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O-Methylanhalonidine

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O-Methylanhalonidine
Clinical data
Other names1-Methylanhalinine; 6,7,8-trimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline; 6,7,8-trimethoxy-1-methyl-THIQ
Drug classSerotonin 5-HT7 receptor inverse agonist
ATC code
  • None
Identifiers
  • 6,7,8-trimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline
PubChem CID
ChemSpider
KEGG
ChEBI
ChEMBL
Chemical and physical data
FormulaC13H19NO3
Molar mass237.299 g·mol−1
3D model (JSmol)
  • CC1C2=C(C(=C(C=C2CCN1)OC)OC)OC
  • 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

O-Methylanhalonidine, also known as 1-methylanhalinine, 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]

See also

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References

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  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 MD, Lavanier GL, Wetherly ML, Guinaudeau H, Shamma M (1986). "Simple Isoquinoline Alkaloids". Journal of Natural Products. 49 (5): 745–778. Bibcode:1986JNAtP..49..745M. doi:10.1021/np50047a001. ISSN 0163-3864.
  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, et al. (February 2025). "Synthesis, Pharmacological Characterization, and Binding Mode Analysis of 8-Hydroxy-Tetrahydroisoquinolines as 5-HT7 Receptor Inverse Agonists". ACS Chemical Neuroscience. 16 (3): 439–451. doi:10.1021/acschemneuro.4c00667. hdl:1854/LU-01JQ6WFR8R7G85440FRY2248HG. PMID 39836645.
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