O-Methylanhalonidine

Last updated
O-Methylanhalonidine
O-Methylanhalonidine.svg
Names
IUPAC name
6,7,8-trimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
  • InChI=1S/C13H19NO3/c1-8-11-9(5-6-14-8)7-10(15-2)12(16-3)13(11)17-4/h7-8,14H,5-6H2,1-4H3
    Key: VMFUYWSNWQYUTG-UHFFFAOYSA-N
  • CC1C2=C(C(=C(C=C2CCN1)OC)OC)OC
Properties
C13H19NO3
Molar mass 237.299 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

O-Methylanhalonidine is a tetrahydroisoquinoline alkaloid found in peyote (Lophophora williamsii) and various other cactus species. [1] [2] [3] It has been found to act as an inverse agonist of the serotonin 5-HT7 receptor. [4]

Contents

See also

References

  1. ↑ Lundström, J. (1985). "The Occurrence of Simple Isoquinolines in Plants". The Chemistry and Biology of Isoquinoline Alkaloids. Proceedings in Life Sciences. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 47–61. doi:10.1007/978-3-642-70128-3_4. ISBN   978-3-642-70130-6 . Retrieved 20 May 2025.
  2. ↑ Menachery, Mary D.; Lavanier, Gregory L.; Wetherly, Mark L.; Guinaudeau, Hélène; Shamma, Maurice (1986). "Simple Isoquinoline Alkaloids" . Journal of Natural Products. 49 (5): 745–778. Bibcode:1986JNAtP..49..745M. doi:10.1021/np50047a001. ISSN   0163-3864 . Retrieved 20 May 2025.
  3. ↑ Keeper Trout & friends (2013). Trout's Notes on The Cactus Alkaloids Nomenclature, Physical properties, Pharmacology & Occurrences (Sacred Cacti Fourth Edition, Part C: Cactus Chemistry: Section 1) (PDF). Mydriatic Productions/Better Days Publishing.
  4. ↑ Chan CB, Pottie E, Simon IA, Rossebø AG, Herth MM, Harpsøe K, Kristensen JL, Stove CP, Poulie CB (February 2025). "Synthesis, Pharmacological Characterization, and Binding Mode Analysis of 8-Hydroxy-Tetrahydroisoquinolines as 5-HT7 Receptor Inverse Agonists". ACS Chem Neurosci. 16 (3): 439–451. doi:10.1021/acschemneuro.4c00667. PMID   39836645.



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