What is 3-Fluoroamphetamine (3-FA)
3-Fluoroamphetamine (3-FA; PAL-353) is a stimulant drug from the amphetamine family which acts as a monoamine releaser with similar potency to methamphetamine but more selectivity for dopamine and norepinephrine release over serotonin.
It is self-administered by mice to a similar extent to related drugs such as 4-fluoroamphetamine and 3-methylamphetamine.
3-Fluoroamphetamine has been used as a designer drug in several studies to mimic the effects of illegal amphetamines.
It has also appeared on the drug market for recreational use as an amphetamine alternative, as was reported in January 2009 to the European Early Warning System by Belgium. Little is known about the exact history of this compound.
3-Fluoroamphetamine is a synthetic molecule of the substituted amphetamine class. Molecules in this class contain a phenethylamine core that consists of a phenyl ring, ethyl chain, a terminal amino (NH2) group and a methyl substitution at Rα.
Amphetamines themselves belong to the class of alpha-methylated phenethylamines.[citation needed] Substituted amphetamines can be synthesised by substituting a hydrogen atom with a substituent, which in 3-fluoroamphetamine’s case is a fluorine atom positioned on the third carbon of the phenyl ring.
3-Fluoroamphetamine has a chemical formula of C9H12FN. At room temperature it is a liquid with molecular mass of 153.200 g·mol−1
3-Fluoroamphetamine is a locomotor stimulant that acts as a substrate-based releaser, with selectivity for dopamine over serotonin. This rank order is about the same as for amphetamine when tested in non-human primates.
The half life was also comparable to amphetamine when tested in rats, namely 91 minutes. 3-Fluoroamphetamine is a good candidate for transdermal administration since it is a relatively small molecule with a low melting point, has a weak basicity (pKa of 10) and is moderately lipophilic.
These properties make it easier to get through the stratum corneum, which is the lipid-rich outermost barrier of the skin. By replacing a hydrogen atom in the ring with a fluorine, the compound is more likely to permeate the blood–brain barrier.
The P450 oxidase metabolism will most likely oxidize the 3-fluoroamphetamine at the 4 position, creating 3-fluoro-4-hydroxyamphetamine, which is hypothesized to be aversive to the intake of stimulants.
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