AMG-3 explained

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.^[1] AMG-3 is a potent agonist at both CB₁ and CB₂ receptors with a K_i of 0.32 nM at CB₁ and 0.52 nM 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]

See also

• AMG-36
• AMG-41

Notes and References

1. Mavromoustakos T, Theodoropoulou E, Zervou M, Kourouli T, Papahatjis D . 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 . January 1999 . 9925329 . 10.1016/s0731-7085(98)00100-9 .
2. Papahatjis DP, Kourouli T, Abadji V, Goutopoulos A, Makriyannis A . Pharmacophoric requirements for cannabinoid side chains: multiple bond and C1'-substituted delta 8-tetrahydrocannabinols . Journal of Medicinal Chemistry . 41 . 7 . 1195–200 . March 1998 . 9544219 . 10.1021/jm970277i .
3. Papahatjis DP, Nikas SP, Kourouli T, Chari R, Xu W, Pertwee RG, Makriyannis A . Pharmacophoric requirements for the cannabinoid side chain. Probing the cannabinoid receptor subsite at C1' . Journal of Medicinal Chemistry . 46 . 15 . 3221–9 . July 2003 . 12852753 . 10.1021/jm020558c .
4. Durdagi S, Papadopoulos MG, Papahatjis DP, Mavromoustakos T . Combined 3D QSAR and molecular docking studies to reveal novel cannabinoid ligands with optimum binding activity . Bioorganic & Medicinal Chemistry Letters . 17 . 24 . 6754–63 . December 2007 . 17980589 . 10.1016/j.bmcl.2007.10.044 . 43377945 .
5. Antoniou K, Galanopoulos A, Vlachou S, Kourouli T, Nahmias V, Thermos K, Panagis G, Daifoti Z, Marselos M, Papahatjis D, Spyraki C . 6 . Behavioral pharmacological properties of a novel cannabinoid 1',1'-dithiolane delta8-THC analog, AMG-3 . Behavioural Pharmacology . 16 . 5–6 . 499–510 . September 2005 . 10.1097/00008877-200509000-00024 . 16148456 . 28054336 .