Content deleted Content added
mNo edit summary |
Citation bot (talk | contribs) Add: s2cid. | Use this bot. Report bugs. | Suggested by Whoop whoop pull up | #UCB_webform 527/653 |
||
| (26 intermediate revisions by 20 users not shown) | |||
| Line 1: | Line 1: | ||
{{chembox |
{{chembox |
||
| Verifiedfields = changed |
|||
| verifiedrevid = |
| verifiedrevid = 470630951 |
||
| ImageFile = virodhamine. |
| ImageFile = virodhamine.svg |
||
| |
| PIN = 2-Aminoethyl (5''Z'',8''Z'',11''Z'',14''Z'')-icosa-5,8,11,14-tetraenoate |
||
| OtherNames= ''O''-Arachidonoyl ethanolamine |
| OtherNames= ''O''-Arachidonoyl ethanolamine |
||
| Section1 = {{Chembox Identifiers |
| Section1 = {{Chembox Identifiers |
||
| IUPHAR_ligand = 5554 |
|||
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
||
| ChemSpiderID = 4650158 |
| ChemSpiderID = 4650158 |
||
| InChI = 1/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(24)25-21-20-23/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21,23H2,1H3/b7-6-,10-9-,13-12-,16-15- |
| InChI = 1/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(24)25-21-20-23/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21,23H2,1H3/b7-6-,10-9-,13-12-,16-15- |
||
| InChIKey = DLHLOYYQQGSXCC-DOFZRALJBB |
| InChIKey = DLHLOYYQQGSXCC-DOFZRALJBB |
||
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
|||
| ChEMBL = 187349 |
|||
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
||
| StdInChI = 1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(24)25-21-20-23/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21,23H2,1H3/b7-6-,10-9-,13-12-,16-15- |
| StdInChI = 1S/C22H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(24)25-21-20-23/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21,23H2,1H3/b7-6-,10-9-,13-12-,16-15- |
||
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
||
| StdInChIKey = DLHLOYYQQGSXCC-DOFZRALJSA-N |
| StdInChIKey = DLHLOYYQQGSXCC-DOFZRALJSA-N |
||
| CASNo_Ref = {{cascite|changed|??}} |
|||
| CASNo = |
| CASNo = 287937-12-6 |
||
| PubChem = 5712057 |
| PubChem = 5712057 |
||
| SMILES = O=C(OCCN)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC |
| SMILES = O=C(OCCN)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC |
||
| Line 23: | Line 28: | ||
}} |
}} |
||
'''Virodhamine''' ('''''O''-arachidonoyl ethanolamine''') is an [[Cannabinoids|endocannabinoid]] and a nonclassic [[eicosanoid]], derived from [[arachidonic acid]]. ''O''-Arachidonoyl ethanolamine is [[arachidonic acid]] and [[ethanolamine]] joined by an [[ester]] linkage, the opposite of the [[amide]] linkage found in [[anandamide]]. Based on this opposite orientation, the molecule was named virodhamine from the Sanskrit word ''virodha'', which means opposition. It acts as an [[Receptor antagonist|antagonist]] of the [[Cannabinoid receptor|CB<sub>1</sub> receptor]] and [[agonist]] of the [[Cannabinoid_receptor#CB2|CB<sub>2</sub> receptor]]. Concentrations of virodhamine in the human hippocampus are similar to those of [[anandamide]], but they are 2- to 9-fold higher in peripheral tissues that express CB<sub>2</sub>. Virodhamine lowers body temperature in mice, demonstrating cannabinoid activity ''in vivo''.<ref name="pmid12023533">{{cite journal |
