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AMG-3

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Chemical compound

Pharmaceutical compound
AMG-3
Identifiers
IUPAC name
  • (6aR,10aR)-3-(2-hexyl-1,3-dithiolan-2-yl)-6,6,9-trimethyl-6a,7,10,10a-tetrahydrobenzochromen-1-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC25H36O2S2
Molar mass432.68 g·mol
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
  • Key:JECXXFXYJAQVAH-WOJBJXKFSA-N
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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 Δ-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.

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 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. S2CID 43377945.
  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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