• Trip Reports Moderator: M!$ter-ED

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

fastandbulbous

Bluelight Crew
Joined
Jul 29, 2004
Messages
21,324
Location
that rainy little island off europe
A while ago, on a different forum, I suggested that the compound 5-(2-aminopropyl)-2,3-dihydrobenzofuran hydrochloride might just have a really promising entactogenic activity based on SAR studies from Dave Nichols on MDA/MDMA & analogues. After much headscratching & conversations with friends who have impressive synthetic skills, I eventually have a real bioassay of this particular compound; it's damn nice when you're sort of proved right in these matters!

Jpeg attached at bottom for easier identification of compound in question

Anyway, the bit you've been waiting for...

5-(2-aminopropyl)-2,3-dihydrobenzofuran hydrochloride compares favorably to MDMA at an oral dose of 150 mg - 225 mg.

The chronology of the compound: first signs of activity noted at about T+1h, smoothly developing into a deeply hedonic plateau from T+2 to T+4, then gently tapering off over the next several hours. No adverse effects noted other than mild nystagmus; sleep possible at any point after the plateau.

The effects are similar to those of MDMA but do not appear to involve the same degree of dopaminergic edge. There is increased empathy and profound contentment, and a luxurious sense of tactile enhancement. However, unlike with MDMA, there is no drive towards speech or locomotor activity -- even though I would not characterize the compound as sedative in any way.

One last interesting note: upon waking up at T+20 there are still feelings of being off-baseline: some lingering mood elevation, alteration of the visual field, and faint suggestions of a psychedelic effect. These feelings are pleasant (although not very distinct).


All in all, pretty much as I anticipated it would be from extrapolating SAR data for related entactogens. The next obvious step(s) would be a) the N-methyl derivative (analogous to the jump from MDA to MDMA) & b) moving the 2-aminopropyl side chain to the 6 position as this would give a compound which should be a lot more dopaminergic/MDA-like activity than this compound (and it's subsequent N-methylation).

Obviously, if someone else has actually synthesized the compounds mentioned in the above 'next steps', don't be shy - tell us about it and any possible human psychopharmacology =D .

substancecode_obscure
 

Attachments

  • 5-(2-aminopropyl)-2,3-dihydrobenzofuran.JPG
    5-(2-aminopropyl)-2,3-dihydrobenzofuran.JPG
    43.5 KB · Views: 360
Last edited by a moderator:
Wow! thanks a lot for the report :)

How can we simplify this name to standardize it to shulgin lingo - ie. to have it end with "amphetamine" and have a short acronym? Unless, of course, we want it to remain obsecure in order to try our best to dodge analogue laws? ;)

Also, is there any info as to whether the Serotonin depletion is long term (a la MDMA) or short term (a la 4-FA)?

Have you felt any kind of "crash" after the effects wore off?
 
I'd be interested in the thiolated version of this one, as well.
 
How can we simplify this name to standardize it to shulgin lingo - ie. to have it end with "amphetamine" and have a short acronym

Anybody have any suggestions? Never really thought about it!


Also, is there any info as to whether the Serotonin depletion is long term (a la MDMA) or short term (a la 4-FA)?

None - I've seen nothing about this compound other than bits at 'The Hive' years ago


how does this compound compare to 4-FMP (4-FA)?

Not a clue, I've no experience of 4-FA/4-FMP
 
Last edited:
Jamshyd said:
How can we simplify this name to standardize it to shulgin lingo - ie. to have it end with "amphetamine" and have a short acronym? Unless, of course, we want it to remain obsecure in order to try our best to dodge analogue laws? ;)

Shulgin would probably leave this as is, like F-2/F-22. As for a nickname, maybe F-x? Hmmm.
 
So the only difference between this and MDA is that missing oxygen there at position 3?

Difficult to synthesize?

Now if its very MDMA like already, but resembles MDA (..well when you look at the pic), any guess as to what N-methylation might do?
 
