O-1812
Chemical compound
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Formula | C26H42N2O2 |
Molar mass | 414.634 g·mol−1 |
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O-1812 is an eicosanoid derivative related to anandamide that acts as a potent and highly selective agonist for the cannabinoid receptor CB1, with a Ki of 3.4 nM at CB1 and 3870 nM at CB2.[1] Unlike most related compounds, O-1812 is metabolically stable against rapid breakdown by enzymes, and produces a cannabinoid-like discriminative effect in rats, which is similar but not identical to that produced by cannabinoid drugs of other chemical classes.[2][3][4][5]
See also
References
- ^ Di Marzo V, et al. (February 2001). "Highly selective CB1 cannabinoid receptor ligands and novel CB1/VR1 vanilloid receptor "hybrid" ligands". Biochemical and Biophysical Research Communications. 281 (2): 444–51. doi:10.1006/bbrc.2001.4354. PMID 11181068.
- ^ Baskfield CY, Martin BR, Wiley JL (April 2004). "Differential effects of Δ9-tetrahydrocannabinol and methanandamide in CB1 knockout and wild-type mice". The Journal of Pharmacology and Experimental Therapeutics. 309 (1): 86–91. doi:10.1124/jpet.103.055376. PMID 14718593. S2CID 36621393.
- ^ Wiley JL, et al. (August 2004). "A comparison of the discriminative stimulus effects of Δ9-tetrahydrocannabinol and O-1812, a potent and metabolically stable anandamide analog, in rats". Experimental and Clinical Psychopharmacology. 12 (3): 173–9. doi:10.1037/1064-1297.12.3.173. PMID 15301634.
- ^ Wiley JL, Smith FL, Razdan RK, Dewey WL (March 2005). "Task specificity of cross-tolerance between Δ9-tetrahydrocannabinol and anandamide analogs in mice". European Journal of Pharmacology. 510 (1–2): 59–68. doi:10.1016/j.ejphar.2005.01.006. PMID 15740725.
- ^ Breivogel CS, et al. (July 2008). "Sensitivity to Δ9-tetrahydrocannabinol is selectively enhanced in β-arrestin2 -/- mice". Behavioural Pharmacology. 19 (4): 298–307. doi:10.1097/FBP.0b013e328308f1e6. PMC 2751575. PMID 18622177.
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(comparison)
Cannabibutols |
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Cannabichromenes | |
Cannabicyclols |
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Cannabidiols | |
Cannabielsoins |
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Cannabigerols | |
Cannabiphorols |
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Cannabinols | |
Cannabitriols |
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Cannabivarins |
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Delta-8-tetrahydrocannabinols |
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Delta-9-tetrahydrocannabinols | |
Delta-10-Tetrahydrocannabinols | |
Miscellaneous cannabinoids |
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Active metabolites |
- 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)
- 2-Arachidonoyl lysophosphatidylinositol (2-ALPI)
- 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)
cannabinoid
receptor
agonists /
neocannabinoids
Classical cannabinoids (dibenzopyrans) |
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Non-classical cannabinoids |
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Adamantoylindoles |
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Benzimidazoles | |
Benzoylindoles |
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Cyclohexylphenols | |
Eicosanoids |
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Hydrocarbons | |
Indazole carboxamides | |
Indazole-3- carboxamides |
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Indole-3-carboxamides |
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Indole-3-carboxylates | |
Naphthoylindazoles | |
Naphthoylindoles |
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Naphthoylpyrroles | |
Naphthylmethylindenes | |
Naphthylmethylindoles | |
Phenylacetylindoles | |
Pyrazolecarboxamides |
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Pyrrolobenzoxazines | |
Quinolinyl esters | |
Tetramethylcyclo- propanoylindazoles | |
Tetramethylcyclo- propanoylindoles | |
Tetramethylcyclo- propylindoles | |
Others |
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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 (OEA)
- Olvanil
- Palmitoylethanolamide (PEA)
- PF-04457845
- PF-622
- PF-750
- PF-3845
- PHOP
- URB-447
- URB-597
- URB-602
- URB-754
- VDM-11
(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 (AVE1625)
- Hemopressin
- 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 (CP-945,598)
- PF-514273
- PipISB
- PSB-SB-487
- Rimonabant (SR141716)
- Rosonabant (E-6776)
- SR-144,528
- Surinabant (SR147778)
- Taranabant (MK-0364)
- TM-38837
- VCHSR
- See also: Cannabinoid receptor modulators (cannabinoids by pharmacology)
- List of: AM cannabinoids
- JWH cannabinoids
- Designer drugs § Synthetic cannabimimetics
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