List of AM cannabinoids

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Alexandros Makriyannis is a professor in the Department of Medicinal Chemistry at Northeastern University, where his research group has synthesized many new compounds with cannabinoid activity. Some of those are:

  • AM-087 — an analgesic CB1 agonist derived from Δ8THC substituted with a side chain on the 3-position, it has a Ki of 0.43nM making it roughly 100x as potent as THC.
  • AM-251 — an inverse agonist at the CB1 cannabinoid receptor that is structurally related to SR141716A (rimonabant), but has a higher binding affinity with a Ki value of 7.5nM.[1]
  • AM-279 — a Schedule I substance in Alabama.[2]
  • AM-281 — N-(morpholin-4-yl)-1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-1H-pyrazole-3-carboxamide[1]
  • AM-356 — a synthetically created stable chiral analog of anandamide, it acts on the cannabinoid receptors with a Ki of 17.9nM at CB1 and 868nM at CB2.[3]
  • AM-374 — palmitylsulfonyl fluoride[4]
  • AM-381 — stearylsulfonyl fluoride
  • AM-404 — an active metabolite of paracetamol (acetaminophen) and a likely inhibitor of fatty acid amide hydrolase (FAAH)
  • AM-411 — an adamantyl-substituted derivative of Δ8THC, it is a potent and fairly selective CB1 full agonist with a Ki of 6.80nM. It is also a moderately potent CB2 agonist with a Ki of 52.0nM.
  • AM-630 — a potent and selective inverse agonist for the cannabinoid receptor CB2, with a Ki of 32.1nM at CB2 and 165x selectivity over CB1, at which it acts as a weak partial agonist.
  • AM-661 — 1-(N-methyl-2-piperidine)methyl-2-methyl-3-(2-iodo)benzoylindole[5]
  • AM-678 — another name for JWH-018, it is a full agonist at both cannabinoid receptors with some selectivity for CB2.
  • AM-679 — an iodobenzoylindole which acts as a moderately potent agonist for the cannabinoid receptors, with a Ki of 13.5nM at CB1 and 49.5nM at CB2.
  • AM-694 — an iodobenzoylindole which acts as a potent and selective agonist for the CB1 cannabinoid receptor, with a Ki of 0.08nM at CB1 and 18x selectivity over the related CB2 receptor (1.44nM).[6]
  • AM-735 — 3-bornyl-Δ8-THC, a mixed CB1 / CB2 agonist with Ki of 8.9nM at CB1 and 7.4nM at CB2.[7]
  • AM-855 — an analgesic derivative of Δ8tetrahydrocannabinol, it is an agonist at both CB1 and CB2 with moderate selectivity for CB1, with a Ki of 22.3nM at CB1 and 58.6nM at CB2.
  • AM-881 — a chlorine-substituted stereoisomer of anandamide whose Ki = 5.3nM at CB1 and 95nM at CB2.[3]
  • AM-883 — an allyl-substituted stereoisomer of anandamide whose Ki = 9.9nM at CB1 and 226nM at CB2.[3]
  • AM-905 — a potent and reasonably selective agonist for the CB1 cannabinoid receptor, with a Ki of 1.2nM at CB1 and 5.3nM at CB2.
  • AM-906 — a potent and dodecally selective agonist for the CB1 cannabinoid receptor, with a Ki of 0.8nM at CB1 and 9.5nM at CB2.
  • AM-919 — a potent agonist at both CB1 and CB2 with moderate selectivity for CB1, with a Ki of 2.2nM at CB1 and 3.4nM at CB2. It is a derivative of HU-210 and represents a hybrid structure between the classical and nonclassical cannabinoid families.
  • AM-926 — a potent agonist at both CB1 and CB2 with moderate selectivity for CB1, with a Ki of 2.2nM at CB1 and 4.3nM at CB2. It is a derivative of HU-210 and represents a hybrid structure between the classical and nonclassical cannabinoid families.
  • AM-938 — a potent agonist at both CB1 and CB2 with quadruple selectivity for CB2, with a Ki of 1.2nM at CB1 and 0.3nM at CB2. It is a derivative of HU-210 and represents a hybrid structure between the classical and nonclassical cannabinoid families.
  • AM-1116 — a dimethylated stereoisomer of anandamide whose Ki = 7.4nM at CB1.[3]
  • AM-1172 — an endocannabinoid analog specifically designed to be a potent and selective inhibitor of AEA uptake that is resistant to FAAH hydrolysis.
