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{{chembox
{{chembox
| Verifiedfields = changed
|Verifiedfields = changed
| Watchedfields = changed
|Watchedfields = changed
| verifiedrevid = 415511050
|verifiedrevid = 415511050
| Name = Gramine
|Name = Gramine
|PIN = 1-(1''H''-Indol-3-yl)-''N'',''N''-dimethylmethanamine
| IUPACName = 3-(Dimethylaminomethyl)indole
| OtherNames = donaxine
|OtherNames = donaxine
| ImageFile_Ref = {{chemboximage|correct|??}}
|ImageFile_Ref = {{chemboximage|correct|??}}
| ImageFile = Gramine Structure.png
|ImageFile = Gramine Structure.png
<!-- | ImageSize = 150px -->
|ImageSize = 150px
| ImageName = Chemical structure of gramine
|ImageName = Chemical structure of gramine
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
|ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 6625
|ChemSpiderID = 6625
| ChEBI_Ref = {{ebicite|correct|EBI}}
|ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 28948
|ChEBI = 28948
| KEGG_Ref = {{keggcite|correct|kegg}}
|KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C08304
|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
|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
|InChIKey = OCDGBSUVYYVKQZ-UHFFFAOYAK
| ChEMBL_Ref = {{ebicite|correct|EBI}}
|ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 254348
|ChEMBL = 254348
| PubChem = 6890
|PubChem = 6890
| EC_number = 201-749-8
|EC_number = 201-749-8
| UNII = FGQ8A78L14
|UNII = FGQ8A78L14
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
|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
|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_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = OCDGBSUVYYVKQZ-UHFFFAOYSA-N
|StdInChIKey = OCDGBSUVYYVKQZ-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|??}}
|CASNo_Ref = {{cascite|correct|??}}
| CASNo = 87-52-5
|CASNo = 87-52-5
| SMILES = c1cccc2c1c(c[nH]2)CN(C)C
|SMILES = c1cccc2c1c(c[nH]2)CN(C)C
}}
}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
| Formula = C<sub>11</sub>H<sub>14</sub>N<sub>2</sub>
|Formula = C<sub>11</sub>H<sub>14</sub>N<sub>2</sub>
| MolarMass = 174.24 g/mol
|MolarMass = 174.24 g/mol
| MeltingPtC = 138 to 139
|MeltingPtC = 138 to 139
⚫
}}
| MeltingPt_notes =
⚫
}}
|Section7={{Chembox Hazards
|Section7={{Chembox Hazards
| NFPA-H = 2
| NFPA-H = 2
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}}
}}


'''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.<ref name=barley>{{cite journal | author = Corcuera, L. J. | title = Biochemical Basis of the Resistance of the Barley to Aphids | journal = [[Phytochemistry (journal)|Phytochemistry]] | year = 1993 | volume = 33 | issue = 4 | pages = 741–747 | doi = 10.1016/0031-9422(93)85267-U }}</ref>
'''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.<ref name=barley>{{cite journal | author = Corcuera, L. J. | title = Biochemical Basis of the Resistance of the Barley to Aphids | journal = [[Phytochemistry (journal)|Phytochemistry]] | year = 1993 | volume = 33 | issue = 4 | pages = 741–747 | doi = 10.1016/0031-9422(93)85267-U}}</ref>


==Occurrence==
==Occurrence==
Gramine has been found in the giant reed, ''[[Arundo donax]]'',<ref>{{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}}</ref><ref name=toxicants/>''[[Acer saccharinum]]'' ([[Silver Maple]]),<ref>{{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 }}</ref> ''[[Hordeum]]'',<ref name=barley/><ref name=toxicants/> (a grass genus that includes barley) and ''[[Phalaris (plant)|Phalaris]]''<ref name=toxicants>{{ 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 }}</ref>(another grass genus).
Gramine has been found in the giant reed, ''[[Arundo donax]]'',<ref>{{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}}</ref><ref name=toxicants/> ''[[Acer saccharinum]]'' ([[Silver Maple]]),<ref>{{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}}</ref> ''[[Hordeum]]'',<ref name=barley/><ref name=toxicants/> (a grass genus that includes barley) and ''[[Phalaris (plant)|Phalaris]]''<ref name=toxicants>{{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}}</ref> (another grass genus).


==Effects and toxicity==
==Effects and toxicity==
Gramine has been found to act as an [[agonist]] of the [[adiponectin receptor 1]] (AdipoR1).<ref name="pmid23691032">{{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 | url = }}</ref>
Gramine has been found to act as an [[agonist]] of the [[adiponectin receptor 1]] (AdipoR1).<ref name="pmid23691032">{{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 }}</ref>


The LD50 of gramine is 44.6&nbsp;mg/ kg iv in mice and 62.9&nbsp;mg/ kg iv in rats.<ref>{{ cite journal | author = Erspamer, V. | title = Pharmacology of Indolealkylamines | journal = Pharmacological Reviews | year = 1954 | volume = 6 | issue = 4 | pages = 425–487 | pmid = 13236482 | url = http://pharmrev.aspetjournals.org/content/6/4/425.abstract }}</ref>
The LD50 of gramine is 44.6&nbsp;mg/ kg iv in mice and 62.9&nbsp;mg/ kg iv in rats.<ref>{{cite journal | author = Erspamer, V. | title = Pharmacology of Indolealkylamines | journal = Pharmacological Reviews | year = 1954 | volume = 6 | issue = 4 | pages = 425–487 | pmid = 13236482 | url = http://pharmrev.aspetjournals.org/content/6/4/425.abstract}}</ref>
Numerous studies have been done on the toxicity in insects harmful to crops for use as a possible insecticide.<ref>{{ 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 }}</ref>
Numerous studies have been done on the toxicity of gramine to insects harmful to crops in order to assess its potential use as an insecticide.<ref>{{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}}</ref>


==References==
==References==
{{Reflist}}
{{Reflist}}

{{Signaling peptide/protein receptor modulators}}


[[Category:Adiponectin receptor agonists]]
[[Category:Adiponectin receptor agonists]]
[[Category:Indole alkaloids]]
[[Category:Indole alkaloids]]
[[Category:Amines]]
[[Category:Dimethylamino compounds]]
[[Category:Plant toxins]]

Latest revision as of 13:25, 22 December 2023

Gramine
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 Edit this at Wikidata
EC Number
  • 201-749-8
KEGG
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 checkY
    Key: OCDGBSUVYYVKQZ-UHFFFAOYSA-N checkY
  • 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 four-colored diamondHealth 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).
☒N verify (what is checkY☒N ?)

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

[edit]

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

[edit]

Gramine has been found to act as an agonist of the adiponectin receptor 1 (AdipoR1).[5]

The LD50 of gramine is 44.6 mg/ kg iv in mice and 62.9 mg/ kg iv in rats.[6] Numerous studies have been done on the toxicity of gramine to insects harmful to crops in order to assess its potential use as an insecticide.[7]

References

[edit]
  1. ^ a b 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. ^ a b c 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. ^ 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.
  6. ^ Erspamer, V. (1954). "Pharmacology of Indolealkylamines". Pharmacological Reviews. 6 (4): 425–487. PMID 13236482.
  7. ^ 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.
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