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Pravadoline

Pravadoline
Drug information
Systematic (IUPAC) name
IUPAC name(4-methoxyphenyl)-[2-methyl-1-(2-morpholin-4-ylethyl)indol-3-yl]methanone
Chemical data
Mol. mass378.46 g/mol
Therapeutic considerations
Legal status Legal

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Pravadoline (WIN 48,098) is an antiinflammatory and analgesic drug with an IC50 of 4.9 µM, related in structure to non-steroidal antinflammtory drugs (NSAIDs) such as indometacin. It was developed in the 1980s as a new antiinflammatory and prostaglandin synthesis inhibitor, acting through inhibition of the enzyme cyclooxygenase (COX).

However pravadoline was found to exhibit unexpectedly strong analgesic effects, which appeared at doses ten times smaller than the effective anti-inflammatory dose and so could not be explained by its action as a COX inhibitor. These effects were not blocked by opioid antagonists such as naloxone, and it was eventually discovered that pravadoline represented the first compound from a novel class of cannabinoid agonists, the aminoalkylindoles.

Pravadoline was never developed for use as an analgesic, partly due to toxicity concerns (although these were later shown to be a result of the salt form that the drug had been prepared in rather than from the pravadoline itself), however the discovery of cannabinoid activity in this structurally novel family of drugs led to the discovery of several new cannabinoid agonists, including the drug WIN 55,212-2 which is now widely used in scientific research.

Pravadoline Video

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0.77 min. | 5.0 user rating

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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 * 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-938 * AM-4030 * AMG-1 * AMG-3 * AMG-36 * AMG-41 * Dexanabinol (HU-211) * DMHP * Dronabinol * HHC * HU-210 * HU-243 * JWH-051 * JWH-133 * JWH-139 * JWH-229 * JWH-359 * L-759,633 * L-759,656 * Levonantradol (CP 50,5561) * 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
Benzoylindoles AM-630 * AM-694 * AM-1241 * GW-405,833 (L-768,242) * Pravadoline
Naphthoylindoles AM-1220 * JWH-007 * JWH-015 * JWH-018 * JWH-019 * JWH-073 * JWH-081 * JWH-122 * JWH-182 * JWH-200 * JWH-210 * JWH-398 * WIN 55,212-2
Phenylacetylindoles JWH-203 * JWH-250 * JWH-251 * JWH-302
Naphthoylpyrroles 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 A-836,339 * Abnormal cannabidiol * BAY 38-7271 * BAY 59-3074 * CB-13 * GW-842,166X * JWH-171 * O-1918 * O-2220 * Leelamine * Org 28611 * VSN-16
Endocannabinoid
activity enhancers
AM-404 * CAY-10401 * CAY-10402 * JZL184 * N-arachidonoyl-serotonin * O-1624 * PF-622 * PF-750 * PF-3845 * URB-597 * URB-602 * Genistein * Arvanil * Olvanil * Kaempferol * Biochanin A * URB-754 |
Cannabinoid receptor
antagonists and
inverse agonists
AM-251 * AM-281 * AM-630 * BML-190 * CAY-10508 * CB-25 * CB-52 * Drinabant * Hemopressin * 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 |



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