F (psychedelic)
pharmaceutical compound
F, or F-1, also known as 5-methoxy-6-(2-aminopropyl)-2,3-dihydrobenzofuran (5-methoxy-6-APDB), is a putative psychedelic drug of the phenethylamine, DOx, and benzofuran families. It is the derivative of 2,5-dimethoxyamphetamine (2,5-DMA or DOH) in which the 5-methoxy group on the benzene ring has been cyclized into a tetrahydrofuran ring tethered at the 4 position. It is also an analogue of DOH-5-hemiFLY, but in contrast to DOH-5-hemiFLY, F has the 5-methoxy group tethered at the 4 position rather than at the 6 position. While related to them, F is not a FLY compound as its tetrahydrofuran ring is attached at different positions than FLY series compounds.
Use and effects
According to Alexander Shulgin in 2011, the effects of F in humans are unknown. However, David E. Nichols reported in 1981, via personal communication with Shulgin and M. Trampota in 1980, that F was "shown to possess clinical activity". On the other hand, Shulgin reported in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved) that F was inactive at doses of up to 30 mg.
Interactions
Pharmacology
Pharmacodynamics
F showed an affinity (Ki) of 388 nM for the serotonin 5-HT2 receptor, which was 21-fold lower than that of DOM. It fully substituted for LSD in rodent drug discrimination tests, albeit with about 14-fold lower potency than DOM. In subsequent publications by the same research group, it was said that F failed to show LSD-like activity, was "nearly inactive in an in vivo behavioral assay for hallucinogen-like activity in rats", or had "dramatically attenuated LSD-like behavioral effects in rats".
Chemistry
Analogues
Analogues of F include DOET, 6-APDB, and MMDA-2, among others.
Derivatives
Derivatives of F, including F-2 and F-22, are known.
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This entry incorporates text from “F (psychedelic)” on English Wikipedia. Contributors are listed in the page history. Text is available under the Creative Commons Attribution-ShareAlike 4.0 License. Selected authority identifiers and statements are retrieved from Wikidata under CC0; their references and qualifiers remain part of the verification path.