Virodhamine
Names
Preferred IUPAC name
2-Aminoethyl (5Z ,8Z ,11Z ,14Z )-icosa-5,8,11,14-tetraenoate
Other names
O -Arachidonoyl ethanolamine
Identifiers
CAS Number
287937-12-6 N
3D model (JSmol )
ChEMBL
ChemSpider
ECHA InfoCard
100.158.921
IUPHAR/BPS
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
Chemical formula
C22 H37 NO2
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 (what is Y N ?)
Infobox references
Chemical compound
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 [ ]
References [ ]
Cannabinoids
Phytocannabinoids
Cannabichromenes Cannabicyclols Cannabidiols Cannabielsoins Cannabigerols Cannabinols and cannabinodiols Cannabitriols Delta-8-tetrahydrocannabinols Delta-9-tetrahydrocannabinols
Delta-9-THC (THC)
THCH
THCP
THCV
Miscellaneous cannabinoids Active metabolites
Endocannabinoids
Arachidonoyl ethanolamide (AEA; anandamide)
2-Arachidonoylglycerol (2-AG)
2-Arachidonyl glyceryl ether (2-AGE; noladin ether)
2-Oleoylglycerol (2-OG)
N-Arachidonoyl dopamine (NADA)
N-Arachidonylglycine (NAGly)
N-Arachidonoyl serotonin (AA-5-HT)
Docosatetraenoylethanolamide (DEA)
Lysophosphatidylinositol (LPI)
Oleamide
Oleoylethanolamide (OEA)
Palmitoylethanolamide (PEA)
RVD-Hpα
Stearoylethanolamide (SEA)
O-Arachidonoyl ethanolamine (O-AEA; virodhamine)
Synthetic cannabinoids
Classical cannabinoids (dibenzopyrans) Non-classical cannabinoids Adamantoylindoles Benzimidazoles Benzoylindoles
AM-630
AM-679
AM-694
AM-1241
AM-2233
GW-405,833 (L-768,242)
Pravadoline
RCS-4
WIN 54,461
Cyclohexylphenols Eicosanoids Hydrocarbons Indazole carboxamides Indazole-3- carboxamides Indole-3-carboxamides Indole-3-carboxylates Naphthoylindazoles Naphthoylindoles Naphthoylpyrroles Naphthylmethylindenes
AM-2201
AM-694
WIN-55,212-2
Naphthylmethylindoles Phenylacetylindoles Pyrazolecarboxamides Pyrrolobenzoxazines Quinolinyl esters Tetramethylcyclo- propanoylindazoles Tetramethylcyclo- propanoylindoles
A-796,260
A-834,735
FUB-144
UR-144
XLR-11
XLR-12
Tetramethylcyclo- propylindoles Others
Allosteric CBR ligands Endocannabinoid enhancers (inactivation inhibitors) Anticannabinoids (antagonists/inverse agonists/antibodies)
See also: Cannabinoid receptor modulators (cannabinoids by pharmacology)
List of: AM cannabinoids
JWH cannabinoids
Designer drugs § Synthetic cannabimimetics
Eicosanoids
Precursor Prostanoids
Prostaglandins (PG)
Precursor Active
D/J E /FI
I2 (Prostacyclin/Epoprostenol) :
Thromboxanes (TX)
Leukotrienes (LT)
Precursor
Arachidonic acid 5-hydroperoxide
Initial SRS-A
Eoxins (EX)
Nonclassic By function
vasoconstriction
vasodilation
platelets : induce
inhibit
leukocytes : induce
inhibit
labor stimulation:
PGE2 (Dinoprostone)
PGF2α (Dinoprost)
Neurotransmitters
Amino acid -derived
Major excitatory / inhibitory systems
