2-Fluoroamphetamine
2-Fluoroamphetamine (2-FA) is a stimulant drug from the amphetamine family which has been sold as a designer drug.[1] 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 this substitution.[2][3]
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| Formula | C9H12FN |
| Molar mass | 153.200 g·mol−1 |
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Pharmacology
Anorexiant dose (amount inhibiting food intake by 50% for 2 hours, given 1 hour earlier) = 15 mg/kg (rat; p.o.).[4]
Analgesic dose (50% inhibition of response to tail-clamp) = 20 mg/kg (mouse; i.p.).[4]
Effect on blood pressure: 0.5 mg/kg (rat; i.v.) produces an increase in BP of 29 mm.[4]
Toxicology
LD50 (mouse; i.p.) = 100 mg/kg.[4]
Legal Status
United States
The Federal Analogue Act, 21 U.S.C. § 813, is a section of the United States Controlled Substances Act, allowing any chemical "substantially similar" to an illegal drug (in Schedule I or II) to be treated as if it were also in Schedule I or II, but only if it is intended (ref 1) for human consumption. 2-FA may be considered to be an analog of amphetamine, thus falling under the Federal Analog Act.
China
As of October 2015 2-FA is a controlled substance in China.[5]
See also
- 2-Fluoromethamphetamine
- 2-Methylamphetamine (2-MA)
- 2-Methoxymethamphetamine (methoxyphenamine)
References
- Rösner P, Quednow B, Girreser U, Junge T (March 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.
- Smart BE (2001). "Fluorine substituent effects on bioactivity". Journal of Fluorine Chemistry. 109: 3–11. doi:10.1016/s0022-1139(01)00375-x.
- Ismail FM (2002). "Important fluorinated drugs in experimental and clinical use". Journal of Fluorine Chemistry. 118 (1–2): 27–33. doi:10.1016/s0022-1139(02)00201-4.
- Costa E, Garattini S (1970). Amphetamines and Related Compounds. New York: Raven Press. p. 28.
- "关于印发《非药用类麻醉药品和精神药品列管办法》的通知" (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.