Chemistry:Gramine
Gramine (also called donaxine) is a naturally occurring indole alkaloid present in several plant species. Gramine may play a defensive role in these plants, since it is toxic to many organisms.[1]
Occurrence
Gramine has been found in the giant reed, Arundo donax,[2][3] Acer saccharinum (Silver Maple),[4] Hordeum,[1][3] (a grass genus that includes barley) and Phalaris[3] (another grass genus).
Effects and toxicity
Gramine is a close analogue of the psychedelic drug dimethyltryptamine (DMT), but its side chain has one less carbon atom in comparison.[5] In contrast to DMT, gramine does not have significant psychedelic-like behavioral effects in animals.[5] The same is true of 5-methoxygramine (5-MeO-gramine), which failed to substitute for DOM in rodent drug discrimination tests.[6]
Gramine has been found to act as an agonist of the adiponectin receptor 1 (AdipoR1).[7]
The LD50 of gramine is 44.6 mg/ kg iv in mice and 62.9 mg/ kg iv in rats.[8] Numerous studies have been done on the toxicity of gramine and tryptamines to insects harmful to crops in order to assess their potential use as an insecticide.[9]
Recent toxicity evaluations show Gramine to be relatively low toxicity in humans, and to have anti-mutagenic and potential neuroprotective action, as a widely found alkaloid present in Oats and Barley.[10] There are numerous recent studies on the potential health benefits of Gramine.
See also
- Dimethyltryptamine (DMT)
References
- ↑ 1.0 1.1 Corcuera, L. J. (1993). "Biochemical Basis of the Resistance of the Barley to Aphids". Phytochemistry 33 (4): 741–747. doi:10.1016/0031-9422(93)85267-U.
- ↑ Orechoff, A.; Norkina, S. (1935). "Über die Alkaloide von Arundo Donax L.". Berichte der Deutschen Chemischen Gesellschaft 68 (3): 436–437. doi:10.1002/cber.19350680312.
- ↑ 3.0 3.1 3.2 Cheeke, P. R. (1989). Toxicants of Plant Origin, Alkaloids. CRC Press. p. 172. ISBN 0-8493-6990-8. https://books.google.com/books?id=eASgQyXq8xMC&pg=PA172.
- ↑ Pachter, I. J.; Zacharias, D. E.; Ribeiro, O. (1959). "Indole Alkaloids of Acer saccharinum (the Silver Maple), Dictyoloma incanescens, Piptadenia colubrina, and Mimosa hostilis". Journal of Organic Chemistry 24 (9): 1285–1287. doi:10.1021/jo01091a032.
- ↑ 5.0 5.1 "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. 1975. pp. 98–144. ISBN 978-0-85608-011-1. OCLC 2176880. https://bitnest.netfirms.com/external/Books/978-0-85608-011-1. "Other structural variations of interest include gramine (4.15), which contains only a one-carbon side-chain and is without significant behavioural activity (Gessner, Mcisaac, and Page, 1961; Ho, Mcisaac, An, Harris, Walker, Kralik, and Airaksinen, 1970)."
- ↑ "DOM-stimulus generalization to LSD and other hallucinogenic indolealkylamines". Eur J Pharmacol 86 (3–4): 453–459. January 1983. doi:10.1016/0014-2999(83)90196-6. PMID 6572591.
- ↑ "Identification of adiponectin receptor agonist utilizing a fluorescence polarization based high throughput assay". PLOS ONE 8 (5). 2013. doi:10.1371/journal.pone.0063354. PMID 23691032. Bibcode: 2013PLoSO...863354S.
- ↑ Erspamer, V. (1954). "Pharmacology of Indolealkylamines". Pharmacological Reviews 6 (4): 425–487. doi:10.1016/S0031-6997(25)07372-7. PMID 13236482. http://pharmrev.aspetjournals.org/content/6/4/425.abstract.
- ↑ Corcuera, L. J. (1984). "Effects of Indole Alkaloids from Gramineae on Aphids". Phytochemistry 23 (3): 539–541. doi:10.1016/S0031-9422(00)80376-3. Bibcode: 1984PChem..23..539C. https://repositorio.uchile.cl/handle/2250/156743.
- ↑ "Safety evaluation of an oat grain alkaloid gramine by genotoxicity assays" , Manash Pratim Pathak et al. Drug Chem Toxicol. 2018 Apr. https://pubmed.ncbi.nlm.nih.gov/28523965/
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