4-Fluoroamphetamine

4-Fluoroamphetamine

Systematic (IUPAC) name
(RS)-1-(4-Fluorophenyl)propan-2-amine
Clinical data
Pregnancy cat.	?
Legal status	?
Routes	oral, insufflation
Identifiers
CAS number	459-02-9 N
ATC code	?
PubChem	CID 9986
ChemSpider	9592 Y
Chemical data
Formula	C9H12FN
Mol. mass	153.20 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C9H12FN/c1-7(11)6-8-2-4-9(10)5-3-8/h2-5,7H,6,11H2,1H3 Y Key:DGXWNDGLEOIEGT-UHFFFAOYSA-N Y
N (what is this?)  (verify)

4-Fluoroamphetamine (4-FA; PAL-303; "Flux",; "Flits", "R2D2"), also known as para-fluoroamphetamine (PFA) is a psychoactive drug and research chemical of the phenethylamine and amphetamine chemical classes. It produces stimulant and possibly entactogenic effects. 4-FA is a relatively rare drug on the illicit market^{[citation needed]}, although it is sometimes sold as a designer drug along with related analogues such as 2-fluoroamphetamine and 4-fluoromethamphetamine, among others.^[1][2]

Effects

The subjective effects of 4-FA include euphoria, increased energy, mood elevation, excessive talking, bruxism (jaw clenching), insomnia and suppressed appetite.

4-Fluoroamphetamine is a potent stimulant and serotonin releaser as with other para-substituted amphetamine derivatives, but is both significantly less potent as a serotonin releaser and much less neurotoxic than related compounds such as parachloroamphetamine.^{[citation needed]}

The dopamine reuptake inhibition produced by 4-FA is stronger than that of either PCA or PIA.^[3] 4-FA also produces less hyperthermia than similar compounds such as PMA, 4-MTA and 4-methylamphetamine.

Effects begin within an hour after ingestion. Common dose range is 75-150mg, usually taken orally. The chemical is active insufflated, though this is generally considered unfavorable because of the intense burn the chemical causes.

Neurotoxicity

The serotonin-releasing potency and neurotoxicity^{[citation needed]} of 4-fluoroamphetamine is less than for 4-chloroamphetamine.

Contrary to popular belief, neurotoxicity does not increase down the series of para-halogenated amphetamine derivatives^{[citation needed]}, even though serotonin releasing potency does follow this trend. For example, 4-iodoamphetamine is less toxic than is 4-chloroamphetamine.^[3][4] Hence, this property is not related to serotonin releasing potency as such, since PAL-287 was reported to be not at all neurotoxic even though it is a powerful 5-HT releasing agent.

Bearing in mind the above statements, it is unclear where 4-methylamphetamine fit in on the neurotoxicity scale. 4-MTA Is an example of a para-substituted, non-neurotoxic amphetamine.^[5][6][7]

Metabolism

Regarding the metabolic fate of 4-FA, it is likely excreted from the body entirely unchanged. The C-F bond at the 4-position on the phenyl ring likely resists deactivation in the liver by cytochrome P450 oxidase^[8]

Legality

• 4-fluoroamphetamine was banned in Lithuania in July 2009.^[9]
• 4-fluoroamphetamine has been banned in Switzerland the 1st December 2010, like many other research chemicals.
• 4-fluoroamphetamine is illegal in Sweden.
• 4-FA is illegal in Poland since 08.06.2011^[10]
• As a phenethylamine substituted by a halide, 4-fluoroamphetamine has been a class A drug in the UK since September 1977^[11]

See also

• 2-Fluoroamphetamine (2-FA)
• 3-Fluoroamphetamine (3-FA)
• 4-Fluoromethamphetamine (4-FMA)
• 4-Fluoromethcathinone (4-FMC)
• para-Bromoamphetamine (PBA)
• para-Chloroamphetamine (PCA)
• para-Iodoamphetamine (PIA)

References

v t e Neurotoxins Animal toxins Batrachotoxin Bestoxin Birtoxin Bungarotoxin Charybdotoxin Conotoxin Saxitoxin Tetrodotoxin Bacterial toxins Botulinum toxin Tetanospasmin Bacterial toxins Fungal toxins Bicuculline Plant toxins Penitrem A Picrotoxin Pesticides Rotenone Nerve agents Cyclosarin EA-3148 Novichok agent Sarin Soman Tabun (nerve agent) VE (nerve agent) VG (nerve agent) VM (nerve agent) VR (nerve agent) VX (nerve agent) Neurotransmitters and precursors Dopamine Glutamate L-Tyrosine L-Phenylalanine L-DOPA (Levodopa) L-Glutamine Neurotoxic drugs 1,4-BD 5,7-DHT 6-OHDA αET αMT Amphetamine Dizocilpine (MK-801) DSP-4 Ethanol GBL GHB Ibotenic Acid Ketamine Lisdexamfetamine Methamphetamine MBDB MDA MDEA MDMA (Ecstasy) MPP+ MPTP Norsalsolinol PBA PCA PIA Phencyclidine (PCP)