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Thread: Benzofuran analogues of Tryptamines (e.g. 5-MeO-BFE)

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    Benzofuran analogues of Tryptamines (e.g. 5-MeO-BFE) 
    #1
    Bluelighter foolsgold's Avatar
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    anyone heard of this stuff its getting sold by one vendor [snip] iupac [2-(5-methoxy-1-benzofuran-3-yl)ethyl]dimethylamine
    Last edited by sekio; 07-10-2011 at 00:53.
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    #2
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    Please do not post (even speculative) vendor details. we don't need to know "brand names" or supply status.

    Dimemebfe (what a mouthful) is the benzofuranyl analog of 5-MeO-DMT with the indole nitrogen replaced with an oxygen. It's a psychedelic tryptamine, basically, though wiki says it's a little less potent than 5-MeO-DMT.

    It should form salts and freebases just like MeODMT, and dosing is probably similar (few milligrams to 10s of milligrams, smoked/snorted/eaten).

    This thread really belongs in Psychedelic Drugs.
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    #3
    Bluelighter foolsgold's Avatar
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    sorry n thanks sounds interesting may have to get some saturday
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    #4
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    It sounds retarded, the dimeme is redundant (edit: oh no its not but come on...) and part of it is acronymous while another part is not. I say call it dimethyl-B.F.E. then, which is derived the same way from the formula.

    I've seen the question pass around once or twice what would happen if you would play around with heteroatoms / cycloether bonds or whatever you should call them. I mean sulfur in the methylenedioxy and stuff like that, and indeed also substitutions in tryptamines.

    When I first read the post that said its a benzofuranyl analogue I immediately imagined an extra [6,7]-ring. I guess we dodged a 5-MeO-DMT halodragonfly there hehe, though in reality it would probably be very inactive.

    Well new info is welcome on this chem!

    3 - 6 times lower affinity to rat 5-HT2A, 2 times lower to rat 5-HT1A receptor

    #16 J. Med. Chem. 35 2061 1992 - Benzofuran Bioisosteres of Hallucinogenic Tryptamines

    Zbigniew Tomaszewski, Michael P. Johnson, Xuemei Huang, and David E. Nichols*
    Last edited by Solipsis; 07-10-2011 at 03:34.
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    #5
    That's where you'd be wrong actually, they are active (benzofuranyl tryptamines). More details when I'm at home with my article stash...
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    Bluelighter Fagott's Avatar
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    Quote Originally Posted by MattPsy View Post
    That's where you'd be wrong actually, they are active (benzofuranyl tryptamines). More details when I'm at home with my article stash...
    Uh VERY interesting.....
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    #7
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    from another forum:

    This is certainly a potentially interesting one. By substituting the indole for a benzofuran ring system this compound seems a pretty close structural approximation to 5-MeO-DMT, and yet is uncontrolled in the UK (which I'd assume is the primary target market). It'd also be uncontrolled in the US, though may be deemed analogous to the controlled 5-MeO-DMT under the Federal Analog Act or various state laws under certain circumstances.



    Will it work though? The indole nitrogen moiety plays an important role in the interaction between tryptamines (be it DMT or substituted tryptamines like psilocin and 5-MeO-DMT) and the serotonergic receptor proteins. Hydrogen bonding between the nitrogen and residues in the protein stabilize and co-ordinate the docking of the drug ligand into the binding pocket in a way that will result in the signal being transduced, resulting in serotonergic activity.

    Can the oxygen moiety of the benzofuran suitably fulfill this role? Oxygen residues are certainly also capable of hydrogen bonding, though if I recall correctly they tend to form weaker interactions than those of nitrogen. The precise co-ordination of the interaction may also differ slightly between the two since the nitrogen moiety has an associated proton whereas the oxygen does not. This may account for the reportedly high active dose when compared to its tryptamine counterpart. It certainly seems plausible that it would have some psychoactive properties though, even if it is not as pronounced as that of the tryptamine.

