O-Methylpellotine

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O-Methylpellotine
O-Methylpellotine.svg
Names
IUPAC name
6,7,8-trimethoxy-1,2-dimethyl-3,4-dihydro-1H-isoquinoline
Other names
6,7,8-Trimethoxy-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline; Pellotine methyl ester
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C14H21NO3/c1-9-12-10(6-7-15(9)2)8-11(16-3)13(17-4)14(12)18-5/h8-9H,6-7H2,1-5H3
    Key: SDLPOZWCCRGUOA-UHFFFAOYSA-N
  • CC1C2=C(C(=C(C=C2CCN1C)OC)OC)OC
Properties
C14H21NO3
Molar mass 251.326 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

O-Methylpellotine is a tetrahydroisoquinoline alkaloid found in various cactus species, such as Lophophora diffusa and Pachycereus weberi . [1] [2] It has been found to act as an inverse agonist of the serotonin 5-HT7 receptor. [3]

Contents

See also

References

  1. ↑ 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 21 May 2025.
  2. ↑ 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.
  3. ↑ 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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