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Chemical compound
AM-7438
3-cyanopropyl 2-[(6aR,10aR)-1-hydroxy-6,6,9-trimethyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-3-yl]-2-methylpropanoate
CAS Number PubChem CID ChemSpider ChEMBL CompTox Dashboard (EPA ) Formula C 24 H 31 N O 4 Molar mass 397.515 g·mol−1 3D model (JSmol )
CC1=CC[C@@H]2[C@@H](C1)C3=C(C=C(C=C3OC2(C)C)C(C)(C)C(=O)OCCCC#N)O
InChI=1S/C24H31NO4/c1-15-8-9-18-17(12-15)21-19(26)13-16(14-20(21)29-24(18,4)5)23(2,3)22(27)28-11-7-6-10-25/h8,13-14,17-18,26H,6-7,9,11-12H2,1-5H3/t17-,18-/m1/s1
Key:PGSJGFYQNYPKOJ-QZTJIDSGSA-N
AM-7438 is a drug which is a cannabinoid receptor agonist , developed by the research team led by Dr Alexandros Makriyannis . It is a derivative of Δ8-THC which has been substituted with a side chain containing a metabolically labile ester group, allowing the molecule to be rapidly metabolised to an inactive form, in a similar manner to drugs such as remifentanil , remimazolam and SN 35210 . This means that while AM-7438 retains potent cannabinoid effects, it has a much shorter duration of action than most related compounds.[ 1]
^ Nikas SP, Sharma R, Paronis CA, Kulkarni S, Thakur GA, Hurst D, Wood JT, Gifford RS, Rajarshi G, Liu Y, Raghav JG, Guo JJ, Järbe TU, Reggio PH, Bergman J, Makriyannis A (January 2015). "Probing the carboxyester side chain in controlled deactivation (−)-δ(8)-tetrahydrocannabinols" . Journal of Medicinal Chemistry . 58 (2): 665–81. doi :10.1021/jm501165d . PMC 4306527 . PMID 25470070 .
Phytocannabinoids (comparison )
Cannabibutols Cannabichromenes Cannabicyclols Cannabidiols Cannabielsoins Cannabigerols Cannabiphorols Cannabinols Cannabitriols Cannabivarins Delta-8-tetrahydrocannabinols Delta-9-tetrahydrocannabinols Delta-10-Tetrahydrocannabinols Miscellaneous cannabinoids Active metabolites
Endocannabinoids Synthetic cannabinoid receptor agonists / neocannabinoids
Classical cannabinoids (dibenzopyrans) Non-classical cannabinoids Adamantoylindoles Benzimidazoles Benzoylindoles Cyclohexylphenols Eicosanoids Indazole-3- carboxamides Indole-3-carboxamides Indole-3-carboxylates Naphthoylindazoles Naphthoylindoles Naphthoylpyrroles Naphthylmethylindenes Naphthylmethylindoles Phenylacetylindoles Pyrazolecarboxamides Tetramethylcyclo- propanoylindazoles Tetramethylcyclo- propanoylindoles Others
Allosteric CBR Tooltip Cannabinoid receptor ligands Endocannabinoid enhancers (inactivation inhibitors) Anticannabinoids (antagonists/inverse agonists/antibodies)