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Virodhamine

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]

Virodhamine
Names
Preferred IUPAC name
2-Aminoethyl (5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoate
Other names
O-Arachidonoyl ethanolamine
Identifiers
  • 287937-12-6 N
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL187349 Y
ChemSpider
  • 4650158 Y
ECHA InfoCard 100.158.921
  • 5554
  • 5712057
  • InChI=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- Y
    Key: DLHLOYYQQGSXCC-DOFZRALJSA-N Y
  • 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-
    Key: DLHLOYYQQGSXCC-DOFZRALJBB
  • O=C(OCCN)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
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).
N verify (what is YN ?)

See also edit

References edit

  1. ^ 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.


virodhamine, arachidonoyl, ethanolamine, endocannabinoid, nonclassic, eicosanoid, derived, from, arachidonic, acid, arachidonoyl, ethanolamine, arachidonic, acid, ethanolamine, joined, ester, linkage, opposite, amide, linkage, found, anandamide, based, this, o. 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 Virodhamine NamesPreferred IUPAC name 2 Aminoethyl 5Z 8Z 11Z 14Z icosa 5 8 11 14 tetraenoateOther names O Arachidonoyl ethanolamineIdentifiersCAS Number 287937 12 6 N3D model JSmol Interactive imageChEMBL ChEMBL187349 YChemSpider 4650158 YECHA InfoCard 100 158 921IUPHAR BPS 5554PubChem CID 5712057InChI InChI 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 YKey DLHLOYYQQGSXCC DOFZRALJSA N YInChI 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 Key DLHLOYYQQGSXCC DOFZRALJBBSMILES O C OCCN CCC C C C C C C C C C C C CCCCCPropertiesChemical formula C22H37NO2Molar mass 347 53468Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox referencesSee also editAnandamide OleamideReferences 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 nbsp This article about an alkene is a stub You can help Wikipedia by expanding it vte nbsp This biochemistry article is a stub You can help Wikipedia by expanding it vte nbsp This cannabinoid related article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Virodhamine amp oldid 1125085207, wikipedia, wiki, book, books, library,

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