Chemistry:Carnegine
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]
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
- 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 2.2 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). Mydriatic Productions/Better Days Publishing. https://troutsnotes.com/pdf/C13_CactusAlkaloids.pdf.
- ↑ 3.0 3.1 3.2 3.3 Cassels, Bruce K. (2019). "Alkaloids of the Cactaceae — The Classics". Natural Product Communications 14 (1). doi:10.1177/1934578X1901400123. ISSN 1934-578X.
- ↑ 4.0 4.1 Reti, L. (1954). "Chapter 26 Simple Isoquinoline Alkaloids". The Alkaloids: Chemistry and Physiology. 4. Elsevier. p. 7–21. doi:10.1016/s1876-0813(08)60153-0. ISBN 978-0-12-469504-7. https://linkinghub.elsevier.com/retrieve/pii/S1876081308601530. Retrieved 20 May 2025.
- ↑ "Two new alkaloids in cacti". Tetrahedron Lett 8 (14): 1321–1324. April 1967. doi:10.1016/s0040-4039(00)90694-4. PMID 6044211.
- ↑ 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. doi:10.1021/np50021a008. ISSN 0163-3864. Bibcode: 1982JNAtP..45..277P. https://pubs.acs.org/doi/abs/10.1021/np50021a008. Retrieved 20 May 2025.
- ↑ 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.
- ↑ Alexander Shulgin. "Cacti: A Discourse by Sasha Shulgin". Mind States: Jamaica, October 1–6, 2002. https://archive.org/details/PsychedelicSalon025-sashashulgin-cacti.
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