2-Fluoroamphetamine
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2-Fluoroamphetamine
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|---|---|
| Systematic (IUPAC) name | |
| 1-(2-fluorophenyl)propan-2-amine | |
| Clinical data | |
| Pregnancy cat. | ? |
| Legal status | ? |
| Identifiers | |
| CAS number | 1716-60-5  |
| ATC code | ? |
| PubChem | CID 121531 |
| ChemSpider | 108441 |
| Chemical data | |
| Formula | C9H12FN |
| Mol. mass | 153.196 |
| SMILES | eMolecules & PubChem |
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2-Fluoroamphetamine (2-FA) is a stimulant drug from the amphetamine family which has rarely been sold as a designer drug.[1] In addition, both 2-fluorophenethylamine and amphetamine have been found to act as potent agonists at the trace amine-associated receptor TAAR1,[2] 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 structural isomers to 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.[3][4]
See also
- 2-Fluoromethamphetamine
- 2-Methylamphetamine (2-MA)
- 2-Methoxymethamphetamine (Methoxyphenamine)
- 3-Fluoroamphetamine (3-FA)
- 4-Fluoroamphetamine (4-FA)
References
- ^ 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.
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