Top Qs
Timeline
Chat
Perspective
F (psychedelic)
Pharmaceutical compound From Wikipedia, the free encyclopedia
Remove ads
F, or F-1, also known as semi-fly, is a putative psychedelic drug of the phenethylamine, DOx, and benzofuran families.[1][2][3][4][5] 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.[1] It is also an analogue of DOH-FLY (FLY), but in contrast to F, DOH-FLY has the 5-methoxy group tethered at the 6 position and the 2-methoxy group has additionally been cyclized and tethered to the 3 position.[1] Despite the moniker "semi-fly", F is not technically a FLY compound as its tetrahydrofuran ring is attached at different positions than FLY series compounds.[3]
Remove ads
Use and effects
According to Alexander Shulgin in 2011, the effects of F in humans are unknown.[1] 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".[6] 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.[7]
Pharmacology
F showed an affinity (Ki) of 388 nM for the serotonin 5-HT2 receptor, which was 21-fold lower than that of DOM.[3][8] It fully substituted for LSD in rodent drug discrimination tests, albeit with about 14-fold lower potency than DOM.[1][3][4][9][8] 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".[10][11][12][5]
Remove ads
History
F was first described in the scientific literature by David E. Nichols and colleagues by 1981.[1][6] It was briefly described by Alexander Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved)[7] and was included as an entry in Shulgin's 2011 book The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds.[1]
Society and culture
Legal status
The drug was not an explicitly controlled substance in the United States as of 2011.[1]
Derivatives
Derivatives of F, including F-2 and F-22, are known.[7][1] They were described by Shulgin in his 1991 book PiHKAL (Phenethylamines I Have Known and Loved).[7][1] These compounds feature one or two methyl groups at the distal position of the attached tetrahydrofuran ring.[7][1] Both compounds were inactive as psychedelic drugs at the assessed doses in humans.[7][1] F was 3-fold more potent than F-2 in animal studies.[7]
Remove ads
See also
References
External links
Wikiwand - on
Seamless Wikipedia browsing. On steroids.
Remove ads