    Then again determining the precise relationship between drug structure and activity is difficult. One just needs to look at the reported differences in experience between methamphetamine and "methiopropamine" to see that two structurally analogous substances that differ only by substitution of the ring system will not necessarily give similar results. That said I think this compound is a better approximation to 5-MeO-DMT than "methiopropamine" is to methamphetamine, so I'll be watching this one with some interest.

    I guess the biggest looming question will be that of safety. Benzofuranamines are pretty new chemical territory, so whether this substance is metabolically safe over the short and long-term is unestablished. It might prove to be just as safe as the tryptamines or it might give everyone toenail cancer 10 years from now. As with most drugs (e.g. MDMA, cocaine, many pharmaceuticals) it seems probable that there will be a very small but unpredictable subset of the population that will suffer serious idiosyncratic adverse drug reactions to substituted benzofuran drugs.

    Another concern might be that the alterations to the ring system chemistry may favor interactions with serotonin receptor subtypes other than those typically sought for recreational effect (usually 5-HT2), which could lead to unwanted and potentially dangerous side-effects such as overheating. In any case it should certainly not be assumed that this would be a like-for-like substitute for 5-MeO-DMT. The relationship between dose, effects, side-effects and toxicity may be quite different. As always with novel substances, caution is advised.

    It's certainly nice to see some development of the tryptamine family seeing as it has been somewhat neglected in recent years.. even if that development is a substance that is technically no longer a tryptamine at all!
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    #8
    By benzofuranyl tryptamines I did not mean a ring swap of the indole system with that of a benzofuran. I meant along the lines of what Solopsis mentioned, a cyclization of the O at -5 back to either -4 or -6 as a furan (5 membered) or bigger (6 membered) system.
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    #9
    Bluelighter ungelesene_bettlek's Avatar
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    generally, I am of the strong opinion that when another online source is quoted, the corresponding link should be given. this would make live so much easier for us all. now I had to waste some unnerving minutes to google them myself, but now I can at least save this tedious work for others:

    Quote Originally Posted by sekio View Post
    wiki says it's a little less potent than 5-MeO-DMT.
    http://en.wikipedia.org/wiki/Dimemebfe

    Quote Originally Posted by Fagott View Post
    from another forum:
    http://www.drugs-forum.com/forum/sho...d.php?t=168921
    Last edited by ungelesene_bettlek; 07-10-2011 at 12:58.
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    #10
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    Quote Originally Posted by ungelesene_bettlek View Post
    generally, I am of the strong opinion that when another online source is quoted, the corresponding link should be given.
    I agree, I was just unsure if it was maybe ill seen to link to another forum......
    But I see know that linking to drugs-forum.com would be fine of cause. itīs just forums with vendor discussions and such that shouldnīt be linked.
    Last edited by Fagott; 07-10-2011 at 17:25.
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    #11
    Bluelighter Fagott's Avatar
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    I donīt believe this chemical is available anyway. Still itīs interesting to discus.
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    #12
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    Quote Originally Posted by foolsgold View Post
    its ment to be out now on one site
    No, so I do not think it is, my young padawan. My message inside a message you do not understand.
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    #13
    Bluelighter foolsgold's Avatar
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    just got up thats why lol
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    #14
    Bluelighter ungelesene_bettlek's Avatar
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    Quote Originally Posted by foolsgold View Post
    just got up thats why lol
    you obviously still don't understand the message in the message, even after being bumped on it.
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    #15
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    I wonder if the larger post quoted was written by someone who read the Nichols article. Of course in that it is said that it is about 1/6th as potent in terms of sheer receptor affinity but that is not a guarantee for a psychedelic.
    If hypothetically for a second we would just plain assume it was, you would expect more side-effects from this because the 5HT1A receptor is involved in heart-rate, nausea, anxiety, respiration and cardiovascular function to name a few that are not affected by 5-MeO-DMT in a very positive way... and dimethyl-B.F.E. relatively has more affinity for 5-HT1A even if 5-HT2A (responsible for psychedelia) is still more selectively targeted. So the proportion is different and if you read that very simply it does not bode well.
    Combined with the lower potency it doesn't seem too exciting. I do think that a somewhat less overwhelming form of 5-MeO-DMT could be more worthwhile and accessible but 5-MeO-MET would probably be a better bet.
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    #16
    Quote Originally Posted by MattPsy View Post
    That's where you'd be wrong actually, they are active (benzofuranyl tryptamines). More details when I'm at home with my article stash...
    I'm really interested in what you're talking about. Any chance you could post the titles of any articles describing these benzofuranyl analogues?
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    #17
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    Are they even called benzofuranyls? A benzofuranyl indicates two rings namely the phenyl (benzo) and furan. With dimethyl-B.F.E. the furan ring replaces the pyrrole ring of the indole/tryptamine. But with the 6,7-furanyl analogue of the tryptamines I suggested there are three rings: the intact tryptamine with its two rings (phenyl and pyrrole) and an extra furanyl going from the 6 and 7 position. Alternatively you could say it is a benzofuran with an extra pyrrole either way the result is 3 rings.

