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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
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
Virodhamine
lowers body temperature in mice, demonstrating cannabinoid activity in vivo.[1] See also[edit]

Anandamide Oleamide

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. Retrieved 2007-10-31. 

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Cannabinoids

Phytocannabinoids

Alkylamides Caryophyllene CBC CBCV CBD CBDV CBG CBGM CBGV CBL CBDL CBN CBV Epigallocatechin gallate Gallocatechol Perrottetinene Serinolamide A THC THC-C4 THCA THCV Yangonin

Active metabolites: 8,11-DiOH-THC 11-COOH-THC 11-OH-THC

Endocannabinoids

Arachidonoyl ethanolamide (AEA; anandamide) 2-Arachidonoylglycerol
2-Arachidonoylglycerol
(2-AG) 2-Arachidonyl glyceryl ether
2-Arachidonyl glyceryl ether
(2-AGE; noladin ether) 2-Oleoylglycerol
2-Oleoylglycerol
(2-OG) N-Arachidonoyl dopamine
N-Arachidonoyl dopamine
(NADA) N-Arachidonylglycine
N-Arachidonylglycine
(NAGly) 2-Arachidonoyl lysophosphatidylinositol (2-ALPI) N- Arachidonoyl serotonin
Arachidonoyl serotonin
(AA-5-HT) Docosatetraenoylethanolamide
Docosatetraenoylethanolamide
(DEA) Lysophosphatidylinositol
Lysophosphatidylinositol
(LPI) Oleamide Oleoylethanolamide
Oleoylethanolamide
(OEA) Palmitoylethanolamide
Palmitoylethanolamide
(PEA) RVD-Hpα Stearoylethanolamide (SEA) O-Arachidonoyl ethanolamine (O-AEA; virodhamine)

Synthetic cannabinoids

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-2389 AM-4030 AMG-1 AMG-3 AMG-36 AMG-41 Dexanabinol
Dexanabinol
(HU-211) DMHP Dronabinol HHC HU-210 HU-243 JWH-051 JWH-133 JWH-139 JWH-161 JWH-229 JWH-359 KM-233 L-759,633 L-759,656 Levonantradol
Levonantradol
(CP 50,5561) Menabitan Nabazenil Nabidrox (Canbisol) Nabilone Nabitan Naboctate O-224 O-581 O-774 O-806 O-823 O-1057 O-1125 O-1191 O-1238 O-2048 O-2113 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 Pirnabine THC-O-acetate THC-O-phosphate

Non-classical cannabinoids

Cannabicyclohexanol CBD-DMH CP 47,497 (C6)-CP 47,497 (C9)-CP 47,497 CP 55,244 CP 55,940 HU-308 HU-320 HU-331 HU-336 HU-345 HU-446 HU-465 HU-910 HUF-101 Nonabine O-1376 O-1422 O-1601 O-1656 O-1657 O-1660 O-1663 O-1871 SPA-229 Tinabinol

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
GW-405,833
(L-768,242) Pravadoline RCS-4 WIN 54,461

Naphthoylindoles

AM-1220 AM-1221 AM-1235 AM-2201 AM-2232 CHM-081 EAM-2201 FUB-JWH-018 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 MAM-1220 MAM-2201 NE-CHMIMO

Naphthoylindazoles

THJ-018 THJ-2201

Pyrrolobenzoxazines

WIN 55,212-2

Naphthylmethylindoles

JWH-175 JWH-176 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

Indole-3-carboxamides

5F-ADBICA 5F-NNE1 5F-PCN 5F-SDB-006 AB-FUBICA AB-PICA ADBICA ADB-FUBICA APICA CUMYL-BICA CUMYL-PICA CUMYL-5F-PICA FDU-NNE1 MDMB-CHMICA MMB-2201 MN-25
MN-25
(UR-12) NNE1 PX-1 Org 28312 Org 28611 SDB-006 STS-135