Jamshyd said:
Wow! thanks a lot for the report :)

How can we simplify this name to standardize it to shulgin lingo - ie. to have it end with "amphetamine" and have a short acronym? Unless, of course, we want it to remain obsecure in order to try our best to dodge analogue laws? ;)

Also, is there any info as to whether the Serotonin depletion is long term (a la MDMA) or short term (a la 4-FA)?

Have you felt any kind of "crash" after the effects wore off?

3,4-ethyleneoxyamphetamine?

Just a wild guess, I'm not too great on nomenclature.
 
Difficult to synthesize?

Not the person to ask, but I could try and get an answer from someone (I could make an educated guess).

As to what N-methylation would do, I'd reckon it would up the serotonogic effects, but I'm not sure about it's effects on dopaminergic activity.

Shulgin would probably leave this as is, like F-2/F-22. As for a nickname, maybe F-x? Hmmm.

If anything maybe 4-ODA for 3,4-oxydimethyleneamphetamine (the one with the 2-aminopropyl group in the 6-position would be 3-ODA, the number at the beginning indicating where the oxygen was positioned). Alternatively, if having the word amphetamine in isn't important, you could just go for 5-APDB & 6-APDB for 5 & 6-(2-aminopropyl)-2,3-dihydrobenzofuran

3,4-ethyleneoxyamphetamine

Makes it awkward to distinguish between 5-APDB & 6-APDB (unless you can think of an easy way as I quite like 3,4-EOA!)
 
This looks like an interesting RC but compared to MDA I am guessing that it is way more expensive to make. What would it take to get some unsaturation going on across the 2,3 position? I would think that there must be some mild oxidative step that could be done here since it leads to aromaticity.

The N-methylated analog looks pointless here, IMO.
 
nomeculture for this compound : how about 4-desoxy-mda ?
 
Last edited:
Cool! Thanks for bumping this ex-amine!

Yeah i was gonna say move the aminopropane chain to the 6 position, makes it an analog of one nichols made - 3-MeO-4-methyl-amphetamine, said to have a favorable monoamine releasing profile.

Dont know if you saw in one of the threads in ADD, but Nichols made the tetrahydronaphthylamine below and found it to be without activity. I really liked your acid dragonflies... thread and thought this one should be really active as the amine is locked in (almost) the same conformation as in lsd. Maybe saturation of the furan knocks it out of place just enough though. Would have been nice if they could have kept it unsaturated, or not used the furan altogether and stuck with the simpler 2,5-dimethoxy substitution.

Also, Nichols made this 5,8-dimethoxytetrahydronaphthylamine but dismissed it as inactive apparently without ever brominating it.

Can you see if your friend(s) are up for synthing the indole analog i've drawn? Would be really interested to see if it works, though i imagine it would be tricky.
 

Attachments

  • untitled.gif
    untitled.gif
    4 KB · Views: 204
I am glad there are people out there that know what they are doing living with shulguns spirit! The government will have to outlaw basic elements like nitrogen or oxygen soon to keep pace with chemists. :)
 
Have to ban chemistry research, nothing like this is being made by people in their garages or organised crime.
 
Why would the N-methylated version be worthless? I thought that on all of these amphetamine derivates that the N-methyl were more serotonergic in nature?

dorothyperkins- I think (not sure now...) that the dimethoxy analogue you drew was inactive. I'm pretty sure it was tested by a friend of mine, but I think there might have been another methyl on it, in a position analogous to amphetamine.

I'd have to double check, but AFAIK, those sorts have been a bit disapointing.
 
the 5,8-dimethoxy-2-naphthylamine? yeah nichols made it and it was basically inactive, i wouldn't expect it to be active though without brominating the ring.
 
The effects are similar to those of MDMA but do not appear to involve the same degree of dopaminergic edge. There is increased empathy and profound contentment, and a luxurious sense of tactile enhancement. However, unlike with MDMA, there is no drive towards speech or locomotor activity

Sounds similar to MBDB
 
Top