of dosage. I think Shulgin says up to 100mg or 125mg?

Take it up to mescaline-like dosages and it could shine...but something active at >250mg is not marketable I think.

[Dondante]

I'm not sure if I completely understand what you mean by not marketable. I mean the precursors for these compounds are extremely cheap, correct? If they really are super cheap, then it's just the labor (not sure how hard it is to make big batches), and then the cost of marketing (should be practically nothing). So basically it would be more a function of how much they could sell, and not necessarily how potent the compound is.

I understand that compounds that are active at the 1-5 mg might be slightly more profitable, but since there are so many of them on the market I think introducing a new interesting compound active around 100-250 mg could also be profitable because of it's uniqueness and high desirability. It would have to be a damn good compound. Maybe I'm underestimating the cost of precursors and labor. Someone want to fill me in here?

[morninggloryseed]

Well that is very true, but if there is only two dosages in a gram....the seller would either be forced to sell a gram for less than $10...or there would be very few customers. Most people are not going to pay $50/g if they only get one or two dosages. So profit is cut dramatically. Why would one want to go to such trouble?

[hugo24]

At least you're not going to lose 20 doses sticking on the baggie ...

And if you're throwing in the safety argument,100-200mg appears like an ideal dose.Not only because of those licking said amount from the baggie...

I'm tempted to bring in 2C-T again,nothing but glowing experiences from 80-130mg in "Psychedelische Chemie" (6 reports).Of course there are few downsides,mainly a somewhat too short duration.Otoh MAOI properties could be on the safer side.

[Dondante]

If it was 5 doses/gram, I'd pay $50 depending on the substance. MDMA seems to be doing just fine and it's not super potent. Same with methylone and it sucks. It would take a gem, but I don't think dosage should be prohibitive. If you're talking about 300-500 mg, then perhaps it should, but 50-250 mg is doable on a large scale in my opinion.

[morninggloryseed]

I'm tempted to bring in 2C-T again,nothing but glowing experiences from 80-130mg in "Psychedelische Chemie" (6 reports).Of course there are few downsides,mainly a somewhat too short duration.Otoh MAOI properties could be on the safer side.

If "being 2C-T in" means I get some....please do! I just know this one is a gem of gems. All reports I have read (mostly a few private ones not published) seem to hint what you are saying...this one is a keeper. I envision a trip very much like 2C-D...but with added warmth and empathy that the 2C-Ts seem to produce. I would so much love to see this one come to market.

Also Hugo, what is "Psychedelic Chemie" and where can I read these reports?

As for desoxy...I'm not saying anything other than its activity is still pretty much undetermined and that (plus the high dosages) is probably why it is not marketable. I mean by golly, I'd love to know more about it...and I like it just because (if anything) it is a positional isomer of 2C-D...and positional isomers of the 2Cs fascinate me. But from what I know about the market these days, we are unlikely to see it for those reasons. But if there are anymore places like the now defunct sneezy-sounding place that did bring new things to market (PMEA, M1, 3C-P, etc) of low potency or unknown potency, please being em on!

[nuke]

http://www.sjamaan.com/de/0237_Psychedelische_Chemie_(Daniel_Trachsel___Nico las_Richard).html

^^ you can buy the psychedelische chemie there, it's a german index of a number of psychedelic drugs. I'm not sure if there are any copies floating around online.

As an alternative to desoxy, fluoroethyl or fluoroform in the 4 position might improve the potency 2-5x.

[Vanadium]

. As far as I'm aware, trifluoroactic acid is a pretty nasty compound as well - it might not be as potent in inhibiting the Krebs cycle but is used in labs to denature proteins in low concentrations - not something I'd want floating around in my blood

yes, ok , TFAA is a highly corrosive acid ( the electronegativity of fluoro-atoms hold the dots back: very acid !) but isnt really "toxic" for the organisme not as fluoroacetic.

If you take 10 mg of e.g. 5-methoxy-N,N-bis(2,2,2-trifluoroethyl)tryptamine [M(5-MeO-BTFET) = 354.3 g/mol]. so, 10 mg = 0.028 mmol. when this compound is detroyed , like you said : 0.056 mmol of TFAA is produced (6.44 mg of this).
Is 6 mg of TFAA clearly harmful for the organisme ?

__________________________________________________ ____-

Why not more explore the FLY's and DragonFly's molecules ?
i've read the DOx thread and favorite DOx compound is definitly DOC . what about a DOC-Fly/DFly ? or DOM-Fly/DFly ? or 2c-E, 2c-I, 2c-T-2, 2c-T-7, ... with cyclic/aromatic ethers ?


Oops sorry for my fucking english ...

[hugo24]

MGS,its a bit like the Swiss PIHKAL...again we are also waiting for the follow up.The guy IMHO is 2nd to Sasha in creating new compounds,all the fluorinated compounds,the thios,Mescaline analogs (you might remember the Helvetica Acta articles).

nuke-I'm done with fluoroethyls (maybe except DOEF) generally,see my 2C-EF account here.The reduced potency in the 3,4,5 series just doesen't bode well.I can imagine a whatever alpha-fluoroketonmetabolite might excert some toxicity ala fluoroacetic acid.The higher homologues of the fluoro fatty acids are also toxic (though only the "mean" C homologues)!

On the fly's,since they have a much increased duration,it cuts the selection mainly to 2C-D,2C-T,maybe 2C-T-2 and DOM fly just for historical reasons.

[nuke]

Swiss? Shows how much I've read of it, I'd just heard of it before a bunch of times. :P God, I'm miss information in this thread.

>>Hugo
I didn't know you assayed 2c-ef but I guess it must not be too glowing.