en AM-7438

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;
CAS Number	1577225-74-1 [EPA];
PubChem CID	89994983;
ChemSpider	76787992;
ChEMBL	ChEMBL4071389;
CompTox Dashboard (EPA)	DTXSID001336579 ;
Chemical and physical data
Formula	C24H31NO4
Molar mass	397.515 g·mol−1
3D model (JSmol)	Interactive image;
	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;

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]

References

^ 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.

[pmid25470070-1] 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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