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  N
PubChem CID	121531
ChemSpider	108441  Y
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 Y Key:GDSXNLDTQFFIEU-UHFFFAOYSA-N Y
NY  (what is this?)    (verify)

1 gram of 2-FA

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-fluoroamphetamine 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, if, as stated above, it is intended for human consumption.

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

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.
2. Smart BE (2001). "Fluorine substituent effects on bioactivity". Journal of Fluorine Chemistry. 109 (1): 3–11. Bibcode:2001JFluC.109....3S. doi:10.1016/s0022-1139(01)00375-x.
3. Ismail FM (2002). "Important fluorinated drugs in experimental and clinical use". Journal of Fluorine Chemistry. 118 (1–2): 27–33. Bibcode:2002JFluC.118...27I. doi:10.1016/s0022-1139(02)00201-4.
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.