AM-7438

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]

AM-7438
Identifiers
IUPAC name
  • 3-cyanopropyl 2-[(6aR,10aR)-1-hydroxy-6,6,9-trimethyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-3-yl]-2-methylpropanoate
PubChem CID
ChEMBL
Chemical and physical data
FormulaC24H31NO4
Molar mass397.515 g·mol−1
3D model (JSmol)
SMILES
  • 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
  • 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


References
  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.
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