N-Methylheliamine

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]

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 Y
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

See also

• Substituted tetrahydroisoquinoline
• 3,4-Dimethoxyphenethylamine
• Pachycereus pringlei § Constituents and biological effects