4-Fluoroephedrine Explained
| Cas Number: | 63009-92-7 |
| Pubchem: | 95436263 |
| Chemspiderid: | 26701426 |
| Unii: | FUH6UKV9U8 |
| Synonyms: | 4-FEP; 4-Fluoro-β-hydroxy-N-methylamphetamine |
| Iupac Name: | (1S,2R)-1-(4-Fluorophenyl)-2-(methylamino)propan-1-ol |
| C: | 10 |
| H: | 14 |
| F: | 1 |
| N: | 1 |
| O: | 1 |
| Smiles: | C[C@H]([C@H](C1=CC=C(C=C1)F)O)NC |
| Stdinchi: | 1S/C10H14FNO/c1-7(12-2)10(13)8-3-5-9(11)6-4-8/h3-7,10,12-13H,1-2H3/t7-,10-/m1/s1 |
| Stdinchikey: | SPEQHEOLWDGWML-GMSGAONNSA-N |
4-Fluoroephedrine (4-FEP) is a "novel psychoactive substance" and substituted β-hydroxyamphetamine derivative related to ephedrine.[1] [2]
Pharmacology
Similarly to other amphetamines, 4-fluoroephedrine acts as a monoamine reuptake inhibitor and monoamine releasing agent.[3] It specifically acts as a selective norepinephrine releasing agent. In contrast to many other amphetamines, but similarly to most cathinones, 4-fluoroephedrine lacks affinity for the human trace amine-associated receptor 1 (hTAAR1).[4]
Chemistry
4-Fluoroephedrine, also known as 4-fluoro-β-hydroxy-N-methylamphetamine, is a substituted phenethylamine, amphetamine, and β-hydroxyamphetamine derivative. It is the 4-fluoro analogue of ephedrine.
The synthesis of 4-fluoroephedrine has been described.[5]
It can serve as a precursor in the synthesis of 4-fluoromethamphetamine (4-FMA).[6]
The predicted log P (XLogP3) of 4-fluoroephedrine is 1.0.[7] For comparison, the predicted log P of ephedrine is 0.9.[8]
History
4-Fluoroephedrine was first described in the scientific literature by 1991. The next mention of it in the literature was in 2013, when it was identified as a "novel psychoactive substance".[9] The pharmacology of 4-fluoroephedrine was characterized in 2015.
Other drugs
4-Fluoroephedrine is known to be a metabolite of 4-fluoromethcathinone (4-FMC; flephedrone).[10] [11]
Notes and References
- King LA . New phenethylamines in Europe . Drug Test Anal . 6 . 7–8 . 808–818 . 2014 . 24574327 . 10.1002/dta.1570 .
- Corkery JM, Schifano F, Martinotti G . How deaths can help clinicians and policy-makers understand the risks of novel psychoactive substances . Br J Clin Pharmacol . 86 . 3 . 482–498 . March 2020 . 31770457 . 7080619 . 10.1111/bcp.14183 .
- Rickli A, Hoener MC, Liechti ME . Monoamine transporter and receptor interaction profiles of novel psychoactive substances: para-halogenated amphetamines and pyrovalerone cathinones . Eur Neuropsychopharmacol . 25 . 3 . 365–376 . March 2015 . 25624004 . 10.1016/j.euroneuro.2014.12.012 .
- Simmler LD, Buchy D, Chaboz S, Hoener MC, Liechti ME . In Vitro Characterization of Psychoactive Substances at Rat, Mouse, and Human Trace Amine-Associated Receptor 1 . J Pharmacol Exp Ther . 357 . 1 . 134–144 . April 2016 . 26791601 . 10.1124/jpet.115.229765 .
- Mullen AJ . The synthesis and pharmacology of ephedrine analogues . 1991 . 12 September 2024.
- Rickli . Anna . Pharmacology of novel psychoactive substances . 2016 . 10.5451/UNIBAS-006616893 .
- Web site: 1-(4-Fluorophenyl)-2-(methylamino)propan-1-ol . PubChem . 12 September 2024.
- Web site: Ephedrine . PubChem . 12 September 2024.
- Archer JR, Dargan PI, Chan WL, Hitchings A, Hudson S, Wood DM . 201. Trend analysis of novel psychoactive substances detected in pooled urine samples from street urinals over six months . 2013 . Clinical Toxicology . 51 . 7 .
- Uralets V, Rana S, Morgan S, Ross W . Testing for designer stimulants: metabolic profiles of 16 synthetic cathinones excreted free in human urine . J Anal Toxicol . 38 . 5 . 233–241 . June 2014 . 24668489 . 10.1093/jat/bku021 . free .
- Fan SY, Zang CZ, Shih PH, Ko YC, Hsu YH, Lin MC, Tseng SH, Wang DY . A LC-MS/MS method for determination of 73 synthetic cathinones and related metabolites in urine . Forensic Sci Int . 315 . 110429 . October 2020 . 32784041 . 10.1016/j.forsciint.2020.110429 .
