Author Topic: possible opioid? 3(2-aminoethyl)2,3dihydro1benzofuran-7ol alkyl/dialkyl & esters (Read 77 times)

Naphyrone · « **on:** December 08, 2009, 09:45:19 AM »

So I have been up late and put the morphine molecule in Marvin sketch and proceeded to dissect it. While at the same time I was contemplating the indole opioids found in kratom and also how pethidine structure while not at first glance bares a faint resemblance to a stripped down morphine molecule, with these things in mind i continued to dissect away until I came to 3-(2-aminoethyl)-2,3-dihydro-1-benzofuran-7-ol. After checking to see if it fit the rule of 5 ok, it passed not violating a single rule meaning whatever it's effects on the body and mind may be it definitely would be active

. Now I have doubts that the amine alone would do much but how about a dimethyl? Now what if you do an esterification on the 7-alcohol? like heroin has. I have a deep feeling that this compound will be highly viable not to mention (currently)uncontrolled. Anyone have the equipment, chemicals and mice? Also adding a acetyl on the 2 position of the furan ring could have some interesting wanted qualities(still within the rule of 5).

[I know, I know! "green cows"]

Update: http://pubs.acs.org/doi/abs/10.1021/ja01189a032 (Morphine Studies. 2-Keto-7-methoxy-2,3-dihydrobenzofuran Derivatives)

Naphyrone · « **Reply #1 on:** December 08, 2009, 09:59:42 AM »

Update, for it to be closer to the morphine rule one may need a tertiary alcohol coming off the 3 position on the furan ring.
Something like the attached pic(3-[2-(dimethylamino)ethyl]-3-hydroxy-2,3-dihydro-1-benzofuran-7-yl acetate).

heisenberg · « **Reply #2 on:** December 14, 2009, 07:24:49 PM »

Here's the article you linked to:

Morphine Studies: 2-Keto-7-methoxy-2,3-dihydrobenzofuran Derivatives
E. C. Horning, R. U. Schock Jr.
J. Am. Chem. Soc., 1948, 70 (9), pp 2941–2944
DOI: 10.1021/ja01189a032

no1uno · « **Reply #3 on:** December 15, 2009, 01:40:25 PM »

Have just been looking (sorry, off-topic wander), but Rice stated (in his autobiographical musings in 'The Way of Synthesis')that when he was working with Dr Brossi on the phenolic oxidation of reticuline to salutaridine, he personally decided to investigate the Grewe cyclization, but with much stronger acids than had been used to date... In that respect he intended to try Triflic (~14.9 on the Hammett Scale) and then Fluorosulfonic acid (~15.1)...

In the circumstances, when he ran a tlc plate the next day (after putting the reagents in a bottle overnight) and found only the sought after cyclized product, he did not try Fluorosulfonic acid for the cyclization (as Triflic acid works)... For us, triflic acid is unobtanium, whereas flurosulfonic might not be... There is a Russian paper I've requested which says that Tetrafluoroethylene reacts with pyrosulfuric acid to give fluorosulfonic acid... PTFE (Teflon) gives TFE monomer on pyrolysis, so that is fucking nearly OTC

Author Topic: possible opioid? 3(2-aminoethyl)2,3dihydro1benzofuran-7ol alkyl/dialkyl & esters (Read 77 times)

Naphyrone

possible opioid? 3(2-aminoethyl)2,3dihydro1benzofuran-7ol alkyl/dialkyl & esters

Naphyrone

Re: possible opioid? 3(2-aminoethyl)2,3dihydro1benzofuran-7ol alkyl/dialkyl & esters

heisenberg

Re: possible opioid? 3(2-aminoethyl)2,3dihydro1benzofuran-7ol alkyl/dialkyl & esters

no1uno

Re: possible opioid? 3(2-aminoethyl)2,3dihydro1benzofuran-7ol alkyl/dialkyl & esters