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4-Hydroxygramine

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4-Hydroxygramine
Identifiers
  • 3-[(dimethylamino)methyl]-1H-indol-4-ol
CAS Number
PubChem CID
ChEMBL
Chemical and physical data
FormulaC11H14N2O
Molar mass190.246 g·mol−1
3D model (JSmol)
  • CN(C)CC1=CNC2=C1C(=CC=C2)O
  • InChI=InChI=1S/C11H14N2O/c1-13(2)7-8-6-12-9-4-3-5-10(14)11(8)9/h3-6,12,14H,7H2,1-2H3
  • Key:YJJMKVPZBCHYHD-UHFFFAOYSA-N

4-Hydroxygramine is a serotonergic and a serotonin antagonist belonging to the class of indole-3-methanamines, a family of indoles with a single-carbon chain that are related to tryptamines.[1][2]

Pharmacology

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Pharmacodynamics

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4-Hydroxygramine is an antagonist of several subtypes of 5-hydroxytryptamine receptors; it has a high affinity for the 5-HT2C receptor, with an affinity (Ki) of 24 ± 0.8 nM, followed by binding to the 5-HT2A and 5-HT2B receptors (with Ki values of 923 ± 224 and 1242 ± 295, respectively).[2]

See also

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References

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  1. ↑ Troxler F, Seemann F, Hofmann A (1959). "Abwandlungsprodukte von psilocybin und psilocin. 2. Mitteilung über synthetische indolverbindungen" [Synthetic indole compounds. II. Psilocybin and psilocin modifications]. Helvetica Chimica Acta (in German). 42 (6): 2073–2103. doi:10.1002/hlca.19590420638.
  2. 1 2 Sard H, Kumaran G, Morency C, Roth BL, Toth BA, He P, et al. (October 2005). "SAR of psilocybin analogs: discovery of a selective 5-HT 2C agonist". Bioorganic & Medicinal Chemistry Letters. 15 (20): 4555–4559. doi:10.1016/j.bmcl.2005.06.104. PMID 16061378.