Chemistry:O-Methylanhalonidine

O-Methylanhalonidine
Names
	IUPAC name 6,7,8-trimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline
Identifiers
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:80670;
ChEMBL	ChEMBL1178706;
ChemSpider	533403;
KEGG	16705;
PubChem CID	613648;
	InChI 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;
	SMILES CC1C2=C(C(=C(C=C2CCN1)OC)OC)OC;
Properties
Chemical formula	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).
	Infobox references

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]

References

↑ 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. http://link.springer.com/10.1007/978-3-642-70128-3_4. Retrieved 20 May 2025.
↑ 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. doi:10.1021/np50047a001. ISSN 0163-3864. Bibcode: 1986JNAtP..49..745M. https://pubs.acs.org/doi/abs/10.1021/np50047a001. Retrieved 20 May 2025.
↑ 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). Mydriatic Productions/Better Days Publishing. https://troutsnotes.com/pdf/C13_CactusAlkaloids.pdf.
↑ "Synthesis, Pharmacological Characterization, and Binding Mode Analysis of 8-Hydroxy-Tetrahydroisoquinolines as 5-HT7 Receptor Inverse Agonists". ACS Chem Neurosci 16 (3): 439–451. February 2025. doi:10.1021/acschemneuro.4c00667. PMID 39836645.

External links

O-Methylanhalonidine - Isomer Design

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[Lundström1985-1] 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. http://link.springer.com/10.1007/978-3-642-70128-3_4. Retrieved 20 May 2025.

[MenacheryLavanierWetherly1986-2] 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. doi:10.1021/np50047a001. ISSN 0163-3864. Bibcode: 1986JNAtP..49..745M. https://pubs.acs.org/doi/abs/10.1021/np50047a001. Retrieved 20 May 2025.

[Trout2013-3] 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). Mydriatic Productions/Better Days Publishing. https://troutsnotes.com/pdf/C13_CactusAlkaloids.pdf.

[ChanPottieSimon2025-4] "Synthesis, Pharmacological Characterization, and Binding Mode Analysis of 8-Hydroxy-Tetrahydroisoquinolines as 5-HT7 Receptor Inverse Agonists". ACS Chem Neurosci 16 (3): 439–451. February 2025. doi:10.1021/acschemneuro.4c00667. PMID 39836645.

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