2-Fluoroamphetamine

2-Fluoroamphetamine
Legal status
Legal status	CA: Schedule I; DE: NpSG (Industrial and scientific use only); UK: Class A;
Identifiers
	IUPAC name 1-(2-Fluorophenyl)propan-2-amine;
CAS Number	1716-60-5 ;
PubChem CID	121531;
ChemSpider	108441 ;
UNII	V8Q7K3989D;
CompTox Dashboard (EPA)	DTXSID30938009 ;
Chemical and physical data
Formula	C9H12FN
Molar mass	153.200 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(CC1=CC=CC=C1F)N;
	InChI InChI=1S/C9H12FN/c1-7(11)6-8-4-2-3-5-9(8)10/h2-5,7H,6,11H2,1H3 ; Key:GDSXNLDTQFFIEU-UHFFFAOYSA-N ;
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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]

Pharmacology

Anorexiant dose (amount inhibiting food intake by 50% for 2 hours, given 1 hour earlier) = 15 mg/kg (rat; p.o.).^[4]^{[medical citation needed]}

Analgesic dose (50% inhibition of response to tail-clamp) = 20 mg/kg (mouse; i.p.).^[4]^{[medical citation needed]}

Effect on blood pressure: 0.5 mg/kg (rat; i.v.) produces an increase in BP of 29 mm.^[4]^{[medical citation needed]}

Toxicology

LD₅₀ (mouse; i.p.) = 100 mg/kg.^[4]^{[medical citation needed]}

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]

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): 143–156. 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.
^ ^a ^b ^c ^d 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.

[1] 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): 143–156. doi:10.1016/j.forsciint.2004.05.003. PMID 15639609.

[smartfluorine-2] Smart BE (2001). "Fluorine substituent effects on bioactivity". Journal of Fluorine Chemistry. 109: 3–11. doi:10.1016/s0022-1139(01)00375-x.

[ismailfluorine-3] 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-4] Costa E, Garattini S (1970). Amphetamines and Related Compounds. New York: Raven Press. p. 28.

[5] "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.

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