Gramine

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title: "Gramine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["adiponectin-receptor-agonists", "indole-alkaloids", "dimethylamino-compounds", "plant-toxins"] topic_path: "general/adiponectin-receptor-agonists" source: "https://en.wikipedia.org/wiki/Gramine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

|Verifiedfields = changed |Watchedfields = changed |verifiedrevid = 415511050 |Name = Gramine |PIN = 1-(1H-Indol-3-yl)-N,N-dimethylmethanamine |OtherNames = donaxine |ImageFile_Ref = |ImageFile = Gramine.svg |ImageClass = skin-invert-image |ImageSize = 175px |ImageName = Chemical structure of gramine |Section1={{Chembox Identifiers |ChemSpiderID_Ref = |ChemSpiderID = 6625 |ChEBI_Ref = |ChEBI = 28948 |KEGG_Ref = |KEGG = C08304 |InChI = 1/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3 |InChIKey = OCDGBSUVYYVKQZ-UHFFFAOYAK |ChEMBL_Ref = |ChEMBL = 254348 |PubChem = 6890 |EC_number = 201-749-8 |UNII = FGQ8A78L14 |StdInChI_Ref = |StdInChI = 1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3 |StdInChIKey_Ref = |StdInChIKey = OCDGBSUVYYVKQZ-UHFFFAOYSA-N |CASNo_Ref = |CASNo = 87-52-5 |SMILES = c1cccc2c1c(c[nH]2)CN(C)C |Section2={{Chembox Properties |Formula = C11H14N2 |MolarMass = 174.24 g/mol |MeltingPtC = 138 to 139 |Section7={{Chembox Hazards | NFPA-H = 2 | NFPA-R = 0 | NFPA-F = 1}}

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.

Occurrence

Gramine has been found in the giant reed, Arundo donax, Hordeum, (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. In contrast to DMT, gramine does not have significant psychedelic-like behavioral effects in animals. The same is true of 5-methoxygramine (5-MeO-gramine), which failed to substitute for DOM in rodent drug discrimination tests.

Gramine has been found to act as an agonist of the adiponectin receptor 1 (AdipoR1).

The LD50 of gramine is 44.6 mg/ kg iv in mice and 62.9 mg/ kg iv in rats. 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.

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. There are numerous recent studies on the potential health benefits of Gramine.

References

References

  1. Corcuera, L. J.. (1993). "Biochemical Basis of the Resistance of the Barley to Aphids". [[Phytochemistry (journal).
  2. (1935). "Über die Alkaloide von ''Arundo Donax'' L.". [[Berichte der Deutschen Chemischen Gesellschaft]].
  3. (1959). "Indole Alkaloids of ''Acer saccharinum'' (the Silver Maple), ''Dictyoloma incanescens'', ''Piptadenia colubrina'', and ''Mimosa hostilis''". [[Journal of Organic Chemistry]].
  4. Cheeke, P. R.. (1989). "Toxicants of Plant Origin, Alkaloids". CRC Press.
  5. (1975). "Hallucinogenic Agents". Wright-Scientechnica.
  6. (January 1983). "DOM-stimulus generalization to LSD and other hallucinogenic indolealkylamines". Eur J Pharmacol.
  7. (2013). "Identification of adiponectin receptor agonist utilizing a fluorescence polarization based high throughput assay". PLOS ONE.
  8. Erspamer, V.. (1954). "Pharmacology of Indolealkylamines". Pharmacological Reviews.
  9. Corcuera, L. J.. (1984). "Effects of Indole Alkaloids from Gramineae on Aphids". Phytochemistry.
  10. "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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adiponectin-receptor-agonistsindole-alkaloidsdimethylamino-compoundsplant-toxins