Tehaunine

Last updated
Tehaunine
Tehaunine.svg
Names
IUPAC name
5,6,7-trimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline
Other names
Tehuanine; 5,6,7-Trimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline; 5,6,7-Trimethoxy-2-methyl-THIQ
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
  • InChI=1S/C13H19NO3/c1-14-6-5-10-9(8-14)7-11(15-2)13(17-4)12(10)16-3/h7H,5-6,8H2,1-4H3
    Key: TUWJYOOVMLZJGJ-UHFFFAOYSA-N
  • CN1CCC2=C(C(=C(C=C2C1)OC)OC)OC
Properties
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).

Tehaunine, or tehuanine, also known as 5,6,7-trimethoxy-2-methyl-1,2,3,4-tetrahydroisoquinoline, is a tetrahydroisoquinoline and cyclized phenethylamine alkaloid found in Pachycereus pringlei and other cacti. [1] [2] [3]

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. ↑ 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.



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