Salsolidine

Last updated
Salsolidine
Salsolidine v2.svg
Names
IUPAC name
6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline
Other names
1,2,3,4-Tetrahydro-6,7-dimethoxy-1-methyl-isoquinoline; DMMH-4; 6,7-Dimethylsalsolinol; O-Methylsalsoline; Norcarnegine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
EC Number
  • 837-124-7
PubChem CID
  • InChI=1S/C12H17NO2/c1-8-10-7-12(15-3)11(14-2)6-9(10)4-5-13-8/h6-8,13H,4-5H2,1-3H3
    Key: HMYJLVDKPJHJCF-UHFFFAOYSA-N
  • COc1cc2C(C)NCCc2cc1OC
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).

Salsolidine, also known as 6,7-dimethylsalsolinol, O-methylsalsoline, or norcarnegine, is a tetrahydroisoquinoline alkaloid found in various cactus species. [1] [2] It is pharmacologically active. [1] Salsolidine has been found to act as a weak but relatively potent monoamine oxidase inhibitor (MAOI), specifically of monoamine oxidase A (MAO-A) ((R)-enantiomer Ki = 6 μM), among other actions. [1] [3]

Contents

See also

References

  1. 1 2 3 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.
  2. ↑ 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.
  3. ↑ 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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