  • AM-1220 — a potent and selective analgesic CB1 agonist (as racemate) with a Ki of 3.88nM at CB1 and 73.4nM at CB2, giving it 19x selectivity for CB1. (R) enantiomer has around 1000x higher affinity for CB1 than (S) enantiomer.[8][9]
  • AM-1221 — a potent and selective CB2 agonist with a Ki of 0.28nM at CB2 and 52.3nM at CB1, giving it a selectivity of almost 187x.
  • AM-1235 — a moderately CB1 selective agonist, with a Ki of 1.5nM at CB1 and 20.4nM at CB2, giving it a selectivity of around 13x.[10]
  • AM-1241 — a potent and selective analgesic CB2 agonist with a Ki of 3.4nM at CB2 and 80x selectivity over CB1.[11]
  • AM-1248 — a moderately potent agonist with some selectivity for CB1, containing an unusual 3-(adamant-1-oyl) substitution on the indole ring.
  • AM-1710 — a CB2 selective cannabilactone with 54x selectivity over CB1.[12]
  • AM-1714 — a CB2 selective cannabilactone with 490x selectivity over CB1.[12]
  • AM-2201 — a potent agonist at both CB1 and CB2 with moderate selectivity for CB1, with a Ki of 1.0nM at CB1 and 2.6nM at CB2.
  • AM-2212 — a potent agonist at both CB1 and CB2 with dodecal selectivity for CB1, with a Ki of 1.4nM at CB1 and 18.9nM at CB2.[5]
  • AM-2213 — a potent agonist at both CB1 and CB2 with 10x selectivity for CB1, with a Ki of 3.0M at CB1 and 30nM at CB2.[5]
  • AM-2232 — a potent agonist at both CB1 and CB2, with a Ki of 0.28nM at CB1 and 1.48nM at CB2.[10]
  • AM-2233 — (R) enantiomer is potent and selective CB1 agonist used in 131I radiolabelled form to map distribution of CB1 receptors in brain.[13][14][15][16][17][18]
  • AM-2389 — classical cannabinoid derivative with 26x selectivity for CB1.
  • AM-3102 — an analog of oleoylethanolamide, the endogenous agonist for proliferator-activated receptor α (PPARα). It also acts as a weak cannabinoid agonist with Ki values of 33µM at CB1 and 26µM at CB2.
  • AM-4030 — a potent agonist at both CB1 and CB2, it is dodecally selective for CB1, with a Ki of 0.7nM at CB1 and 8.6nM at CB2. It is a derivative of HU-210 and represents a hybrid structure between the classical and nonclassical cannabinoid families.
  • AM-4054 — a potent but slow-onset agonist with CB1 affinity of 2.2nM and a 40x selectivity for CB1 over CB2.[19][20]
  • AM-4054 —
  • AM-4113 — a CB1 selective neutral antagonist.[21]
  • AM-6545 — a peripherally selective silent antagonist of CB1 receptors.

See also


References

  1. ↑ 1.0 1.1 Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ 3.0 3.1 3.2 3.3 Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ 5.0 5.1 5.2 Hongfeng Deng. Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs. PhD Dissertation, University of Connecticut, 2000.
  6. ↑ WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07 
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  9. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  10. ↑ 10.0 10.1 US patent 7241799, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2007-07-10 
  11. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  12. ↑ 12.0 12.1 Lua error in package.lua at line 80: module 'strict' not found.
  13. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  14. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  15. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  16. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  17. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  18. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  19. ↑ [Paronis CA, Thakur GA, Vemuri K, Makriyannis A, Bergman J. Effects of a Selective Cannabinoid Agonist and Antagonist on Body Temperature in Rats. The FASEB Journal. April 2007 21 (Meeting Abstract Supplement) A409. http://www.fasebj.org/cgi/content/meeting_abstract/21/5/A409]
  20. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  21. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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