N-Methylheliamine

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N-Methylheliamine
N-Methylheliamine.svg
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
EC Number
  • 683-442-2
PubChem CID
UNII
  • 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
  • CN1CCC2=CC(=C(C=C2C1)OC)OC
  • cation:C1C=2C(=CC(OC)=C(C2)OC)CC[NH+]1C
Properties
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).

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) (Ki = 29 μM). [2] [4]

Contents

See also

References

  1. ↑ 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).
  2. 1 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. ↑ 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.
  4. ↑ 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.


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