    So Matt some extra clarification there would be helpful because the nomenclature is incorrect or incomplete with what you are implying. I could not find anything glancing over the Nichols articles I have.

    If we keep going back and forth about this it may call for splitting this thread.
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    #18
    has anyone got any more info on this chem?
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    #19
    i have some of this,its like orangey gooey stuff,need some advice,how do you consume it?,vaporize it?,swallow it orally?,please can anyone give me some decent info on how to properly consume this material?.
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    #20
    Quote Originally Posted by flameboyd2012 View Post
    i have some of this,its like orangey gooey stuff,need some advice,how do you consume it?,vaporize it?,swallow it orally?,please can anyone give me some decent info on how to properly consume this material?.
    Even if that is genuinely dimemebfe, we can't really tell you much about the dosage, roa, etc. That's why they call it a "research chemical," because when you take it you're the one doing the research. But do you really want to be some random, sketchy vendor's guinea pig?
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    #21
    Bluelighter ungelesene_bettlek's Avatar
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    Quote Originally Posted by flameboyd2012 View Post
    i will be honest is from a fairly trusted source,spoke to him on the phone but legally he cant tell me how to consume it,he is selling it from his website(obviously i cant say which site),but i believe its the real deal and i dont mind trying out a very small amount to begin with to see how it goes
    have you looked up your "trusted vendor" at *site name edited out* ? if not, I would do so.
    Last edited by Solipsis; 21-10-2011 at 19:21.
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    #22
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    Quote Originally Posted by Indole View Post
    Even if that is genuinely dimemebfe, we can't really tell you much about the dosage, roa, etc. That's why they call it a "research chemical," because when you take it you're the one doing the research. But do you really want to be some random, sketchy vendor's guinea pig?
    This. Have you read through the thread at all?

    Be extremely careful when dosing with unknown chemicals.

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    #23
    i recently got a free sample, i believe the site was marketing it under the pseudonym "No vendor discussion por favor"

    has anyone tried it yet?
    Last edited by Solipsis; 21-10-2011 at 23:20.
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    #24
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    Quote Originally Posted by deuterium View Post
    i recently got a free sample, i believe the site was marketing it under the pseudonym [...]

    has anyone tried it yet?
    Dude. Are you serious. That vendor looks sooooo sketchy. I have vendors in spades man. Believe me, weird orange goo from that place is not a good idea. Please. Just don't.
    Last edited by Solipsis; 21-10-2011 at 23:21.
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    #25
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    No, nobody has tried this compound, due to a lack of any sort of proper pure reference material.

    As a wild guess, acitivity is probably at the 1-2mg level when smoked or taken parenteral. I would not attempt oral administration of this.
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