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Molar mass432.68 g·mol−1
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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]

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  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. PMID 16148456.