Indole-3-carboxylates

5F-PB-22 FDU-PB-22 FUB-PB-22 QUCHIC
QUCHIC
(BB-22) QUPIC
QUPIC
(PB-22) NM-2201

Tetramethylcyclo- propanoylindoles

5Br-UR-144 5Cl-UR-144 A-796,260 A-834,735 FUB-144 UR-144 XLR-11 XLR-12

Indazole-3- carboxamides

5Cl-APINACA 5F-ADB 5F-ADB-PINACA 5F-AMB 5F-APINACA 5F-CUMYL-PINACA 5F-EMB-PINACA AB-CHMINACA AB-FUBINACA AB-FUBINACA
AB-FUBINACA
2-fluorobenzyl isomer AB-PINACA ADB-CHMINACA ADB-FUBINACA ADB-PINACA ADAMANTYL-THPINACA ADSB-FUB-187 AMB-CHMINACA AMB-FUBINACA APINACA
APINACA
(AKB48) APP-FUBINACA CUMYL-4CN-BINACA CUMYL-PINACA CUMYL-THPINACA EMB-FUBINACA FUB-APINACA MDMB-FUBINACA MDMB-CHMINACA MN-18 PX-2 PX-3

Tetramethylcyclo- propanoylindazoles

FAB-144

Naphthoylpyrroles

JWH-030 JWH-147 JWH-307 JWH-369 JWH-370

Eicosanoids

AM-883 AM-1346 ACEA ACPA Methanandamide
Methanandamide
(AM-356) O-585 O-689 O-1812 O-1860 O-1861

Pyrazolecarboxamides

5F-AB-FUPPYCA AB-CHFUPYCA AB-CHMFUPPYCA

Others

4-HTMPIPO 5F-PY-PICA 5F-PY-PINACA 5F-3-pyridinoylindole A-836,339 A-955,840 Abnormal cannabidiol AB-001 BzODZ-EPyr AM-1248 AM-1714 AZ-11713908 BAY 38-7271 BAY 59-3074 BIM-018 CB-13 CB-86 CBS-0550 CUMYL-4CN-B7AICA CUMYL-5F-P7AICA CUMYL-PEGACLONE FUBIMINA GSK-554,418A GW-842,166X JTE 7-31 LASSBio-881 LBP-1 Leelamine MDA-7 MDA-19 MEPIRAPIM NESS-040C5 NMP-7 O-889 O-1269 O-1270 O-1399 O-1602 O-2220 PF-03550096 PSB-SB-1202 PTI-1 PTI-2 QMPSB S-444,823 SER-601 Tedalinab URB-447 VSN-16 WIN 56,098

Allosteric CBR ligands

Org 27569 Org 27759 Org 29647 RTI-371 Pregnenolone

Endocannabinoid enhancers (inactivation inhibitors)

4-Nonylphenylboronic acid AM-404 Arachidonoyl serotonin Arvanil BIA 10-2474 Biochanin A CAY-10401 CAY-10429 Genistein Guineesine IDFP JNJ 1661010 JNJ-42165279 JZL184 JZL195 Kaempferol LY-2183240 MK-4409 O-1624 O-2093 Oleoylethanolamide
Oleoylethanolamide
(OEA) Olvanil Palmitoylethanolamide
Palmitoylethanolamide
(PEA) PF-04457845 PF-622 PF-750 PF-3845 PHOP URB-447 URB-597 URB-602 URB-754 VDM-11

Anticannabinoids (antagonists/inverse agonists/antibodies)

AM-251 AM-281 AM-630 AM-1387 AM-4113 AM-6527 AM-6545 BML-190 Brizantin (Бризантин) CAY-10508 CB-25 CB-52 CB-86 Dietressa (Диетресса) Drinabant
Drinabant
(AVE1625) Hemopressin Ibipinabant
Ibipinabant
(SLV319) JTE-907 LH-21 LY-320,135 MDA-77 MJ-15 MK-9470 NESS-0327 NIDA-41020 O-606 O-1184 O-1248 O-1918 O-2050 O-2654 Otenabant
Otenabant
(CP-945,598) PF-514273 PipISB PSB-SB-487 Rimonabant
Rimonabant
(SR141716) Rosonabant
Rosonabant
(E-6776) SR-144,528 Surinabant
Surinabant
(SR147778) Taranabant
Taranabant
(MK-0364) TM-38837 VCHSR

