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In his book PiHKAL (Phenethylamines I Have Known and Loved), Alexander Shulgin lists F-2's dose as greater than 15mg orally and its duration as unknown.[1] The drug produced no effects at assessed doses of up to 15mg.[1] Higher doses were not tested.[1] It is unknown whether F-2 is active.[1] On the other hand, David E. Nichols reported in 1981, via personal communication with Shulgin and M. Trampota in 1980, that F-2 was "shown to possess clinical activity".[2]
F-2 has been found to substitute for the psychedelic drugDOM in drug discrimination tests in rats.[1][3][4] However, it was about 40-fold less potent than DOM in this regard, requiring a dose of 5mg/kg.[1] For comparison, F-2 was tested in humans at doses of only up to 0.2mg/kg.[1] In contrast to the case of rats, F-2 at doses of up to 100mg/kg intraperitoneally in mice was without effects.[1] A dose of 150mg/kg intraperitoneally in mice was lethal.[1]
F-2 was first described in the scientific literature by David E. Nichols in 1981 via personal communication with Alexander Shulgin and M. Trampota in 1980.[2] Subsequently, it was described in greater detail by Nichols and colleagues in 1986[3] and 1991[4] and by Shulgin in his book PiHKAL (Phenethylamines I Have Known and Loved) in 1991.[1] Shulgin briefly alluded to F and its derivatives in a paper in 1971.[5]
12Nichols DE, Hoffman AJ, Oberlender RA, Riggs RM (February 1986). "Synthesis and evaluation of 2,3-dihydrobenzofuran analogues of the hallucinogen 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane: drug discrimination studies in rats". Journal of Medicinal Chemistry. 29 (2): 302–304. doi:10.1021/jm00152a022. PMID3950910.
12Nichols DE, Snyder SE, Oberlender R, Johnson MP, Huang XM (January 1991). "2,3-Dihydrobenzofuran analogues of hallucinogenic phenethylamines". J Med Chem. 34 (1): 276–281. doi:10.1021/jm00105a043. PMID1992127.
↑Shulgin AT (1971). "Preliminary studies of the synthesis of nitrogen analogs of Δ1-THC". Acta Pharm Suecia. 8: 680–681. Archived from the original on 2025-07-12. A preliminary study to this end has been the synthesis of a number of benzofuran and benzopyren counterparts. The synthesis of several methyl substituted furan compounds of the general formula: [structure] have been completed and some chemical problems associated with these syntheses will be discussed.
