• Psychedelic Drugs Welcome Guest
    View threads about
    Posting RulesBluelight Rules
    PD's Best Threads Index
    Social ThreadSupport Bluelight
    Psychedelic Beginner's FAQ

DOCN (2,5-dimethoxy-4-cyanoamphetamine)

clubberdude

clubberdude

Bluelighter
Joined
Feb 26, 2011
Messages
563
In my late Sunday night research, and because I have a fascination with the DOx class of chemicals, I came across DOCN (2,5-dimethoxy-4-cyanoamphetamine)

Scroll down to analogue #41.

http://isomerdesign.com/PiHKAL/explore.php?domain=pk&id=64&name=DOC#

Sounds insanely toxic to me. Has anyone else come across any studies of this compound? Is there any history of it ever being synthesised? (asides from theoretically/on paper of course). Has it ever been assayed in humans? Would anyone like to hazard a guess at whether it is psychoactive in humans? And at what probable dose? Looks like a fascinating compound, but toxic as well. I'm left wondering what the therapeutic ratio might be for this chemical.

Any more information on this compound would be fantastic.
 
clubberdude said:
Sounds insanely toxic to me. Has anyone else come across any studies of this compound? Is there any history of it ever being synthesised?
Click to expand...

Why do you say it sounds toxic? The presence of a cyano group doesn't guarantee toxicity, in fact in this case when its attached to the 4 position of the aromatic moiety it acts a pseudohalogen, engendering effects that are probably somewhat similar to the 4-halo dimethoxyamphetamines (essentially any non-bulky hydrophobic group on the 4 position will yield effects similar to the 4-halo DOx compounds because it maximizes interaction between the compound and the hydrophobic region of the receptor, which is one of the primary predictors of psychedelic potency in DOx). I believe the compound was studied and published on by Glennon et al, I can dig up a reference if you're really interested.
 
Last edited:
With regards to that reference, I'd definitely be interested in reading it - the DOx compounds fascinate me. I guess though you are probably right - the cyano bit does sound intimidating, but as you say, when combined with the remainder of the 2,5-dimethoxyamphetamine structure, that may well alter the toxicity profile somewhat.

In a related vein, DON sounds as though its toxic to me as well, I guess the name 2,5-dimethoxy-4-nitroamphetamine just has a toxic ring to it, though again, the toxicity may be way off what I imagine (have very limited experiences with DOx's but have tried DOC and absolutely love it!)
 
check out

Nelson, DL; Lucaites, VL; Wainscott, DB; Glennon, RA. Hallucinogenic drug interactions at human brain 5-HT2 receptors: implications for treating LSD-induced hallucinogenesis. N. S. Arch. Pharmacol., 6 Sep 1998, 359(1), 1–6.

Full text is available for free here
 
I'll check that paper out (assuming my crappy internet dongle allows me of course!) - cheers for that!

EDITED TO ADD: That receptor binding affinity data is fascinating. Answers a number of questions I had about relative affinities of the DOx compounds have to the different 5HT subgroups. Interestingly, DOCN and DON both had relatively low binding affinities (surprisingly low in the case of DON, given it is supposed to be rather psychedelic apparently - from the limited number of experiences I've read), whereas DOI, DOC and DOB had higher binding affinities (though this would be perhaps expected given they are well established and popular psychedelics).
 
Last edited:
DON's low binding affinity was confirmed with teh few reports found on this site--- i believe the average dose was in the 50+ milligram range, much less potent by weight than every other DOx and nearly every 2C-x.
 
Greenmeanies.. I believe the active dose for DON is nowhere near 50mg. Wasn't this chemical distributed on blotters in Russia?
 
^ Correct, I think a solid dose of 2C-N would be about 150 mg - I don't think I know of another 2C-X that is less potent, not counting things like 2C-H. I've wondered if 2C-X body load is at least partially dependent on the total amount needed in a dose... It would explain why 2C-N is reported to have such a strong body load. Though mescaline is an exception or disproves this, since it does not have an insanely strong body load... considering it has peculiar pharmacology it can very well be an exception. I haven't yet dared to try my 2C-N, it will probably be one of the last ones that is up.

Anyway about DOCN: I see that 2C-CN can be made from 2C-B, though I assume it is also possible from 2C-I with the better leaving group (iodo)... so it's probable DOCN can be prepared from something like DOB or DOI. The assumed toxicity mentioned is actually ambiguous: In (pure) DOCN, there is no real cyanide present since cyanide technically refers to the ionic compound CN- (minus for negative charge). The cyano group in DOCN is not bonded to the molecule ionically, but instead with a covalent bond. The difference is: ionic compounds can be paradoxically very stable (against heat...) when joined as a salt - like potassium and cyanide make potassium cyanide - though when added to water quite a lot of them fall apart to form the positive and negative counterparts. Our bodies are mostly water, so potassium cyanide releases ionic cyanide which is damn toxic as most know. But the covalent bond in DOCN is different: without any water present it can typically withstand less heat without falling apart, but on the other hand if put in water the "CN" group is held together more or less as tightly as the rest of the molecule is held together. So practically no cyanide.
Enzymes in your body can chop off a lot of different groups off of chemical compounds, but if CN was one of them we would not be here today.

I said the toxicity is ambiguous, I meant that while DOCN itself might not be toxic (in terms of cyanide poisoning), a sloppy synthesis may still contain cyanide since it is an ingredient to make it... so to speak. So even if ordered it is probably smart to do like 2 or 3 types of indicator tests on it to see if the cyanide is quenched (destroyed) properly during the procedure.

