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FAEFHI

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FAEFHI
Clinical data
Other names4-(2-Aminoethyl)-5-hydroxyindole
Drug classSerotonin receptor modulator; Partial ergoline
ATC code
  • None
Identifiers
  • 4-(2-aminoethyl)-1H-indol-5-ol
PubChem CID
ChemSpider
Chemical and physical data
FormulaC10H12N2O
Molar mass176.219 g·mol−1
3D model (JSmol)
  • C1=CC(=C(C2=C1NC=C2)CCN)O
  • InChI=1S/C10H12N2O/c11-5-3-8-7-4-6-12-9(7)1-2-10(8)13/h1-2,4,6,12-13H,3,5,11H2
  • Key:CSFAMKTUFIKJAE-UHFFFAOYSA-N

FAEFHI, also known as 4-(2-aminoethyl)-5-hydroxyindole, is a serotonin receptor modulator of the indole group related to serotonin and other tryptamines.[1][2] It is a positional isomer of serotonin in which the ethylamine side chain at the 3 position of the indole ring system has been moved to the 4 position.[1][2] FAEFHI can also be thought of as a greatly simplified analogue of LSD and hence partial ergoline.[1][2] Although FAEFHI shows significant affinity for serotonin receptors, it had much lower affinity than serotonin or tryptamine (171-fold lower than serotonin and 5-fold lower than tryptamine).[1][2] In addition, it did not show serotonin-like activity (i.e., serotonin receptor agonism) even at very high concentrations in vitro.[2] FAEFHI was first described in the scientific literature by 1984.[1][2]

See also

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References

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  1. ^ a b c d e Osman R, Mazurek AP, Weinstein H (18 January 1987). "Simulation of Molecular Stereoelectronic Mechanism for the Interaction of Hallucinogens and Indole Derivatives at 5-HT Receptors". Steric Aspects of Biomolecular Interactions. CRC Press. pp. 199–210. doi:10.1201/9781351076890-10. ISBN 978-1-351-07689-0. Retrieved 1 June 2025.
  2. ^ a b c d e f Weinstein H, Osman R, Topiol S, Ebersole BJ, Mazurek AP (12 March 1984). "Theoretical and experimental studies of drug-receptor interactions: Determinants for recognition of 5-hydroxytryptamine analogs". International Journal of Quantum Chemistry. 26 (S11): 183–194. doi:10.1002/qua.560260719. ISSN 0020-7608. Retrieved 1 June 2025. Two new compounds, 5-hydroxyaminotetrahydrobenzindole (FHATHBIN, 2 in Fig. l), and 4-(betu-aminoethyl)-5-hydroxyindole (FAEFHI, 3 in Fig. 1) provide additional opportunity to probe the hypotheses regarding recognition at high affinity 5-HT sites. FHATHBIN incorporates structural elements of the LSD molecule, but has an hydroxyl substituent in the 5-position instead of the C9-C10 double bond, while FAEFHI is an analog of 5-HT in which the aminoethyl side chain was moved from the 3-position of the indole, to the 4-position (see Fig. 1). Preliminary pharmacological data indicated that FHATHBIN had 5-HT-like activity at some receptors in the peripheral nervous system, while FAEFHI did not elicit 5-HT-like activity at concentrations far exceeding those at which 5-HT acted in the same systems [7]. [...] Figure 1. The molecular structures of 5-hydroxytryptamine (l), 5-hydroxyaminotetrahydrobenzindole (2), and 4-(bera-aminoethyl)-5-hydroxyindole (3). [...]



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