2-Furylethylamine

2-Furylethylamine (2-FEA or FEA) is a drug of the arylalkylamine family related to the substituted phenethylamines such as β-phenethylamine (PEA) and amphetamine.^[1] It is known to have similar pressor effects as amphetamine and strong constricting effects on the uterus in animals.^[1][2][3] The psychoactive effects of FEA in humans are unknown.^[1]

2-Furylethylamine

Clinical data
Other names	2-Furylethylamine; Furylethylamine; 2-Furan-2-yl-ethylamine; 2-Furanethanamine; 2-(2-Furyl)ethanamine; 2-(2-Aminoethyl)furan; 2-(Furan-2-yl)ethan-1-amine; Furfurylmethylamine
Identifiers
IUPAC name 2-(furan-2-yl)ethanamine
CAS Number	1121-46-6 86423-58-7 (HCl)
PubChem CID	1132863
ChemSpider	963066
ChEMBL	ChEMBL4552984
CompTox Dashboard (EPA)	DTXSID60360632
ECHA InfoCard	100.128.411
Chemical and physical data
Formula	C6H9NO
Molar mass	111.144 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1=COC(=C1)CCN
InChI InChI=1S/C6H9NO/c7-4-3-6-2-1-5-8-6/h1-2,5H,3-4,7H2 Key:ZQSLNSHMUQXSQJ-UHFFFAOYSA-N

Derivatives of FEA include α-Me-FEA (furylisopropylamine) and α,N-Me-FEA, among others.^[1][2] α-Me-FEA was less several-fold potent than amphetamine in animals and showed limited effects in humans.^[2] Analogues of FEA, besides β-phenethylamine (PEA) and amphetamine (α-Me-PEA), include TH-FEA, α-Me-TH-FEA, ThEA, thiopropamine (α-Me-ThEA), 3-ThEA, 2-(2-pyrrolyl)ethylamine (NEA), and α-Me-NEA, among others.^[1][2] Some of them are known to be active.^[1][2]

FEA was first synthesized by 1920.^[1][3] FEA and analogues were studied by Gordon Alles and colleagues, who discovered its pressor effects.^[1][2] FEA is not a controlled substance in the United States as of 2011.^[1]

• 
  Phenethylamine
• 
  Amphetamine
• 
  Thiopropamine