N-Methylanhalinine

Last updated
N-Methylanhalinine
N-Methylanhalinine.svg
Names
IUPAC name
6,7,8-trimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline
Other names
1,2,3,4-Tetrahydro-6,7,8-trimethoxy-2-methylisoquinoline; O-Methylanhalidine
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C13H19NO3/c1-14-6-5-9-7-11(15-2)13(17-4)12(16-3)10(9)8-14/h7H,5-6,8H2,1-4H3
    Key: WMHZXZCCGOMWEQ-UHFFFAOYSA-N
  • CN1CCC2=CC(=C(C(=C2C1)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).

N-Methylanhalinine, also known as O-methylanhalidine, is a tetrahydroisoquinoline alkaloid found in various Turbinicarpus cactus species. [1] [2] [3] It has been found to act as a potent inverse agonist of the serotonin 5-HT7 receptor. [4] The compound is several-fold more potent as a serotonin 5-HT7 receptor inverse agonist than its parent compound anhalinine. [4]

Contents

See also

References

  1. ↑ Štarha, Roman; Chybidziurová, Adéla; Lacný, Zdenek (1999). "Alkaloids of the genus Turbinicarpus (Cactaceae)". Biochemical Systematics and Ecology. 27 (8): 839–841. Bibcode:1999BioSE..27..839S. doi:10.1016/S0305-1978(99)00019-8 . 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. ↑ Reti, L. (1954). "Chapter 26 Simple Isoquinoline Alkaloids". The Alkaloids: Chemistry and Physiology. Vol. 4. Elsevier. p. 7–21. doi:10.1016/s1876-0813(08)60153-0. ISBN   978-0-12-469504-7 . Retrieved 21 May 2025.{{cite book}}: ISBN / Date incompatibility (help)
  4. 1 2 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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