Gramine

Last updated
Gramine
Chemical structure of gramine Gramine.svg
Chemical structure of gramine
Names
Preferred IUPAC name
1-(1H-Indol-3-yl)-N,N-dimethylmethanamine
Other names
donaxine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.001.591 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-749-8
KEGG
PubChem CID
UNII
  • InChI=1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3 Yes check.svgY
    Key: OCDGBSUVYYVKQZ-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3
    Key: OCDGBSUVYYVKQZ-UHFFFAOYAK
  • c1cccc2c1c(c[nH]2)CN(C)C
Properties
C11H14N2
Molar mass 174.24 g/mol
Melting point 138 to 139 °C (280 to 282 °F; 411 to 412 K)
Hazards
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
1
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Contents

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

References

  1. 1 2 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.
  2. ↑ 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. 1 2 3 Cheeke, P. R. (1989). Toxicants of Plant Origin, Alkaloids. CRC Press. p. 172. ISBN   0-8493-6990-8.
  4. ↑ 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. 1 2 Brimblecombe RW, Pinder RM (1975). "Indolealkylamines and Related Compounds". Hallucinogenic Agents. Bristol: Wright-Scientechnica. pp. 98–144. ISBN   978-0-85608-011-1. OCLC   2176880. OL   4850660M. 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).
  6. ↑ Glennon RA, Young R, Jacyno JM, Slusher M, Rosecrans JA (January 1983). "DOM-stimulus generalization to LSD and other hallucinogenic indolealkylamines". Eur J Pharmacol. 86 (3–4): 453–459. doi:10.1016/0014-2999(83)90196-6. PMID   6572591.
  7. ↑ Sun Y, Zang Z, Zhong L, Wu M, Su Q, Gao X, Zan W, Lin D, Zhao Y, Zhang Z (2013). "Identification of adiponectin receptor agonist utilizing a fluorescence polarization based high throughput assay". PLOS ONE. 8 (5): e63354. Bibcode:2013PLoSO...863354S. doi: 10.1371/journal.pone.0063354 . PMC   3653934 . PMID   23691032.
  8. ↑ Erspamer, V. (1954). "Pharmacology of Indolealkylamines" . Pharmacological Reviews. 6 (4): 425–487. doi:10.1016/S0031-6997(25)07372-7. PMID   13236482.
  9. ↑ Corcuera, L. J. (1984). "Effects of Indole Alkaloids from Gramineae on Aphids". Phytochemistry. 23 (3): 539–541. Bibcode:1984PChem..23..539C. doi:10.1016/S0031-9422(00)80376-3.
  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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