'''Virodhamine''' ('''''O''-arachidonoyl ethanolamine'''; '''O-AEA''') is an [[Cannabinoids|endocannabinoid]] and a nonclassic [[eicosanoid]], derived from [[arachidonic acid]]. ''O''-Arachidonoyl ethanolamine is [[arachidonic acid]] and [[ethanolamine]] joined by an [[ester]] linkage, the opposite of the [[amide]] linkage found in [[anandamide]]. Based on this opposite orientation, the molecule was named virodhamine from the [[Sanskrit]] word ''virodha'', which means opposition. It acts as an [[Receptor antagonist|antagonist]] of the [[Cannabinoid receptor|CB<sub>1</sub> receptor]] and [[agonist]] of the [[Cannabinoid_receptor#CB2|CB<sub>2</sub> receptor]]. Concentrations of virodhamine in the human hippocampus are similar to those of [[anandamide]], but they are 2- to 9-fold higher in peripheral tissues that express CB<sub>2</sub>. Virodhamine lowers body temperature in mice, demonstrating cannabinoid activity ''in vivo''.<ref name="pmid12023533">{{cite journal |
||
|author=Porter AC |
|author=Porter AC |
||
|title=Characterization of a novel endocannabinoid, virodhamine, with antagonist activity at the CB1 receptor |
|title=Characterization of a novel endocannabinoid, virodhamine, with antagonist activity at the CB1 receptor |
||
|journal=J. Pharmacol. Exp. Ther. |
|journal=J. Pharmacol. Exp. Ther. |
||
| Line 34: | Line 39: | ||
|pmid=12023533 |
|pmid=12023533 |
||
|doi=10.1124/jpet.301.3.1020 |
|doi=10.1124/jpet.301.3.1020 |
||
| |
|access-date=2007-10-31 |
||
|name-list-style=vanc|author2=Sauer JM |
|||
|author3=Knierman MD |
|||
|display-authors=3 |
|||
|last4=Becker |
|||
|first4=GW |
|||
|last5=Berna |
|||
|first5=MJ |
|||
|last6=Bao |
|||
|first6=J |
|||
|last7=Nomikos |
|||
|first7=GG |
|||
|last8=Carter |
|||
|first8=P |
|||
|last9=Bymaster |
|||
|first9=FP |
|||
|s2cid=26156181 |
|||
}}</ref> |
}}</ref> |
||
| Line 42: | Line 63: | ||
==References== |
==References== |
||
{{Reflist |
{{Reflist}} |
||
| Line 48: | Line 69: | ||
{{Eicosanoids}} |
{{Eicosanoids}} |
||
{{Neurotransmitters}} |
{{Neurotransmitters}} |
||
{{Cannabinoidergics}} |
|||
[[Category:Eicosanoids]] |
[[Category:Eicosanoids]] |
||
[[Category: |
[[Category:Endocannabinoids]] |
||
[[Category:Fatty acid esters]] |
|||
[[Category:CB1 receptor antagonists]] |
|||
[[Category:CB2 receptor agonists]] |
|||
{{alkene-stub}} |
|||
{{biochem-stub}} |
{{biochem-stub}} |
||
{{cannabinoid-stub}} |
{{cannabinoid-stub}} |
||
[[it:Virodamina]] |
|||
Latest revision as of 03:16, 2 December 2022
| |
| Names | |
|---|---|
| Preferred IUPAC name
2-Aminoethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate | |
| Other names
O-Arachidonoyl ethanolamine
| |
| Identifiers | |
3D model (JSmol)
|
|
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.158.921 |
PubChem CID
|
|
| |
| |
| Properties | |
| C22H37NO2 | |
| Molar mass | 347.53468 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Virodhamine (O-arachidonoyl ethanolamine; O-AEA) is an endocannabinoid and a nonclassic eicosanoid, derived from arachidonic acid. O-Arachidonoyl ethanolamine is arachidonic acid and ethanolamine joined by an ester linkage, the opposite of the amide linkage found in anandamide. Based on this opposite orientation, the molecule was named virodhamine from the Sanskrit word virodha, which means opposition. It acts as an antagonist of the CB1 receptor and agonist of the CB2 receptor. Concentrations of virodhamine in the human hippocampus are similar to those of anandamide, but they are 2- to 9-fold higher in peripheral tissues that express CB2. Virodhamine lowers body temperature in mice, demonstrating cannabinoid activity in vivo.[1]
See also[edit]
References[edit]
- ^ Porter AC, Sauer JM, Knierman MD, et al. (2002). "Characterization of a novel endocannabinoid, virodhamine, with antagonist activity at the CB1 receptor". J. Pharmacol. Exp. Ther. 301 (3): 1020–4. doi:10.1124/jpet.301.3.1020. PMID 12023533. S2CID 26156181. Retrieved 2007-10-31.