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2-Fluoroamphetamine (2-FA) is a stimulant drug from the amphetamine family which has been sold as a designer drug. In addition, both 2-fluorophenethylamine and amphetamine have been found to act as potent agonists at the trace amine-associated receptor TAAR1, making it likely that 2-fluoroamphetamine also has significant activity at this receptor. 2-fluoroamphetamine differs from 3- and 4-fluoroamphetamine in the position of the fluorine atom on the aromatic ring, making them positional isomers of one another. The replacement of a hydrogen atom with a fluorine atom in certain compounds to facilitate passage through the blood–brain barrier, as is desirable in central nervous system pharmaceutical agents, is a common practice due to the corresponding increase in lipophilicity granted by the substitute.
Anorexiant dose (amount inhibiting food intake by 50% for 2 hours, given 1 hour earlier) = 15 mg/kg (rat; p.o.).
Analgesic dose (50% inhibition of response to tail-clamp) = 20 mg/kg (mouse; i.p.).
Effect on blood pressure: 0.5 mg/kg (rat; i.v.) produces an increase in BP of 29 mm.
LD50 (mouse; i.p.) = 100 mg/kg.
- 2-Methylamphetamine (2-MA)
- 2-Methoxymethamphetamine (Methoxyphenamine)
- 3-Fluoroamphetamine (3-FA)
- 4-Fluoroamphetamine (4-FA)
- Rösner, P; Quednow, B; Girreser, U; Junge, T (2005). "Isomeric fluoro-methoxy-phenylalkylamines: a new series of controlled-substance analogues (designer drugs)". Forensic Science International 148 (2–3): 143–56. doi:10.1016/j.forsciint.2004.05.003. PMID 15639609.
- Wainscott DB, Little SP, Yin T, Tu Y, Rocco VP, He JX, Nelson DL (January 2007). "Pharmacologic characterization of the cloned human trace amine-associated receptor1 (TAAR1) and evidence for species differences with the rat TAAR1". The Journal of Pharmacology and Experimental Therapeutics 320 (1): 475–85. doi:10.1124/jpet.106.112532. PMID 17038507.
- B.E. Smart (2001). "Fluorine substituent effects (on bioactivity". Journal of Fluorine Chemistry 109: 3–11.
- F.M.D. Ismail (2002). "Important ﬂuorinated drugs in experimental and clinical use". Journal of Fluorine Chemistry 118: 27–33.
- E. Costa and S. Garattini (1970) Amphetamines and Related Compounds, p.28, New York: Raven Press.
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