Glutamate system
Agmatine
Aspartic acid (aspartate)
Glutamic acid (glutamate)
Glutathione
Glycine
GSNO
GSSG
Kynurenic acid
NAA
NAAG
Proline
Serine
GABA system Glycine system
α-Alanine
β-Alanine
Glycine
Hypotaurine
Proline
Sarcosine
Serine
Taurine
GHB system
Biogenic amines
Monoamines
6-OHM
Dopamine
Epinephrine (adrenaline)
NAS (normelatonin)
Norepinephrine (noradrenaline)
Serotonin (5-HT)
Trace amines
3-Iodothyronamine
N-Methylphenethylamine
N-Methyltryptamine
m -Octopamine
p -Octopamine
Phenylethanolamine
Phenethylamine
Synephrine
Tryptamine
m -Tyramine
p -Tyramine
Others
Neuropeptides
Lipid -derived
Endocannabinoids Neurosteroids
Nucleobase -derived
Vitamin -derived
Miscellaneous
Gasotransmitters
Carbon monoxide (CO)
Hydrogen sulfide (H2 S)
Nitric oxide (NO)
Candidates
Acetaldehyde
Ammonia (NH3 )
Carbonyl sulfide (COS)
Nitrous oxide (N2 O)
Sulfur dioxide (SO2 )
Receptor (ligands )
CB1
Agonists (abridged; see here for more) : 2-AG
2-AGE (noladin ether)
11-Hydroxy-THC
α-Amyrin · β-Amyrin
AB-CHMINACA
AM-1220
AM-1221
AM-1235
AM-2201
AM-2232
Anandamide
AZ-11713908
Cannabinol
CB-13
CP 47,497
CP 55,940
Dimethylheptylpyran
DEA
ECG
EGCG
Epicatechin
Gallocatechol (gallocatechin)
Honokiol
HU-210
JWH-007
JWH-015
JWH-018
JWH-073
Kavain
L-759,633
Levonantradol
Menabitan
Nabilone
Nabitan
NADA
O-1812
Oleamide
Pravadoline
Serinolamide A
THC (dronabinol)
UR-144
WIN 55,212-2
Yangonin
CB2
Agonists: 2-AG
2-AGE (noladin ether)
3,3'-Diindolylmethane
4-O-Methylhonokiol
α-Amyrin · β-Amyrin
A-796,260
A-834,735
A-836,339
AM-1221
AM-1235
AM-1241
AM-2232
Anandamide
AZ-11713908
Cannabinol
Caryophyllene
CB-13
CBS-0550
CP 55,940
GW-405,833 (L-768,242)
GW-842,166X
HU-308
JTE 7-31
JWH-007
JWH-015
JWH-018
JWH-133
L-759,633
L-759,656
Magnolol
MDA-19
Nabitan
NADA
Olorinab (APD-371)
PF-03550096
S-444,823
SER-601
Serinolamide A
UR-144
Tedalinab
THC (dronabinol)
THCV
Virodhamine
NAGly (GPR18 )
Agonists: Abnormal cannabidiol
ACPA
AM251
Anandamide
Cannabidiol
NADGly
THC (dronabinol)
O-1602
GPR55
Agonists: 2-AGE (noladin ether)
Abnormal cannabidiol
AM-251
CP 55,940
Lysophosphatidylinositol
O-1602
Oleoylethanolamide
Palmitoylethanolamide
THC (dronabinol)
GPR119 Unsorted
Transporter (modulators )
eCBTs
Inhibitors:
AM-404
Arachidonoyl serotonin
Cannabidiol
Guineensine
LY-2183240
Paracetamol (acetaminophen)
URB-597
VDM-11
Enzyme (modulators )
FAAH MAGL
Inhibitors:
IDFP
JZL-184
JZL-195
MAFP
URB-602
ABHD6 ABHD12
Inhibitors: Betulinic acid
Maslinic acid
MAFP
Oleanolic acid
Orlistat (tetrahydrolipstatin)
Ursolic acid
Others
Precursors: Phosphatidylethanolamine
NAPE
Diacylglycerol
Others: (directly potentiates activity of 2-AG at CB1 receptor)
(FAAH-like anandamide transporter inhibitor)
See also
Receptor/signaling modulators
Cannabinoids (cannabinoids by structure)