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Phenethylamines The Big & Dandy Bromo-Dragonfly/DOB-Dragonfly Thread

I don't think the MD-(methyl)-aminorex derivative will be worthwhile. It has been made in the original study of aminorex. They only tested it as an anorectic; potency dropped 25-fold compared to aminorex. That doesn't bode well for any useful activity.
 
Found this, supposedly from one of the next big shulgin books,

From the working draft of an upcoming book by Shulgin, "Psychedelic Index", Transform Press, 2004

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Names:

2C-B-FLY
1-(8-Bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane

Registry Numbers:

CARN
HCL salt 178557-21-6

Natural sources:

Not known in nature

Synthesis:

From hydroquinone (with 1-chloro-2-bromoethane) to 1,4-bis(2-chloroethoxy)benzene (with Br2) to 1,2-bis(2-chloroethoxy)-2,5-dibromobenzene (with BuLi) to 2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran (with dichloromethyl methyl ether) to 4-formyl-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran (with CH3NO2) to 4-(2-nitro-1-ethylene)-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran (with LAH) to 1-(2,3,6,7-Tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminoethane (with Br2) to 2C-B-FLY (Monte, et al., 1996).

History:

The "FLY" name was inspired by the two dihydrofuran rings that extend oppositely from the sides of the benzene ring. When they are aromatized (furan rings) they are planar with the benzene ring and the code name is "DRAGONFLY" and they are listed as DFLY derivatives.

Physical properties:

C12 H14 Br N O2
HCl salt m.p. >310 (EtOH, EtOAc) (Monte, et al. 1996).

Pharmacology:

The five "FLY" compounds (2C-FLY, 2C-B-FLY, FLY, B-FLY and DOM-FLY) were assayed in a drug discrimination paradigm with LSD-trained rats, and in interactions with various serotonin receptors. (Monte, et al., 1996).
2C-B-FLY is active in man at an oral dose of 10 milligrams (Shulgin, 2003a)

Legal Status:

2C-B-FLY is not listed in any law.
 

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as the "flies" are at heart "benzopyrans
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No, pyrans are six membered oxygen heterocyclics (5 carbons & an oxygen. THC has a pyran ring at its heart), the flies/dragonflies are benzodifurans (5 membered oxygen heterocyclics). If you look at it in a certain way, it can be seen how one of the furan rings is a direct replacement for the pyrrole part of indole (both oxygen and nitrogen have the lone pairs required for receptor binding), the oxygen replacing the nitrogen.

I don't think that they'd be teratogenic (but that's just an educated guess), but they may act as intercalators and slow translation of DNA to mRNA, but then again, there are plenty of drugs that do that (eg some phenothiazines etc); nowt too serious as long as you don't have an impaired immune system


f&b, what is this 2c-b/bzp hybrid you talk of?
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It's BZP, but with the benzene ring carrying the same substitution pattern as 2C-B/DOB (compound is 1-(4-bromo-2,5-dimethoxybenzyl)piperazine dihydrochloride. From what I've heard, it's worth its weight in shit! ie not too good to say the least. NZ has some of the strictest, non analogue act type drug laws going with respect to psychedelics. 2C-B is def. covered by them
 
alright.. i'll bite... what does 2C-B-FLY have to do with Bromo-Dragonfly? it's not like if you find 2C-B-FLY, you can roll to your lab real quick and make it into the fully aromatic dragonfly... so then, why not a thread for 2C-B-FLY?
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As discussed earlier, FnB's figure is in error - the molecule (b) is bromo-fly, or B-Fly. Molecule (c) is B-DFly (bromo-dragonfly).

2C-B-Fly would be the same as B-Fly, but without the methyl on the alpha carbon - the same is the difference between 2C-B and DOB.
 
Yep the label attached to b) is incorrect, it should read bromo-fly. This was before I discovered that the non-aromatic compound was the 'fly' and the aromatic compound was the 'dragonfly'. The factual data regarding receptor binding was correct, just got the nomenclature wrong
 
Wasn't the non-aromatic series called the butterflies at some point in time?
 
Anyone else tried Br-DFLY out yet???

Does anyone know what the stability of this compound is like, for long-term storage?
 
Ghettotastic_bong said:
^

Yes, and i wrote briefly about it on an earlier page.
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Thats why I said anyone else .

Sorry, ghettotastic, but I remain a little dubious about any blotter allegedy soaked in B-DFLY - no matter how confident you are of the source. I guess I'm not going to be totally satisfied until someone does a proper GC/MS workup, but for now, reputable vendors will do - ie not those slinging blotter.

