• Trip Reports Moderator: M!$ter-ED

5-(2-aminopropyl)-2,3-dihydrobenzofuran hydrochloride - first trial of a new compound

I am extremely interested in this one. I supposed I am most interested in the 6-isomer you mentioned (with the oxygen in the meta-position), due to the fact that 3-substituted amphetamines seem to be rather extraordinary psychostimulants, but this it also chill. I think that it might be a great MDMA replacement, as it may exhibit less neurotoxicity than MDMA itself. As the dihydrofuranyl ring is much more metabolically stable than a methylenedixoy moiety, we wouldn't generate the 3,4-dihydroxy- and quinone nasties of MDMA.

As for a name...hmm...how about para-dihydrofurano-amphetamine (PDFA), that way the other significant structural isomer can be meta-dihydrofurano-amphetamine (MDFA).
 
For those visually inclined, here is a pic of this molecule vs MDA.

MDA%20vs%20MDPA.bmp


I'm just curious if the active enantiomer is like MDA (i.e. the R-isomer is the active one) or if it follows the MDMA pattern (i.e. the S-isomer is the active one.)
 
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^ that would be interesting to know. entactogens are a bit odd.

perhaps it'll appear on the market as a 'legal' mdma replacement. and then 6 months later the beta-ketone will appear.
 
i just found an interesting abstract relating to this compound. it seems even the indan analogue produces mdma like effects. i wonder if shulgin has ever tested some of these compounds…

does anyone have the full text?
J Med Chem. 1993 Nov 12;36(23):3700-6.Links
Synthesis and pharmacological examination of benzofuran, indan, and tetralin analogues of 3,4-(methylenedioxy)amphetamine.

Monte AP, Marona-Lewicka D, Cozzi NV, Nichols DE.
Department of Medicinal Chemistry, School of Pharmacy and Pharmacal Sciences, Purdue University, West Lafayette, Indiana 47907.
Benzofuran, indan and tetrahydronaphthalene analogs of 3,4-(methylenedioxy)amphetamine (MDA) were prepared in order to examine the role of the dioxole ring oxygen atoms of MDA in interacting with the serotonin and catecholamine uptake carriers. The series of compounds was evaluated for discriminative stimulus effects in rats trained to discriminate saline from the training drugs (S)-(+)-MBDB (1c), MMAI (3), and (S)-(+)-amphetamine and for the ability to inhibit the uptake of [3H]serotonin, [3H]dopamine, and [3H]norepinephrine into crude synaptosome preparations. Behaviorally, the benzofuran and indan analogs 4-6 produced similar discriminative cues, whereas the tetralin derivative 7 did not fully substitute for the training drugs. The results in the in vitro pharmacology studies indicate that selectivity for 5-HT versus catecholamine uptake carriers may be modulated by the position and orientation of ring oxygen atoms. However, the nonoxygenated isostere 6 possessed high potency at all uptake sites examined. Enlargement of the saturated ring by one methylene unit to give the tetralin derivative resulted in a large (3-4-fold) reduction in activity at catecholamine sites.
Click to expand...
 
Yes they produce the appropriate responding in trained mice, but what we're really seeing is 5-HT release cues there. IAP and MDAI aren't any fun by themselves because 5-HT release by itself isn't fun without DA & NE joining the party too.
 
A related chemical,
2-(2,3-Dihydro-benzofuran-5-yl)-1-methyl-ethylamine
supposedly an analog(legal?) of MDA. Any reports on this?
 
I think thats the one F&B was on about, i think MGS drew the wrong isomer. From the erowid paper the one with the meta-oxygen looks very similar to MDA while the para-oxygenated isomer looks a lot more serotonergic.
 
MattPsy said:
IAP and MDAI aren't any fun by themselves because 5-HT release by itself isn't fun without DA & NE joining the party too.
Click to expand...

:) DA & NE are always welcome @ "the party"
 
Fucking hell, I wrote a post and calculated some 5HT/DA/NE ratios of the different analogues, and now it's not here...
 
is NE really necessary for 'the magic'?
have you found a compound with good 5HT and DA activity and low NE releasing activity, refluxer? i think it should have less undesirable side effects than for example mdma…
 
Good report! I'd love to try something like this. Thank god for designer drugs, there's gonna be an explosion in things like these in the next 5-10 years.
 
testing the waters

just got my sample in.

testing the waters to see if i don't get an allergic reaction ,
took 1 mg (with my variable scale this could also be 2 mg)

taking it easy
but will post more news in the next few weeks.

kiss kiss
 
I was think maybe a good name for this compount could be 3,4-ethylenemonooxideamphetamine = EMA

And to clear things up about the position of the oxide you could say 4-EMA or EMA-4 en for it's analog with the oxide attached to the 3th-position you could say 3-EMA/ EMA-3, it's just an idea..
 
think about it years and years ago all rolls were just MDMA and not MDA....i wonder why...more economical.
 
Is 2-oxa-indan-5-yl-isopropylamine.hcl (an isomer of the subject of this thread) a stable compound? Looks loopy!
 
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