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4-Fluoroamphetamine

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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 YesY
Chemical data
Formula C9H12FN 
Mol. mass 153.20 g/mol
SMILES eMolecules & PubChem
 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[citation needed] market, although it is sometimes sold as a designer drug along with related analogues such as 2-fluoroamphetamine and 4-fluoromethamphetamine, among others.[1][2]

Contents

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.

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 was reported that amphetamine is metabolized chiefly by para-hydroxylation of the phenyl ring.[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

References

  1. ^ Rösner, P; Quednow, B; Girreser, U; Junge, T (2005). "Isomeric fluoro-methoxy-phenylalkylamines: a new series of controlled-substance analogues (designer drugs)". Forensic science international 148 (2–3): 143–56. doi:10.1016/j.forsciint.2004.05.003. PMID 15639609. 
  2. ^ Nagai, F; Nonaka, R; Satoh Hisashi Kamimura, K (2007). "The effects of non-medically used psychoactive drugs on monoamine neurotransmission in rat brain". European journal of pharmacology 559 (2–3): 132–7. doi:10.1016/j.ejphar.2006.11.075. PMID 17223101. 
  3. ^ a b Marona-Lewicka, D; Rhee, GS; Sprague, JE; Nichols, DE (1995). "Psychostimulant-like effects of p-fluoroamphetamine in the rat". European journal of pharmacology 287 (2): 105–13. doi:10.1016/0014-2999(95)00478-5. PMID 8749023.  edit
  4. ^ Nichols, DE; Johnson, MP; Oberlender, R (1991). "5-Iodo-2-aminoindan, a nonneurotoxic analogue of p-iodoamphetamine". Pharmacology, biochemistry, and behavior 38 (1): 135–9. doi:10.1016/0091-3057(91)90601-W. PMID 1826785.  edit
  5. ^ Huang X, Marona-Lewicka D, Nichols DE. (1992). "p-methylthioamphetamine is a potent new non-neurotoxic serotonin-releasing agent.". Eur J Pharmacol. 229 (1): 31–38. doi:10.1016/0014-2999(92)90282-9. PMID 1473561. 
  6. ^ Li, Q; Murakami, I; Stall, S; Levy, AD; Brownfield, MS; Nichols, DE; Van De Kar, LD (1996). "Neuroendocrine pharmacology of three serotonin releasers: 1-(1,3-benzodioxol-5-yl)-2-(methylamino)butane (MBDB), 5-methoxy-6-methyl-2-aminoindan (MMAi) and p-methylthioamphetamine (MTA).". The Journal of pharmacology and experimental therapeutics 279 (3): 1261–7. PMID 8968349. 
  7. ^ Murphy, J; Flynn, JJ; Cannon, DM; Guiry, PJ; McCormack, P; Baird, AW; McBean, GJ; Keenan, AK (2002). "In vitro neuronal and vascular responses to 5-hydroxytryptamine: modulation by 4-methylthioamphetamine, 4-methylthiomethamphetamine and 3,4-methylenedioxymethamphetamine.". European journal of pharmacology 444 (1–2): 61–7. doi:10.1016/S0014-2999(02)01586-8. PMID 12191583. 
  8. ^ Baumann, M. H.; Clark, R. D.; Woolverton, W. L.; Wee, S.; Blough, B.; Rothman, R. B. (2011). "In Vivo Effects of Amphetamine Analogs Reveal Evidence for Serotonergic Inhibition of Mesolimbic Dopamine Transmission in the Rat". Journal of Pharmacology and Experimental Therapeutics 337 (1): 218–225. doi:10.1124/jpet.110.176271. PMC 3063744. PMID 21228061. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=3063744.  edit
  9. ^ http://www3.lrs.lt/pls/inter3/dokpaieska.showdoc_l?p_id=349758
  10. ^ "Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 )". Internetowy System Aktów Prawnych. http://isap.sejm.gov.pl/DetailsServlet?id=WDU20111050614. Retrieved 17 June 2011. 
  11. ^ "The Misuse of Drugs Act 1971 (Modification) Order 1977". 1977-10-20. http://www.legislation.gov.uk/ukpga/1971/38/schedule/2#reference-c817436. Retrieved 2011-11-08. 

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