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FAEFHI

From Wikipedia, the free encyclopedia

Pharmaceutical compound
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
PubChemCID
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 as4-(2-aminoethyl)-5-hydroxyindole, is aserotonin receptor modulator of theindole group related toserotonin and othertryptamines.[1][2] It is apositional isomer of serotonin in which theethylamineside chain at the 3 position of the indolering system has been moved to the 4 position.[1][2] FAEFHI can also be thought of as a greatly simplifiedanalogue ofLSD and hencepartial ergoline.[1][2] Although FAEFHI shows significantaffinity forserotonin 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 concentrationsin vitro.[2] FAEFHI was first described in thescientific literature by 1984.[1][2]

See also

[edit]

References

[edit]
  1. ^abcdeOsman 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. Retrieved1 June 2025.
  2. ^abcdefWeinstein 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. Retrieved1 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). [...]


5-HT1
5-HT1A
5-HT1B
5-HT1D
5-HT1E
5-HT1F
5-HT2
5-HT2A
5-HT2B
5-HT2C
5-HT3–7
5-HT3
5-HT4
5-HT5A
5-HT6
5-HT7
Ergolines
(incl.lysergines)
Clavines
(6,8-dimethylergolines)
Lysergamides
(lysergic acid amides)
Ergopeptines
(peptide ergolines)
Partial ergolines
Related compounds
Natural sources


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