Virodhamine: Information from Answers.com

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
SMILES	`CCCCC\C=C/C\C= C/C\C=C/C\C=C/CCCC(=O)OCCN`
Properties
Molecular formula	C₂₂H₃₇NO₂
Molar mass	347.53468
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 anandamide, but they were 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.

Cannabinoids

Plant cannabinoids

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 • N-Arachidonoyl dopamine (NADA) • Oleamide

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-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-229 • JWH-359 • L-759,633 • L-759,656 • Levonantradol • Nabazenil • Nabidrox (Canbisol) • Nabilone • Nabitan • Naboctate • O-806 • O-823 • O-1057 • O-1125 • O-1238 • O-2545 • O-2694 • Parahexyl • Perrottetinene • Pirnabine • THC-O-acetate • THC-O-phosphate

Nonclassical cannabinoids	CP 47,497 • CP 55,244 • CP 55,940 • HU-308 • Nonabine • SPA-229 • Tinabinol • 2-Isopropyl-5-methyl-1-(2,6-dihydroxy-4-nonylphenyl)cyclohex-1-ene

Aminoalkylindoles	AM-630 • AM-694 • AM-1241 • JWH-007 • JWH-015 • JWH-018 • JWH-073 • JWH-081 • JWH-122 • JWH-167 • JWH-200 • JWH-203 • JWH-210 • JWH-249 • JWH-250 • GW-405,833 (L-768,242) • Pravadoline • WIN 55,212-2

Aminoalkylpyrroles	JWH-030 • JWH-147 • JWH-307

Eicosanoids	AM-883 • Arachidonyl-2'-chloroethylamide • Arachidonylcyclopropylamide • Methanandamide • O-585 • O-689 • O-1812 • O-1860 • O-1861

Others	Abnormal cannabidiol • BAY 38-7271 • BAY 59-3074 • CB-13 • GW-842,166X • JWH-171 • O-1918 • O-2220 • Org 28611 • VSN-16

Endocannabinoid
activity enhancers

AM-404 • CAY-10401 • CAY-10402 • JZL184 • N-arachidonoyl-serotonin • O-1624 • PF-622 • PF-750 • URB-597 • URB-602 • URB-754

Cannabinoid receptor
antagonists and
inverse agonists

AM-251 • AM-281 • AM-630 • BML-190 • CAY-10508 • CB-25 • CB-52 • Drinabant • Ibipinabant • JTE-907 • LY-320,135 • MK-9470 • NESS-0327 • O-1184 • O-1248 • O-2050 • O-2654 • Org 27569 • Otenabant • Rimonabant • SR-144,528 • Surinabant • Taranabant • VCHSR

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

Thromboxanes (TX)

A₂ · B₂

Leukotrienes (LT)

Precursor	Arachidonic acid 5-hydroperoxide

Initial	A₄ · B₄

SRS-A	C₄ · D₄ · E₄

Nonclassic

Lipoxins (A₄, B₄) · Virodhamine

By function

bronchoconstriction (PGF_2α, TXA₂, LTC₄, LTD₄, LTE₄)

vasoconstriction (PGF_2α, TXA₂, TXB₂) · vasodilation (PGE₂, PGI₂, LTC₄, LTD₄, LTE₄)

platelets: induce (TXA₂) inhibit (PGD₂, PGI₂) · leukocytes: induce (TXA₂, LTB₄) inhibit (PGD₂, PGE₂)

labor stimulation: (PGE₂ (Dinoprostone), PGF_2α (Dinoprost))

see also enzymes

v • d • e Neurotransmitters

Amino Acids	1,4-Butanediol • Alanine • Aspartate • Cycloserine • DMG • GABA • GHB • Glutamate • Glycine • Hypotaurine • Kynurenic Acid (Transtorine) • NAAG (Spaglumic Acid) • NMG (Sarcosine) • Serine • Taurine • TMG (Betaine)

Endocannabinoids	2-AG • 2-AGE (Noladin Ether) • AEA (Anandamide) • NADA • OAE (Virodhamine) • Oleamide

Gasotransmitters	Carbon Monoxide • Hydrogen Sulfide • Nitric Oxide • Nitrous Oxide

Monoamines	Dopamine • Epinephrine (Adrenaline) • Melatonin • Norepinephrine (Noradrenaline) • Serotonin (5-HT)

Neuropeptides	See here for more details..

Purines	Adenosine • ADP • AMP • ATP

Trace Amines	3-ITA • 5-MeO-DMT • Bufotenin • DMT • NMT • Octopamine • Phenethylamine • Synephrine • Thyronamine • Tryptamine • Tyramine

Others	Acetylcholine • Histamine

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Virodhamine

See also

References