Carnegine

Last updated
Carnegine
Carnegine.svg
Names
IUPAC name
6,7-dimethoxy-1,2-dimethyl-3,4-dihydro-1H-isoquinoline
Other names
Pectenine; DMMM-4; 6,7-Dimethoxy-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline; 6,7-Dimethoxy-1,2-dimethyl-THIQ
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C13H19NO2/c1-9-11-8-13(16-4)12(15-3)7-10(11)5-6-14(9)2/h7-9H,5-6H2,1-4H3
    Key: HRSIPKSSEVRSPG-UHFFFAOYSA-N
  • CC1C2=CC(=C(C=C2CCN1C)OC)OC
Properties
C13H19NO2
Molar mass 221.300 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Carnegine, also known as pectenine, DMMM-4, or 6,7-dimethoxy-1,2-dimethyl-1,2,3,4-tetrahydroisoquinoline, is a tetrahydroisoquinoline and cyclized phenethylamine alkaloid found in Carnegiea gigantea , Pachycereus pringlei , and other cacti. [1] [2] [3] [4] [5] [6] [7]

Contents

It is known to be pharmacologically active, including acting as a relatively potent monoamine oxidase inhibitor (MAOI), specifically of monoamine oxidase A (MAO-A) (Ki = 2 μM for the (R)-enantiomer) but not of monoamine oxidase B (MAO-B), producing strychnine-like convulsions in animals, and having other actions and effects. [2] [3] [8] Carnegine and similar alkaloids might potentiate the effects of mescaline and related compounds like N-methylmescaline via their MAOI activity. [3] [2] [9]

The compound was first isolated in 1901 and its structure and synthesis were established in 1929. [4] [3]

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 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.
  3. 1 2 3 4 Cassels, Bruce K. (2019). "Alkaloids of the Cactaceae — The Classics". Natural Product Communications. 14 (1) 1934578X1901400123. doi: 10.1177/1934578X1901400123 . ISSN   1934-578X.
  4. 1 2 Reti, L. (1954). "Chapter 26 Simple Isoquinoline Alkaloids". The Alkaloids: Chemistry and Physiology. Vol. 4. Elsevier. p. 7–21. doi:10.1016/s1876-0813(08)60153-0. ISBN   978-0-12-469504-7 . Retrieved 20 May 2025.{{cite book}}: ISBN / Date incompatibility (help)
  5. ↑ Hodgkins JE, Brown SD, Massingill JL (April 1967). "Two new alkaloids in cacti". Tetrahedron Lett. 8 (14): 1321–1324. doi:10.1016/s0040-4039(00)90694-4. PMID   6044211.
  6. ↑ Pummangura, S.; McLaughlin, J. L.; Davis, D. V.; Cooks, R. G. (1982). "Cactus Alkaloids. XLIX. New Trace Alkaloids (Dehydrosalsolidine and Heliamine) From the Saguaro, Carnegiea gigantea, and Confirmation by Mikes (MS/MS)" . Journal of Natural Products. 45 (3): 277–282. Bibcode:1982JNAtP..45..277P. doi:10.1021/np50021a008. ISSN   0163-3864 . Retrieved 20 May 2025.
  7. ↑ 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.
  8. ↑ 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.
  9. ↑ Alexander Shulgin. Cacti: A Discourse by Sasha Shulgin. Mind States: Jamaica, October 1–6, 2002. Event occurs at 16:28–17:55, 25:45–28:44, [...]



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