3-Fluoroethamphetamine

3-Fluoroethamphetamine (3-FEA) is a stimulant drug of the amphetamine class which acts as a releasing agent of the monoamine neurotransmitters norepinephrine, dopamine and serotonin.

3-Fluoroethamphetamine
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
IUPAC name
  • N-ethyl-1-(3-fluorophenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC11H16FN
Molar mass181.254 g·mol−1
3D model (JSmol)
SMILES
  • CC(CC1=CC(F)=CC=C1)NCC
InChI
  • InChI=1S/C11H16FN/c1-3-13-9(2)7-10-5-4-6-11(12)8-10/h4-6,8-9,13H,3,7H2,1-2H3 N
  • Key:CKPWHLGHHXSVJI-UHFFFAOYSA-N N
 NY (what is this?)  (verify)

Compared to the unsubstituted ethylamphetamine, 3-fluoroethamphetamine is a weaker releaser of noradrenaline, but a stronger releaser of both dopamine and serotonin, and produced the strongest reinforcing effects in animal studies out of a range of 3-substituted ethamphetamine derivatives tested, despite not being the most potent dopamine releaser.[1][2][3][4]

See also

References

  1. Tessel RE, Woods JH (1974). "Structural relationship between meta-substituted N-ethylamphetamines and self-administration in rhesus monkeys". Pharmacologist. 16: 142.
  2. Tessel RE, Woods JH, Counsell RE, Lu M (February 1975). "Structure-activity relationships between meta-substituted N-ethylamphetamines and locomotor activity in mice". The Journal of Pharmacology and Experimental Therapeutics. 192 (2): 310–8. PMID 1117418.
  3. Tessel RE, Rutledge CO (May 1976). "Specificity of release of biogenic amines from isolated rat brain tissue as a function of the meta substituent of N-ethylamphetamine derivatives". The Journal of Pharmacology and Experimental Therapeutics. 197 (2): 253–62. PMID 1271279.
  4. Tessel RE, Woods JH (May 1978). "meta Substituted N-ethylamphetamine self injection responding in the rhesus monkey: structure-activity relationships". The Journal of Pharmacology and Experimental Therapeutics. 205 (2): 274–81. PMID 417172.
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