AMG-3

AMG-3 (part of the AM cannabinoid series) is an analgesic drug which is a cannabinoid agonist. It is a derivative of Δ8THC substituted with a dithiolane group on the 3-position side chain.[1] AMG-3 is a potent agonist at both CB1 and CB2 receptors with a Ki of 0.32nM at CB1 and 0.52nM at CB2,[2][3] and its particularly high binding affinity has led to it being used as a template for further structural development of novel cannabinoid drugs.[4] It has sedative and analgesic effects, with analgesia lasting for up to 36 hours after administration.[5]

AMG-3
Identifiers
IUPAC name
  • (6aR,10aR)-3-(2-hexyl-1,3-dithiolan-2-yl)-6,6,9-trimethyl-6a,7,10,10a-tetrahydrobenzo[c]chromen-1-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC25H36O2S2
Molar mass432.68 g·mol−1
3D model (JSmol)
SMILES
  • CCCCCCC4(SCCS4)c(cc1O)cc(OC(C)(C)C2CC=3)c1C2CC=3C
InChI
  • InChI=1S/C25H36O2S2/c1-5-6-7-8-11-25(28-12-13-29-25)18-15-21(26)23-19-14-17(2)9-10-20(19)24(3,4)27-22(23)16-18/h9,15-16,19-20,26H,5-8,10-14H2,1-4H3/t19-,20-/m1/s1 N
  • Key:JECXXFXYJAQVAH-WOJBJXKFSA-N N
 NY (what is this?)  (verify)

See also

References
  1. Mavromoustakos T, Theodoropoulou E, Zervou M, Kourouli T, Papahatjis D (January 1999). "Structure elucidation and conformational properties of synthetic cannabinoids (-)-2-(6a,7,10,10a-tetrahydro-6,6,9-trimethyl-1-hydroxy-6H-dibe nzo [b,d]pyranyl)-2-hexyl-1,3-dithiolane and its methylated analog". Journal of Pharmaceutical and Biomedical Analysis. 18 (6): 947–56. doi:10.1016/s0731-7085(98)00100-9. PMID 9925329.
  2. Papahatjis DP, Kourouli T, Abadji V, Goutopoulos A, Makriyannis A (March 1998). "Pharmacophoric requirements for cannabinoid side chains: multiple bond and C1'-substituted delta 8-tetrahydrocannabinols". Journal of Medicinal Chemistry. 41 (7): 1195–200. doi:10.1021/jm970277i. PMID 9544219.
  3. Papahatjis DP, Nikas SP, Kourouli T, Chari R, Xu W, Pertwee RG, Makriyannis A (July 2003). "Pharmacophoric requirements for the cannabinoid side chain. Probing the cannabinoid receptor subsite at C1'". Journal of Medicinal Chemistry. 46 (15): 3221–9. doi:10.1021/jm020558c. PMID 12852753.
  4. Durdagi S, Papadopoulos MG, Papahatjis DP, Mavromoustakos T (December 2007). "Combined 3D QSAR and molecular docking studies to reveal novel cannabinoid ligands with optimum binding activity". Bioorganic & Medicinal Chemistry Letters. 17 (24): 6754–63. doi:10.1016/j.bmcl.2007.10.044. PMID 17980589.
  5. Antoniou K, Galanopoulos A, Vlachou S, Kourouli T, Nahmias V, Thermos K, et al. (September 2005). "Behavioral pharmacological properties of a novel cannabinoid 1',1'-dithiolane delta8-THC analog, AMG-3". Behavioural Pharmacology. 16 (5–6): 499–510. doi:10.1097/00008877-200509000-00024. PMID 16148456. S2CID 28054336.
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