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benzofuran homologues of known tryptamines

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E

entheogenic-gnosis

Rising Star
"Dimemebfe" (2-(5-Methoxy-1-benzofuran-3-yl)-N,N-dimethyltryptamine) is 5-MEO-DMT only the pyrrole ring has been swapped out with a furan ring, I've heard this reduces activity, but that these compounds (dimemebfe and 5-MeO-DiBF) are being used as research chemicals. My interest is mainly chemical but human activity interests me here as well because these compounds are being used as psychedelics, which provides unique insight into their activity that's far more useful that animal assays or binding affinity information...


I'm intrigued very much by these benzofuran homologues of known tryptamines, and looking for good information sources...

-EG
 
There are some successful reports out of 5-MeO-DIBF out there, which I was interested to read. It seems awfully dangerous, who knows how that oxygen is changing its behavior, especially adding in a rowdy 5-meo and diisopropyl group.

Tomaszewski Z1 said:
At the 5-HT2 receptor, the benzofurans had slightly decreased affinities, approximately one-third and one-sixth those of the indoles, for the primary amines and the tertiary amines, respectively. The benzofurans also had lower affinity at the 5-HT1A receptor, but decreased only about 20-30% from that of the indole isosteres. Thus, the 5-HT1A receptor is less discriminating with respect to preference for an indole versus a benzofuran, although all of the compounds did have higher affinities for the 5-HT2 receptor than for the 5-HT1A receptor.
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Tripsit is offering this factsheet
 
I see these benzofuran bioisosteres of known tryptamines as still very interesting, though they are quite a bit less potent than the indole bioisosteres, actually their pharmacology is fairly fascinating as well...Though I really don't see them as dangerous, at least not overtly, but yes until more research has been conducted I would discourage human experimentation.

Are there any benzothiophene bioisosteres of known active tryptamines? Since sulphur lies just below oxygen in the periodic table I feel these would be the next bioisosteres to investigate, and may be pharmocologically similar to the benzofuran compounds.

Perhaps you could even create indazole bioisosteres of known tryptamine compounds, which I would be particularly interested in.

-eg
 
For the record, correct nomenclature would be based around "3-(2-dimethylaminoethyl)benzofuran". :D

Your recent chemistry related posts have been interesting and enjoyable for me, eg.

entheogenic-gnosis said:
Are there any benzothiophene bioisosteres of known active tryptamines? [...]Perhaps you could even create indazole bioisosteres of known tryptamine compounds,
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This should be possible, indazole analogs of indolic cannabinoids already exist. And as for benzothiophenes, just take a look at Benocyclidine. Curious. Would the naphthalene analog be DRI or NMDARA or something else?

These are among a number of related things I've pondered over the years. It would take days to publish all the structures I've dreamed up. Its interesting to see this (fairly obvious) fantasy chemistry being put to the test in the material world.

EDIT: of course, this benzofuran thing would also apply to ergoline analogs. The chemistry gets a tad more complicated there, though.
 
Because of all the recent investigation into these position two substituted tryptamines/dimethyltryptamines I would be very much interested to see if any indazole bioisoteres of dimethyltryptamine have been synthesized and explored, as far as I can tell, there are not any.

This indazole compound was of interest, but still dissimilar from a dimethyltryptamine compound with its indole ring swapped out with an indazole ring as mentioned above:

(S)-2-(8,9-dihydro-7H-pyrano[2,3-g]indazol-1-yl)-1-methylethylamine also known as "AL-38022A" is an indazole derivative drug which is one of a range of similar drugs developed for scientific research and with some possible clinical applications. It acts as a potent and selective agonist for the 5-HT2 family of serotonin receptors, with highest binding affinity for the 5-HT2C subtype and around 4x less affinity for 5-HT2A and 5-HT2B. In drug discrimination tests on animals, it fully substituted for both DOM and 5-MeO-DMT. -wikipedia
 
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