AMG-3

AMG-3

Systematic (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
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
ATC code	?
PubChem	CID 10002952
ChemSpider	8178532 N
ChEMBL	CHEMBL476325 N
Chemical data
Formula	C25H36O2S2
Mol. mass	432.681 g/mol
SMILES	eMolecules & PubChem
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
N(what is this?)  (verify)

AMG-3 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 K_i 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 24 hours after administration.^[5]

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-dibenzo[b,d]pyranyl)-2-hexyl-1,3-dithiolane and its methylated analog. Journal of Pharmaceutical and Biomedical Analysis. 1999 Jan;18(6):947-56. PMID 9925329
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. 1998 Mar 26;41(7):1195-200. PMID 9544219
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. 2003 Jul 17;46(15):3221-9. PMID 12852753
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 and Medicinal Chemistry Letters. 2007 Dec 15;17(24):6754-63. PMID 17980589
5. ^ Antoniou K, Galanopoulos A, Vlachou S, Kourouli T, Nahmias V, Thermos K, Panagis G, Daifoti Z, Marselos M, Papahatjis D, Spyraki C. Behavioral pharmacological properties of a novel cannabinoid 1',1'-dithiolane delta8-THC analog, AMG-3. Behavioural Pharmacology. 2005 Sep;16(5-6):499-510. PMID 16148456

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