5-Br-DMT: SYNTHESIS AND EFFECTS

Please enjoy a new article on marine psychedelics that I wrote with Jason Wallach. It details a synthetic route to 5-Br-DMT as well as TiHKAL-style analysis of the subjective effects of the compound in human experimenters.

SEA DMT

A DISCUSSION WITH ADAM GREEN & DANIEL PINCHBECK

SCREENING AT BRANDEIS UNIVERSITY

Dear Massachusettsians, tomorrow I will be screening select episodes of Pharmacopeia (as well as some new unaired footage) at Brandeis University. The screening will be followed by a Q&A and is free of charge. I hope to see you there.

FREDERIK HEINZ BARTH

I am looking to contact Frederik Heinz Barth, we had a written exchange in 2008 but I've since been unable to get messages to you. If you read this please send me an email as I would like to reconnect to ask a question about the synthesis of substituted 1,8-naphthyridines.

MARKOVNIKOV DIBROMIDE

I am contemplating some hypothetical difficulties in the synthesis of 2,5-dibromohexane from 1,5-hexadiene. I am aware that this is a simple reaction that can be achieved in many ways but I would like to accomplish it in such a way that a messy separation is minimally necessary, be it via selective chemical extraction, column chromatography, or fractional distillation. The main unwanted side-products in this synthesis would be the mixed-Markovnikov product and the full anti-Markovnikov product. My first option is simple bromination with (aq) HBr and an appropriate phase transfer catalyst or a similar reaction involving hydrogen bromide gas. My second option is oxymercuration-demurcuration yielding hexane-2,5-diol which can then be subjected to a high yielding and selective bromination with PBr3. The third option is acid catalyzed hydration to the diol with H2SO4 and water followed by bromination with PBr3.

I would prefer not to use hydrogen bromide gas or mercuric acetate (which will require recycling of the metallic mercury liberated during demercuration) and so I lean toward acid catalyzed hydration. Would anyone with practical experience using the above methods enlighten me regarding their relative regioselectivity for the Markovnikov product? I believe it would be something like this: oxymercuration-demurcuration>acid catalyzed hydration>HBr addition.

AMIDE REDUCTION

I'LL BE TALKING ABOUT CONSCIOUSNESS

This Thursday with Adam Green and Daniel Pinchbeck. I hope to see you there.