See also: Cannabinoid receptor
Cannabinoid receptor
modulators (cannabinoids by pharmacology) List of: AM cannabinoids JWH cannabinoids Designer drugs § Synthetic cannabimimetics

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Eicosanoids

Precursor

Arachidonic acid

Prostanoids

Prostaglandins (PG)

Precursor

H2

Active

D/J

D2

E/F

E2 (Dinoprostone)

E1 (Alprostadil)

F2α (Dinoprost):

I

I2 (Prostacyclin/Epoprostenol):

Thromboxanes (TX)

A2 B2

Leukotrienes (LT)

Precursor

Arachidonic acid
Arachidonic acid
5-hydroperoxide

Initial

A4 B4

SRS-A

C4 D4 E4

Eoxins (EX)

Precursor

Arachidonic acid
Arachidonic acid
15-hydroperoxide

Eoxins

A4 C4 D4 E4

Nonclassic

Lipoxins (LX) (A4, B4) Virodhamine

By function

bronchoconstriction

PGD2 TXA2 LTC4 LTD4 LTE4

vasoconstriction

PGF2α TXA2 TXB2)

vasodilation

PGE2 PGI2 LTC4 LTD4 LTE4

platelets: induce

TXA2

inhibit

PGD2 PGI2

leukocytes: induce

TXA2 LTB4

inhibit

PGD2 PGE2

fever stimulation:

PGE2

labor stimulation:

PGE2 (Dinoprostone) PGF2α (Dinoprost)

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Neurotransmitters

Amino acid-derived

Major excitatory/inhibitory systems: Glutamate system: Agmatine Aspartic acid
Aspartic acid
(aspartate) Cycloserine Glutamic acid
Glutamic acid
(glutamate) Glutathione Glycine GSNO GSSG Kynurenic acid NAA NAAG Proline Serine; GABA system: GABA GABOB GHB; Glycine
Glycine
system: α-Alanine β-Alanine Glycine Hypotaurine Proline Sarcosine Serine Taurine; GHB system: GHB T-HCA (GHC)

Biogenic amines: Monoamines: 6-OHM Dopamine Epinephrine
Epinephrine
(adrenaline) NAS (normelatonin) Norepinephrine
Norepinephrine
(noradrenaline) Serotonin
Serotonin
(5-HT); Trace amines: 3-Iodothyronamine N-Methylphenethylamine N-Methyltryptamine m-Octopamine p-Octopamine Phenylethanolamine Phenethylamine Synephrine Tryptamine m-Tyramine p-Tyramine; Others: Histamine

Neuropeptides: See here instead.

Lipid-derived

Endocannabinoids: 2-AG 2-AGE (noladin ether) 2-ALPI 2-OG AA-5-HT Anandamide
Anandamide
(AEA) DEA LPI NADA NAGly OEA Oleamide PEA RVD-Hpα SEA Virodhamine
Virodhamine
(O-AEA)

Neurosteroids: See here instead.

Nucleobase-derived

Nucleosides: Adenosine
Adenosine
system: Adenosine ADP AMP ATP

Vitamin-derived

Cholinergic system: Acetylcholine

Miscellaneous

Gasotransmitters: Carbon monoxide
Carbon monoxide
(CO) Hydrogen sulfide
Hydrogen sulfide
(H2S) Nitric oxide
Nitric oxide
(NO); Candidates: Acetaldehyde Ammonia
Ammonia
(NH3) Carbonyl sulfide
Carbonyl sulfide
(COS) Nitrous oxide
Nitrous oxide
(N2O) Sulfur dioxide
Sulfur dioxide
(SO2)

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Cannabinoid receptor
Cannabinoid receptor
modulators

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-1172 AM-1220 AM-1221 AM-1235 AM-2201 AM-2232 Anandamide Arvanil AZ-11713908 Cannabinol CB-13 CP 47,497 CP 55,940 Dimethylheptylpyran DEA ECG EGCG Epicatechin Gallocatechol
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