Hmm yea I used to be more easily excited by the idea of such compounds, and to discuss them. But I tend to get these 'realist' feelings now that talk is cheap and similar to children's fantasies (also in the sense that there is just not enough known about the topic to stay very factual about it). I don't mean to be condescending or a buzzkill, but truth be told I am most interested in that rare report on it that may exist instead of discussing things like: say there would be multiple cyano substitutions... wouldn't that be something?

:)
 
I looked at that pdf and DOCN is only weak interaction with the receptor but remember that Lexapro also CN in the aromatic nucleus so not necessarily insanely toxic.

DOHx it said is higher potency than DOB and DOI and was strongest binding interaction in the table. Why then have I never heard of it before?

Has anyone ever tried it? how potent is it? Nothing on wiki either.
 
Smyth2 said:
I looked at that pdf and DOCN is only weak interaction with the receptor but remember that Lexapro also CN in the aromatic nucleus so not necessarily insanely toxic.

DOHx it said is higher potency than DOB and DOI and was strongest binding interaction in the table. Why then have I never heard of it before?

Has anyone ever tried it? how potent is it? Nothing on wiki either.
Click to expand...

https://www.erowid.org/library/books_online/pihkal/pihkal061.shtml

The preparation of DOAM was, as a matter of fact, the last of the homologous series of compounds actually completed, which stemmed from the original discovery of DOM. The "Ten Classic Ladies" concept was mentioned under ARIADNE, and the adding of a methyl group in the place of a hydrogen atom at the 4-position-methyl led to the synthesis of Ms. HECATE and gave rise to DOET. The whole series of methyl-ethyl-propyl-butyl-amyl compounds was appealing to me, in that the potency seemed to increase initially as the chain got longer, and then it abruptly dropped off. Wouldn't it be nice, I thought, if I could interest some pharmacologist in looking at this tight set of drugs with some animal model, to see if there is some neurotransmitter activity that would show a parallel action.
Click to expand...

DOAM comes right before the hex

Low Ki does not say everything?

If you wonder about possible qualitative effects of DOAM at higher doses, not trusting Shulgin's unwillingness to proceed, this might put you off:
https://www.erowid.org/library/books_online/pihkal/pihkal063.shtml

Also...2C-iP and DOiP were not exactly promising, or were they.. after all?

DOPr might be like the sweet spot, but it will also remain a matter of taste. I can imagine not liking the 4-alkyls at all, at least for some people.
 
how come you're fascinated by the DOx series of chemicals? I'm intrigued by them as well, but I don't know anything about pharmacology.

Experientially, the body load of low dose DOM felt very artificial. Kind of like a very mild poison. I liked other aspects of DOM's effects though. I'm tempted to say DOC felt cleaner, but it's hard to compare high dose DOC to low dose DOM. 2C-C and 2C-B are the highest rated halogen phenethylamines so perhaps DOC and DOB are the best amphetamine counterparts.
 
I am also fascinated by the DOX compounds. It's because back in 2006 I encountered DOC for the first time and I fell in love with the effects. I find it to be just about the perfect psychedelic for many purposes, the effects are a mixture of profound and euphoric and visual and physical, and it reliably produces one of the greatest states I can think of on the second half of the trip. I've since tried DOI, DOB, DOM, DOET, DOT, and DOPr, and they're all interesting in their own way, though DOC is my favorite still by far. They're just an interesting class of substances. I've got DOiP and DOF to try as well, haven't gotten to those yet. I'd love to add DOAN, DON, and DOEF to my list as well, if I ever get the chance.
 
And which one was the closest to DOC? DOB I bet.

Very impressive, by the way, the number of those you've tried.
 
Hmm, none have that same sort of effect than DOC has. I only tried DOB once, and I was in a period of intense psychedelic tolerance so I didn't get to experience its full effects, I feel. I could imagine probably DOB would be the closest, but people generally report unpleasant bodyload pretty often on DOB. DOC has a bodyload in the form of a lot of energy but I can channel the energy into physical stuff and it just feels good.

DOPr also feels good, in fact even more consistently good than DOC but thus far I have found it to be quite different as well. It's much smoother and less energetic, with a sense of peace instead of the euphoria of DOC.
 
Last edited:
The visuals on doc are definitely nice. Mainly just extreme patterns not much morphing. But that said doc puts me into a state where i cant remember what i was talking about mid sentence. Its like a word is always on the tip of your tounge but you cant get it out. That can be very hard on me especially if i am trying to connect with others. That ave the residual stimulation will leave you up for 2 days. Still have a whole gram but i preffer 4 ho met or lsd better. Great festival drug wool never run out of energy!
 
Yeah I get loads of energy from it too and trouble sleeping for a good 24 hours. It is indeed a great festival drug, one of the very best, it'll cut through any amount of fatigue. I went to a 3-day/night music festival and on the first 2 days/nights I took so many drugs, on the third morning I felt like a zombie, just absolutely wrecked. I took 3.5mg of DOC at around 1pm, after failing to get out of my fog, and the rest of the day was brilliant, probably the best of the 3 days.

My favorite part of DOC is something that not everyone reports, it's the plateau stage, post-peak, where all of a sudden it transforms into this thing where I feel just absolutely godly, confident, coherent, euphoric, energetic, funny, and incredibly peaceful.

I'd love to know how DOCN compares. Are there any reports or is this thing pretty much just theoretical at this point (in terms of effects, not whether it can be synthesized)?
 
^ I think I've heard that -CN is chemically similar in some regards to -X (X=Halogen), so they might share some of the qualities of DOC, DOB; don't quote me on that though, just a guess...
 
You must log in or register to reply here.
Top