AMG-3

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Chemical compound

title: "AMG-3" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["cannabinoids", "benzochromenes", "hydroxyarenes", "1,3-dithiolanes"] description: "Chemical compound" topic_path: "general/cannabinoids" source: "https://en.wikipedia.org/wiki/AMG-3" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477346872 | 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 | image = AMG-3 Structure.svg | image_class = skin-invert-image | width = 240

| tradename = | legal_status = | routes_of_administration =

| metabolism = | elimination_half-life = | excretion =

| CAS_number_Ref = | CAS_number = 179044-94-1 | UNII_Ref = | UNII = U90K6D923K | ChEMBL_Ref = | ChEMBL = 476325 | PubChem = 10002952 | ChemSpiderID_Ref = | ChemSpiderID = 8178532 | StdInChI_Ref = | StdInChI = 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 | StdInChIKey_Ref = | StdInChIKey = JECXXFXYJAQVAH-WOJBJXKFSA-N

| C=25 | H=36 | O=2 | S=2 | smiles = CCCCCCC4(SCCS4)c(cc1O)cc(OC(C)(C)C2CC=3)c1C2CC=3C

AMG-3 (part of the AM cannabinoid series) is an analgesic drug which is a cannabinoid agonist. It is a derivative of Δ8-THC substituted with a dithiolane group on the 3-position side chain. AMG-3 is a potent agonist at both CB1 and CB2 receptors with a Ki of 0.32 nM at CB1 and 0.52 nM at CB2, and its particularly high binding affinity has led to it being used as a template for further structural development of novel cannabinoid drugs. It has sedative and analgesic effects, with analgesia lasting for up to 36 hours after administration.

References

References

  1. (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.
  2. (March 1998). "Pharmacophoric requirements for cannabinoid side chains: multiple bond and C1'-substituted delta 8-tetrahydrocannabinols". Journal of Medicinal Chemistry.
  3. (July 2003). "Pharmacophoric requirements for the cannabinoid side chain. Probing the cannabinoid receptor subsite at C1'". Journal of Medicinal Chemistry.
  4. (December 2007). "Combined 3D QSAR and molecular docking studies to reveal novel cannabinoid ligands with optimum binding activity". Bioorganic & Medicinal Chemistry Letters.
  5. (September 2005). "Behavioral pharmacological properties of a novel cannabinoid 1',1'-dithiolane delta8-THC analog, AMG-3". Behavioural Pharmacology.

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cannabinoidsbenzochromeneshydroxyarenes1,3-dithiolanes