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Virodhamine

️Wed Oct 31 2007

Virodhamine

IUPAC name 2-aminoethyl (5Z,8Z,11Z,14Z)-icosa- 5,8,11,14-tetraenoate
Other names O-Arachidonoyl ethanolamine
Identifiers
CAS number	443129-35-9
PubChem	5712057
ChemSpider	4650158
ChEMBL	CHEMBL187349
Jmol-3D images	Image 1
SMILES O=C(OCCN)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC
InChI 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- Key: DLHLOYYQQGSXCC-DOFZRALJSA-N 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
Properties
Molecular formula	C₂₂H₃₇NO₂
Molar mass	347.53468
(verify) (what is: /?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Virodhamine (O-arachidonoyl ethanolamine) 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]

References

^ 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. http://jpet.aspetjournals.org/cgi/reprint/301/3/1020. Retrieved 2007-10-31.

v · d · eCannabinoids

Plant cannabinoids

Caryophyllene · CBCV · CBD · CBDV · CBGM · CBGV · CBN · CBG · CBV · CBL · THC · THC-C4 · THCV

Cannabinoid metabolites

8,11-DiOH-THC · 11-COOH-THC · 11-OH-THC

Endogenous cannabinoids

Arachidonoyl ethanolamide (Anandamide or AEA) · 2-Arachidonoylglycerol (2-AG) · 2-Arachidonyl glyceryl ether (noladin ether) · Virodhamine · Palmitoylethanolamide (PEA) · N-Arachidonoyl dopamine (NADA) · Oleamide · RVD-Hpα

Synthetic cannabinoid
receptor agonists

Classical cannabinoids (Dibenzopyrans)	A-40174 · A-41988 · A-42574 · Ajulemic acid · AM-087 · AM-411 · AM-855 · AM-905 · AM-906 · AM-919 · AM-926 · AM-938 · AM-4030 · AMG-1 · AMG-3 · AMG-36 · AMG-41 · Dexanabinol (HU-211) · DMHP · Dronabinol · HHC · HU-210 · JWH-051 · JWH-133 · JWH-139 · JWH-161 · JWH-229 · JWH-359 · KM-233 · L-759,633 · L-759,656 · Levonantradol (CP 50,5561) · Nabazenil · Nabidrox (Canbisol) · Nabilone · Nabitan · Naboctate · O-581 · O-774 · O-806 · O-823 · O-1057 · O-1125 · O-1238 · O-2365 · O-2372 · O-2373 · O-2383 · O-2426 · O-2484 · O-2545 · O-2694 · O-2715 · O-2716 · O-3223 · O-3226 · Parahexyl · Perrottetinene · Pirnabine · THC-O-acetate · THC-O-phosphate

Nonclassical cannabinoids	Cannabicyclohexanol · CP 47,497 · CP 55,244 · CP 55,940 · HU-308 · HU-320 · HU-331 · HU-336 · HU-345 · Nonabine · O-1376 · O-1422 · O-1601 · O-1656 · O-1657 · O-1660 · O-1871 · SPA-229 · Tinabinol · 2-Isopropyl-5-methyl-1-(2,6-dihydroxy-4-nonylphenyl)cyclohex-1-ene

Benzoylindoles	1-Butyl-3-(2-methoxybenzoyl)indole · 1-Butyl-3-(4-methoxybenzoyl)indole · 1-Pentyl-3-(2-methoxybenzoyl)indole · AM-630 · AM-679 · AM-694 · AM-1241 · AM-2233 · GW-405,833 (L-768,242) · Pravadoline · RCS-4 · WIN 54,461

Naphthoylindoles	AM-1220 · AM-1221 · AM-1235 · AM-2201 · AM-2232 · JWH-007 · JWH-015 · JWH-018 · JWH-019 · JWH-073 · JWH-081 · JWH-098 · JWH-116 · JWH-122 · JWH-149 · JWH-164 · JWH-182 · JWH-193 · JWH-198 · JWH-200 · JWH-210 · JWH-398 · JWH-424 · WIN 55,212-2

Naphthylmethylindoles	JWH-175 · JWH-184 · JWH-185 · JWH-192 · JWH-194 · JWH-195 · JWH-196 · JWH-197 · JWH-199

Phenylacetylindoles	Cannabipiperidiethanone · JWH-167 · JWH-203 · JWH-249 · JWH-250 · JWH-251 · JWH-302 · RCS-8

Naphthoylpyrroles	JWH-030 · JWH-147 · JWH-307 · JWH-370

Eicosanoids	AM-883 · Arachidonyl-2'-chloroethylamide (ACEA) · Arachidonylcyclopropylamide (ACPA) · Methanandamide (AM-356) · O-585 · O-689 · O-1812 · O-1860 · O-1861

Others	(1-Pentylindol-3-yl)-(2,2,3,3-tetramethylcyclopropyl)methanone · N-(S)-Fenchyl-1-(2-morpholinoethyl)-7-methoxyindole-3-carboxamide · A-796,260 · A-834,735 · A-836,339 · Abnormal cannabidiol · AB-001 · AM-1248 · AZ-11713908 · BAY 38-7271 · BAY 59-3074 · CB-13 · CB-86 · GW-842,166X · JWH-171 · JWH-176 · JTE 7-31 · Leelamine · MDA-19 · O-1918 · O-2220 · Org 28312 · Org 28611 · SER-601 · VSN-16 · WIN 56,098

Allosteric modulators of
cannabinoid receptors

Org 27569 · Org 27759 · Org 29647

Endocannabinoid
activity enhancers

AM-404 · CAY-10401 · CAY-10429 · JZL184 · JZL195 · Arachidonoyl serotonin · O-1624 · PF-04457845 · PF-622 · PF-750 · PF-3845 · PHOP · URB-447 · URB-597 · URB-602 · URB-754 · Genistein · Arvanil · Olvanil · Kaempferol · Biochanin A

Cannabinoid receptor
antagonists and
inverse agonists

AM-251 · AM-281 · AM-630 · BML-190 · CAY-10508 · CB-25 · CB-52 · CB-86 · Drinabant · Hemopressin · Ibipinabant (SLV319) · JTE-907 · LY-320,135 · Taranabant (MK-0364) · MK-9470 · NESS-0327 · O-1184 · O-1248 · O-2050 · O-2654 · Otenabant · Rimonabant (SR141716) · SR144528 · Surinabant (SR147778) · TM-38837 · VCHSR

v · Autacoids, unsaturated fatty acids: Eicosanoids

Precursor

Arachidonic acid

Prostanoids

Prostaglandins (PG) and
analogues

Precursor

H₂

Active

D/J	D₂

E/F	E₂ (Dinoprostone): Enprostil · Sulprostone E₁ (Alprostadil): Misoprostol · Gemeprost F_2α (Dinoprost): Bimatoprost · Carboprost · Latanoprost · Tafluprost · Travoprost · Unoprostone

I	I₂ (Prostacyclin/Epoprostenol): Beraprost · Iloprost · Treprostinil