Gramine
{{chembox
|Verifiedfields = changed
|Watchedfields = changed
|verifiedrevid = 415511050
|Name = Gramine
|PIN = 1-(1H-Indol-3-yl)-N,N-dimethylmethanamine
|OtherNames = donaxine
|ImageFile_Ref = {{chemboximage|correct|??}}
|ImageFile = Gramine Structure.png
|ImageSize = 150px
|ImageName = Chemical structure of gramine
|Section1={{Chembox Identifiers
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID = 6625
|ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI = 28948
|KEGG_Ref = {{keggcite|correct|kegg}}
|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 = {{ebicite|correct|EBI}}
|ChEMBL = 254348
|PubChem = 6890
|EC_number = 201-749-8
|UNII = FGQ8A78L14
|StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|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 = {{stdinchicite|correct|chemspider}}
|StdInChIKey = OCDGBSUVYYVKQZ-UHFFFAOYSA-N
|CASNo_Ref = {{cascite|correct|??}}
|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.{{cite journal | author = Corcuera, L. J. | title = Biochemical Basis of the Resistance of the Barley to Aphids | journal = Phytochemistry | year = 1993 | volume = 33 | issue = 4 | pages = 741–747 | doi = 10.1016/0031-9422(93)85267-U}}
Occurrence
Gramine has been found in the giant reed, Arundo donax,{{cite journal | title = Über die Alkaloide von Arundo Donax L. |author1=Orechoff, A. |author2=Norkina, S. | journal = Berichte der Deutschen Chemischen Gesellschaft | year = 1935 | volume = 68 | issue = 3 | pages = 436–437 | doi = 10.1002/cber.19350680312}} Acer saccharinum (Silver Maple),{{cite journal |author1=Pachter, I. J. |author2=Zacharias, D. E. |author3=Ribeiro, O. | title = Indole Alkaloids of Acer saccharinum (the Silver Maple), Dictyoloma incanescens, Piptadenia colubrina, and Mimosa hostilis | journal = Journal of Organic Chemistry | year = 1959 | volume = 24 | issue = 9 | pages = 1285–1287 | doi = 10.1021/jo01091a032}} Hordeum, (a grass genus that includes barley) and Phalaris{{cite book | title = Toxicants of Plant Origin, Alkaloids | page = 172 | author = Cheeke, P. R. | publisher = CRC Press | year = 1989 | isbn = 0-8493-6990-8 | url = https://books.google.com/books?id=eASgQyXq8xMC&pg=PA172}} (another grass genus).
Effects and toxicity
Gramine has been found to act as an agonist of the adiponectin receptor 1 (AdipoR1).{{cite journal | vauthors = Sun Y, Zang Z, Zhong L, Wu M, Su Q, Gao X, Zan W, Lin D, Zhao Y, Zhang Z | title = Identification of adiponectin receptor agonist utilizing a fluorescence polarization based high throughput assay | journal = PLOS ONE | volume = 8 | issue = 5 | pages = e63354 | year = 2013 | pmid = 23691032 | pmc = 3653934 | doi = 10.1371/journal.pone.0063354| bibcode = 2013PLoSO...863354S | doi-access = free }}
The LD50 of gramine is 44.6 mg/ kg iv in mice and 62.9 mg/ kg iv in rats.{{cite journal | author = Erspamer, V. | title = Pharmacology of Indolealkylamines | journal = Pharmacological Reviews | year = 1954 | volume = 6 | issue = 4 | pages = 425–487 | doi = 10.1016/S0031-6997(25)07372-7 | pmid = 13236482 | url = http://pharmrev.aspetjournals.org/content/6/4/425.abstract}}
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.{{cite journal | author = Corcuera, L. J. | title = Effects of Indole Alkaloids from Gramineae on Aphids | journal = Phytochemistry | year = 1984 | volume = 23 | issue = 3 | pages = 539–541 | doi = 10.1016/S0031-9422(00)80376-3| bibcode = 1984PChem..23..539C }}
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. "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/ There are numerous recent studies on the potential health benefits of Gramine.
See also
- Dimethyltryptamine (DMT)