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2-Furylethylamine

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Pharmaceutical compound
2-Furylethylamine
Clinical data
Other names2-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
ATC code
  • None
Identifiers
  • 2-(furan-2-yl)ethanamine
CAS Number
PubChemCID
ChemSpider
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.128.411Edit this at Wikidata
Chemical and physical data
FormulaC6H9NO
Molar mass111.144 g·mol−1
3D model (JSmol)
  • C1=COC(=C1)CCN
  • InChI=1S/C6H9NO/c7-4-3-6-2-1-5-8-6/h1-2,5H,3-4,7H2
  • Key:ZQSLNSHMUQXSQJ-UHFFFAOYSA-N

2-Furylethylamine (2-FEA orFEA) is adrug of thearylalkylamine family related to thesubstituted phenethylamines such asβ-phenethylamine (PEA) andamphetamine.[1] It is known to have similarpressor effects as amphetamine and strong constricting effects on theuterus in animals.[1][2][3] Thepsychoactive effects of FEA in humans are unknown.[1]

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

FEA was firstsynthesized by 1920.[1][3] FEA and analogues were studied byGordon Alles and colleagues, who discovered its pressor effects.[1][2] FEA is not acontrolled substance in theUnited States as of 2011.[1]

References

[edit]
  1. ^abcdefghiShulgin A, Manning T, Daley PF (2011)."#67. FEA".The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley, CA: Transform Press. pp. 138–141.ISBN 978-0-9630096-3-0.OCLC 709667010.
  2. ^abcdefAlles GA, Feigen GA (1941)."Comparative physiological actions of phenyl-, thienyl-, and furylisopropylamines".Journal of Pharmacology and Experimental Therapeutics.72 (3):265–275.doi:10.1016/S0022-3565(25)03876-5.
  3. ^abWindaus A, Dalmer O (1920). "Furethylamine and tetrahydrofurethylamine".Berichte Deutsch. Chem. Ges.53B:2304–2308.doi:10.1002/cber.19200531118.


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