Perhaps you could tell us the dosage that was put on the blotter you received?
 
Neo1 said:
Does anyone know what the stability of this compound is like, for long-term storage?
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There's every reason to believe that it's long-term stable under the usual, proper conditions: room temperature, protected from light and moisture.
 
This thread would be a lot more useful if people could post their experiences, including duration and effects at a range of dosages.... rather than talking about availability and prices.

... Unless you've seen a particular sheet which is widely distributed and verified as bromo-dragonfly. But it shouldn't be a surprise to anyone that something active around 100ug and offered at more affordable prices might be misrepresented as LSD.

My advice would be to eat only one blotter your first time to see how you react. Even some legitimate LSD is being layed strong enough to overwhelm noobs.

My other hope is that LSD drops in price and increases in availability so that there will be much less motivation for people to lay DOI / DOB / 5-meo-AMT / DOC / Bromo-Dragonfly, etc.

gotta go, peace
 
bluedolphin said:
This thread would be a lot more useful if people could post their experiences, including duration and effects at a range of dosages.... rather than talking about availability and prices.

... Unless you've seen a particular sheet which is widely distributed and verified as bromo-dragonfly. But it shouldn't be a surprise to anyone that something active around 100ug and offered at more affordable prices might be misrepresented as LSD.
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I'm sorry, but we've all endured way too many years of alleged mescaline microdots and 5-meo-amt passed off as LSD to trust drug dealers, widely distributed or not. How would you "verify" a sheet as B-DFLY, rather than say DOx?

Online vendors are probabably marginally more reliable, but I still wouldn't be entirely certain that you'd get what has been represented.

There's every reason to believe that it's long-term stable under the usual, proper conditions: room temperature, protected from light and moisture.
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I know that one source was supplying small quantities of B-DFLY in a solution of 40% ethanol - any ideas how this would effect stability? I remember that some people found that tryptamines like iprocin decayed very quickly in solution...
 
Well, most amphetamines are quite stable. Don't know why this one isn't? On the other hand, my knowledge about chemics is a bit limited.. :)
 
any pea could be turned into a fly compound ?
IF so that would be great to try this with....mmm mescaline (!!), mdma, mda, dom, and a few others....well especially mescaline
IS sucha thing possible ?
 
genaro: you really cant turn everything into a fly/dragonfly because of the spots on the benzene ring that must be occupied to make it a fly/dfly. as of right now, the only compounds that could be made such are the 2c- (including 2ct-) and do- (including aleph-) compounds, excluding the 2cg and ganesha (g-x) series, although 2cg and ganesha (g-x) series could be made into hemiflies/hemidragonflies. maybe it'd be possible to have mdxa hemiflies/hemidragonflies too...
 
genaro: you really cant turn everything into a fly/dragonfly because of the spots on the benzene ring that must be occupied to make it a fly/dfly
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In order to be a suitable candidate for a dragonfly analogue, the molecule MUST contain a 2,5-dimethoxy ring substitution pattern. As the formation of the benzodifuran structure also occupies the 3 & 6 positions (the other end of the furan ring's attachment to the benzene ring), that only leaves the 4 position for altering the ring substituent.

As tathra has pointed out, this means that there is no possible dragonfly analogue for any compound other than those carring the 2,4,5-trisubstituted ring - any further substitution means that only a hemi-dragonfly is possible, and then only if there are methoxy groups on the 2 & 5 position

For example - it would be possible to produce a hemi dragonfly of DMMDA (2,5-dimethoxy-3,4-methylenedioxyamphetamine), but not of DMMDA-2 (2,3-dimethoxy-4,5-methylenedioxyamphetamine)
 
^^^

So what about 3,4,5- substituted PEAs - Genareo mentions mescaline. If the furan rings were closed up in the same way, then you'd have a structure like the DFLY, but with both oxygens on the "wings" pointing in the same direction... ie towards the methoxy group in mescaline.

Or the otherway around, starting from TMA-6 - giving the furan rings withe the oxygens pointing back towards the amine...

These two wouldnt be dragonflies.. quick think of a snappy new name! :\
 
Is Shulgin really putting Bromo Dragonfly in his new book? That would be awesome! 8o

Edit: I found synthesis instructions on another board. Obviously actually making brdf does not concern my enquiry - I was interested purely for the purpose of academic conjecture.
 
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I think a very good compound would be 2C-D-DF if it shares the properties of 2C-D on a higher level. It can't be made by Nichols' method and afaik hasn't been made yet.
 
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