Chemistry:N-Methylheliamine
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| IUPAC name
6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline
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| Other names
6,7-Dimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline; 6,7-Dimethoxy-2-methyl-THIQ; O-Methylcorypalline; Oxymethylcorypalline
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3D model (JSmol)
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| 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). | |
| 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) (Ki = 29 μM).[2][4]
See also
- Substituted tetrahydroisoquinoline
- 3,4-Dimethoxyphenethylamine
- Pachycereus pringlei § Constituents and biological effects
References
- ↑ Lundström, Jan (1983). "Chapter 6 Simple Isoquinoline Alkaloids". The Alkaloids: Chemistry and Pharmacology. 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)."
- ↑ 2.0 2.1 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.
- ↑ 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.
- ↑ "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. January 1990. doi:10.1021/jm00163a025. PMID 2296014.
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