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| Trade names | 3FPPA |
| Addiction liability | moderate[1] |
| Routes of administration | Oral |
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| Legal status | |
| Pharmacokinetic data | |
| Onset of action | 20 - 60 minutes |
| Eliminationhalf-life | 90 minutes |
| Duration of action | 2 - 3 hours"3-FA".Psychonautwiki.[unreliable medical source?] |
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| Chemical and physical data | |
| Formula | C9H12FN |
| Molar mass | 153.200 g·mol−1 |
| 3D model (JSmol) | |
| Density | 1.0[2] g/cm3 |
| Boiling point | 208.2[2] °C (406.8 °F) |
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3-Fluoroamphetamine (3-FA;PAL-353) is astimulant drug from theamphetamine family which acts as amonoaminereleaser with similar potency tomethamphetamine but more selectivity fordopamine andnorepinephrine release overserotonin.[3] It is self-administered by mice to a similar extent to related drugs such as 4-fluoroamphetamine and 3-methylamphetamine.[4]
3-Fluoroamphetamine often found its use as adesigner drug in several studies to mimic the effects of illegal amphetamines.[5] It has also appeared on the drug market for recreational use as an amphetamine alternative, its has been reported in January 2009 to the European Early Warning System by Belgium. Little is known about the exact history of this compound.[6]
3-Fluoroamphetamine is a synthetic molecule of thesubstituted 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-methylatedphenethylamines.[citation needed] Substituted amphetamines can be synthesised by substituting a hydrogen atom with a substituent which in 3-fluoroamphetamines case is a fluorine atom positioned on the third carbon of thephenyl ring.3-Fluoroamphetamine has a chemical formula of C9H12FN. At room temperature it is a liquid withmolecular mass of 153.200 g·mol−1.[7]
3-Fluoroamphetamine is a locomotor stimulant that acts as a substrate-based releaser, with selectivity fordopamine overserotonin. This rank order is about the same as foramphetamine when tested in non-human primates.[8] The halflife was also comparable to amphetamine when tested in rats, namely 91 minutes. 3-Fluoroamphetamine is a good candidate fortransdermal administration since it is a relatively small molecule with a low melting point, has a weak basicity (pKa of 10) and is moderatelylipophilic. These properties make it easier to get through thestratum corneum, which is the lipid-rich outermost barrier of the skin.[9] By replacing a hydrogen in the ring with a fluorine, the compound is more likely to permeate theblood 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.[10]
Like other amphetamine derivatives, 3-fluoroamphetamine acts as amonoamine releaser with a higher selectivity fordopamine andnorepinephrine overserotonin.[11] There are multiple targets at whichamphetamines can disrupt the normal function of theseneurotransmitters. First, 3-fluoroamphetamine can interact with their respective transmembranemonoamine transporters DAT, NET, and SERT to mediate neurotransmitter release and reuptake.[10] It does this by blocking these transmembrane transporters, which usually transport monoamines back into the presynapse from the synaptic cleft. Blocking of DAT, NET, and SERT causes prolonged elevated concentrations of dopamine, norepinephrine, and serotonin in the synaptic cleft, causing more stimulant effects associated with theseneurotransmitters.[citation needed]
Another way for amphetamine derivatives to influence neurotransmission is by entering the presynapse via DAT, NET, and SERT, where the amphetamine derivative accumulates inside theneuron and replaces monoamines insynaptic vesicles by interacting with vesicularmonoamine transporter VMAT2. The concentration of free monoamines in the presynapse increases, prohibiting the inward transport of monoamines and encouraging the outward transport. Furthermore, amphetamine derivatives inhibit the action of mitochondrial monoamine oxidases (MOA), which catalyze the degradation of cytosolic monoamines. Inhibition thus increases cytosolic concentrations of monoamines even more.[12]
The mechanism of action for 3-fluoroamphetamine has not been individually studied yet, but various sources suggest that amphetamine derivatives generally have the same mechanism of action inmonoaminergic neurons .[12] However, further investigation on 3-fluoroamphetamine could reveal more specific mechanisms in which this amphetamine derivative modulates processes within the body.
3-Fluoroamphetamine is distinguished by its potent stimulant and mild entactogenic effects, setting it apart from otheramphetamines such as4-FA,2-FA, and2-FMA. It lacks the productivity and focus-enhancing properties reported for2-FA and2-FMA, potentially limiting its appeal and availability.[citation needed] Beyond its recreational use, 3-fluoroamphetamine has been identified as a nonselective inhibitor of dopamine and serotonin reuptake, with research suggesting its potential to inhibitcancercell proliferation in vitro and promote the release ofgrowth factors inneural contexts.[13][14] These findings point to its utility in neuropharmacological research and possible applications in treatingobesity,cancer, andcocaine dependency.[14][1]
As of October 2015 3-fluoroamphetamine is a controlled substance inChina.[15]
3-Fluoroamphetamine is controlled under theNpSG (New Psychoactive Substances Act)[16] as of November 26, 2016.[17] Production and import with the aim to place it on the market, administration to another person and trading is punishable.
New Zealand
3-Fluoroamphetamine is an amphetamine analogue, so is a Schedule 3Class C controlled substance in New Zealand.[18]
Switzerland
3-Fluoroamphetamine is a controlled substance specifically named under Verzeichnis E.[19]
Turkey
3-Fluoroamphetamine is a classed as drug and is illegal to possess, produce, supply, or import.[20]
United Kingdom
3-Fluoroamphetamine is considered a Class A drug as a result of the amphetamine analogue clause of theMisuse of Drugs Act 1971.[21]
United States: 3-Fluoroamphetamine may be considered to be an analog of amphetamine, thus falling under theFederal Analogue Act. 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 for human consumption.
