N-Methylheliamine

N-Methylheliamine
Names
	IUPAC name 6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline
	Other names 6,7-Dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline; 6,7-Dimethoxy-2-methyl-THIQ; O-Methylcorypalline; Oxymethylcorypalline
Identifiers
CAS Number	16620-96-5 ;
3D model (JSmol)	Interactive image; cation: Interactive image;
ChEBI	CHEBI:192040; cation: CHEBI:194516;
ChEMBL	ChEMBL1196025;
ChemSpider	25766;
EC Number	683-442-2;
PubChem CID	27694;
UNII	UK294JA983;
CompTox Dashboard (EPA)	DTXSID90168082 ;
	InChI InChI=1S/C12H17NO2/c1-13-5-4-9-6-11(14-2)12(15-3)7-10(9)8-13/h6-7H,4-5,8H2,1-3H3 Key: TXPPKWZEHFNZOE-UHFFFAOYSA-N; cation: InChI=1S/C12H17NO2/c1-13-5-4-9-6-11(14-2)12(15-3)7-10(9)8-13/h6-7H,4-5,8H2,1-3H3/p+1 Key: TXPPKWZEHFNZOE-UHFFFAOYSA-O;
	SMILES CN1CCC2=CC(=C(C=C2C1)OC)OC; cation: C1C=2C(=CC(OC)=C(C2)OC)CC[NH+]1C;
Properties
Chemical formula	C12H17NO2
Molar mass	207.273 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

N-Methylheliamine, also known as O-methylcorypalline or as 6,7-dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline, is a tetrahydroisoquinoline and cyclized phenethylamine alkaloid found in Pachycereus pringlei and other cacti.^[1]^[2]^[3] It is known to be a weak monoamine oxidase inhibitor (MAOI), specifically of monoamine oxidase B (MAO-B) (K_i = 29 μM).^[2]^[4]

References

^ Lundström, Jan (1983). "Chapter 6 Simple Isoquinoline Alkaloids". The Alkaloids: Chemistry and Pharmacology. Vol. 21. Elsevier. pp. 255–327. doi:10.1016/s0099-9598(08)60052-8. ISBN 978-0-12-469521-4. TABLE 1: SIMPLE ISOQUINOLINE ALKALOIDS [...] TABLE II SIMPLE ISOQUINOLINE ALKALOIDS IN THE FAMILY OF CACTACEAE [...] [...] Pachycereus pringlei (S. Wats) Br&R: Heliamine (10), Lemaireocereine (7), Tehaunine (34), Weberine (40), Tehaunine N-oxide (34a). In Pachycereus pringlei, heliamine (10), tehaunine (34), lemaireocereine (7), and weberine (40) were identified (59).
^ ^a ^b 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.
^ 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.
^ Bembenek ME, Abell CW, Chrisey LA, Rozwadowska MD, Gessner W, Brossi A (January 1990). "Inhibition of monoamine oxidases A and B by simple isoquinoline alkaloids: racemic and optically active 1,2,3,4-tetrahydro-, 3,4-dihydro-, and fully aromatic isoquinolines". J Med Chem. 33 (1): 147–152. doi:10.1021/jm00163a025. PMID 2296014.