AMG-3

AMG-3
Identifiers
	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;
CAS Number	179044-94-1 ;
PubChem CID	10002952;
ChemSpider	8178532 ;
UNII	U90K6D923K;
ChEMBL	ChEMBL476325 ;
CompTox Dashboard (EPA)	DTXSID701019037 ;
Chemical and physical data
Formula	C25H36O2S2
Molar mass	432.68 g·mol−1
3D model (JSmol)	Interactive image;
	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 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]

References

^ 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.
^ 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.
^ 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.
^ 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.
^ 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.

External links

Media related to AMG-3 at Wikimedia Commons

[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. 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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Identifiers

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
CAS Number	179044-94-1^N
PubChem CID	10002952
ChemSpider	8178532^N
UNII	U90K6D923K
ChEMBL	ChEMBL476325^N
CompTox Dashboard (EPA)	DTXSID701019037
Chemical and physical data
Formula	C₂₅H₃₆O₂S₂
Molar mass	432.68 g·mol⁻¹
3D model (JSmol)	Interactive image
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^N Key:JECXXFXYJAQVAH-WOJBJXKFSA-N^N
^NY (what is this?) (verify)

AMG-3

See also

References

External links