1-(2H-1,3-benzoxathiol-5-yl)propan-2-amine

[Fertile]

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ibb.co

Anyone know if Nichols, Shulgin or Helm made this?

I haven't seen many examples of different rings or S in the meta position. I guess the S is liable to oxidation... but it does promise potent SERT activity.

 

[fastandbulbous]

With the para substituted methylthio compounds, the methylthio fits into MAO's active site, but the fuck off sized sulphur atom prevents conformational change to the active enzyme (why 2C-T-7 proved so toxic. All 4-methylthio sub PEAs are effecient MAOIs)
It's put me off any possible sulphur based MDMA analogues

 

[paracelsius]

How you gonna make it tho? unless the benzothiooxolane is available somehow. I suspect it might be closer to N-methyl-2-naphthylpropylamine. That compound is quite potent10x mdma with similar SERT NE DAT selectivity. precursor 2-acetylnaphthalene is cheaper than dirt. they used it in food as flavoring agent. I once inquire from India and they told me minimum order is 250kg (quarter of a ton!!!! I was like: noooo I wont need that much!!!

 

[Fertile]

Good question.

1,3-Benzoxathiole is commercially available. From their, tri(o-tolyl)phosphine + tributyl tin methoxide + isopropyl acetate + PdCl2 will result in a mixture of the BTPCP and an unwanted (ortho) positional isomer.

Exactly the same way 6-APB was made.

I presume the above is a name reaction, but I didn't search, I just checked that their WAS a facile route.

You will note that I placed the S at the meta position rather than the para. I HAD thought that it was the S at the para that was the issue but fast&bulbous, I'm sure, knows more than me.

The funny thing is that the 5/6 APB synthesis is in a patent! No RC vendor 'invented' it, they just undertook a lot of datamining. Nothing wrong with that EXCEPT when it's presented as new work.

 

[fastandbulbous]

Not sure how a meta sulphur atom would play out, as MDA/MDMA only works so well because the 5 membered ring holds the meta oxygen atom for one of the lone pairs to interact so well (why 6-APB is so much better an MDMA/MDA replacement). Sulphur atom is so much bigger, don't know if lone pair is in right position (may still be a potent MAOI).

 

[Didgital]

Check and google this.

(2-Aminopropyl)benzo[β]thiophenes (APBTs) are novel monoamine transporter ligands that lack stimulant effects but display psychedelic-like activity in mice

http://researchonline.ljmu.ac.uk/id/eprint/15682/

 

[Didgital]

Oh snap I messed up, the compounds in that paper are actually are Sulfur to carbon to carbon ring, more resembling of APBs, not Sulfur to Carbon to Oxygen. But they do have one that has sulfur in the meta position, the 6-APBT.

 

[Rectify]

Does Not Exist, It Seems.

 

[SectuNNDMT]

iv tried 6APB is it was awesome 5APB is psychedelic and empathogen MDMA like drug in one last pretty long