Antagonists: AM-251 AM-6545 Cannabidiol Cannabigerol Drinabant Falcarinol
Falcarinol
(carotatoxin) Hemopressin Ibipinabant LY-320,135 MK-9470 NESS-0327 O-2050 Otenabant PF-514273 PipISB Rimonabant Rosonabant Surinabant Taranabant THCV TM-38837 VCHSR Virodhamine

Antibodies: Brizantin (Бризантин) Dietressa (Диетресса)

Unknown/unsorted: MAFP

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-1172 AM-1221 AM-1235 AM-1241 AM-2232 Anandamide AZ-11713908 Cannabinol Caryophyllene CB-13 CBS-0550 CP-55,940 GW-405,833
GW-405,833
(L-768,242) GW-842,166X HU-308 JTE 7-31 JWH-007 JWH-015 JWH-018 JWH-73 JWH-133 L-759,633 L-759,656 Magnolol MDA-19 Nabitan NADA PF-03550096 S-444,823 SER-601 Serinolamide A UR-144 Tedalinab THC (dronabinol) THCV Tetrahydromagnolol Virodhamine

Antagonists: 4-O-Methylhonokiol AM-630 BML-190 Cannabidiol Honokiol JTE-907 SR-144,528 WIN 54,461 WIN 56,098

NAGly (GPR18)

Agonists: Abnormal cannabidiol ACPA AM251 Anandamide Cannabidiol NADGly THC (dronabinol) O-1602

Antagonists: CID-85469571 O-1918

GPR55

Agonists: 2-AGE (noladin ether) 2-ALPI Abnormal cannabidiol AM-251 CID1011163 CID1252842 CID1792579 CP 55,940 GSK-494581A Lysophosphatidylinositol ML-184 ML-185 ML-186 O-1602 Oleoylethanolamide Palmitoylethanolamide THC (dronabinol)

Antagonists: Cannabidiol CID-16020046 ML-191 ML-192 ML-193 O-1918 PSB-SB-487 PSB-SB-1202 PSB-SB-1203 Tetrahydromagnolol

GPR119

Agonists: 2-Oleoylglycerol Anandamide APD668 AR-231,453 AS-1269574 MBX-2982 N-Oleoyldopamine Oleoylethanolamide Olvanil PSN-375,963 PSN-632,408

Transporter (modulators)

eCBTs

Inhibitors: 5'-DMH-CBD AM-404 AM-1172 Arachidonoyl serotonin Arvanil Cannabidiol Guineensine LY-2183240 O-2093 OMDM-2 Paracetamol
Paracetamol
(acetaminophen) SB-FI-26 UCM-707 URB-597 VDM-11 WOBE490 WOBE491 WOBE492

Enzyme (modulators)

FAAH

Inhibitors: 4-Nonylphenylboronic acid AACOCF3 AM-404 Arachidonoyl serotonin BIA 10-2474 Biochanin A Genistein IDFP JNJ-1661010 JNJ-42165279 JZL-195 Kaempferol LY-2183240 MAFP Palmitoylisopropylamide Paracetamol
Paracetamol
(acetaminophen) PF-3845 PF-04457845 PF-750 SA-47 SA-57 TAK 21d TC-F 2 UCM710 URB-597

Activators: PDP-EA

MAGL

Inhibitors: ABX-1431 IDFP JJKK 048 JW 642 JZL-184 JZL-195 JZP-361 KML 29 MAFP MJN110 NAM Pristimerin URB-602

ABHD6

Inhibitors: JZP-169 JZP-430 KT182 KT185 KT195 KT203 LEI-106 ML294 ML295 ML296 UCM710 WWL-70

ABHD12

Inhibitors: Betulinic acid Maslinic acid MAFP Oleanolic acid Orlistat
Orlistat
(tetrahydrolipstatin) Ursolic acid

Others

Precursors: Phosphatidylethanolamine NAPE Diacylglycerol

Others: 2-PG (directly potentiates activity of 2-AG at CB1 receptor) ARN-272 (FAAH-like anandamide transporter inhibitor)

See also Receptor/signaling modulators Cannabinoids
Cannabinoids
(cannabinoids by structure)

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