AM-630

AM-630
Legal status
Legal status	CA: Schedule II ; DE: NpSG (Industrial and scientific use only) ; UK: Under Psychoactive Substances Act ;
Identifiers
	IUPAC name 1-[2-(Morpholin-4-yl)ethyl]-2-methyl-3-(4-methoxybenzoyl)-6-iodoindole;
CAS Number	164178-33-0 ;
PubChem CID	4302963;
IUPHAR/BPS	750;
ChemSpider	3508738 ;
UNII	U1LNJ6NBKA;
ChEMBL	ChEMBL181633 ;
CompTox Dashboard (EPA)	DTXSID10167719 ;
ECHA InfoCard	100.229.964
Chemical and physical data
Formula	C23H25IN2O3
Molar mass	504.368 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C4COCCN4CCn(c1C)c2cc(I)ccc2c1C(=O)c3ccc(OC)cc3;
	InChI InChI=1S/C23H25IN2O3/c1-16-22(23(27)17-3-6-19(28-2)7-4-17)20-8-5-18(24)15-21(20)26(16)10-9-25-11-13-29-14-12-25/h3-8,15H,9-14H2,1-2H3 ; Key:JHOTYHDSLIUKCJ-UHFFFAOYSA-N ;
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AM-630 (6-Iodopravadoline) is a drug that acts as a potent and selective inverse agonist for the cannabinoid receptor CB₂, with a K_i of 32.1 nM at CB₂ and 165x selectivity over CB₁, at which it acted as a weak partial agonist.[1][2] It is used in the study of CB₂ mediated responses and has been used to investigate the possible role of CB₂ receptors in the brain.[3][4] AM-630 is significant as one of the first indole derived cannabinoid ligands substituted on the 6-position of the indole ring, a position that has subsequently been found to be important in determining affinity and efficacy at both the CB₁ and CB₂ receptors, and has led to the development of many related derivatives.[5][6][7][8][9]

References

Ruth A Ross; Heather C Brockie; Lesley A Stevenson; Vicki L Murphy; Fiona Templeton; Alexandros Makriyannis; Roger G Pertwee (February 1999). "Agonist-inverse agonist characterization at CB1 and CB2 cannabinoid receptors of L759633, L759656, and AM630". British Journal of Pharmacology. 126 (3): 665–72. doi:10.1038/sj.bjp.0702351. PMC 1565857. PMID 10188977.
Murataeva, N.; MacKie, K.; Straiker, A. (2012). "The CB2-preferring agonist JWH015 also potently and efficaciously activates CB1 in autaptic hippocampal neurons". Pharmacological Research. 66 (5): 437–42. doi:10.1016/j.phrs.2012.08.002. PMC 3601544. PMID 22921769.
Morgan NH, Stanford IM, Woodhall GL (September 2009). "Functional CB2 type cannabinoid receptors at CNS synapses". Neuropharmacology. 57 (4): 356–68. doi:10.1016/j.neuropharm.2009.07.017. PMID 19616018.
Ishiguro H; et al. (May 2010). "Brain cannabinoid CB2 receptor in schizophrenia". Biological Psychiatry. 67 (10): 974–82. doi:10.1016/j.biopsych.2009.09.024. PMID 19931854.
Eissenstat, M. A..; et al. (1995). "Aminoalkylindoles: Structure-Activity Relationships of Novel Cannabinoid Mimetics". Journal of Medicinal Chemistry. 38 (16): 3094–105. doi:10.1021/jm00016a013. PMID 7636873.
Hongfeng Deng. Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs. PhD Dissertation, University of Connecticut, 2000.
Hynes J; et al. (September 2002). "C-3 Amido-indole cannabinoid receptor modulators". Bioorganic & Medicinal Chemistry Letters. 12 (17): 2399–402. doi:10.1016/S0960-894X(02)00466-3. PMID 12161142.
Frost, J. M.; et al. (2008). "Indol-3-yl-tetramethylcyclopropyl Ketones: Effects of Indole Ring Substitution on CB2 Cannabinoid Receptor Activity". Journal of Medicinal Chemistry. 51 (6): 1904–12. doi:10.1021/jm7011613. PMID 18311894.
Adam, J. M.; et al. (2010). "Design, synthesis, and structure–activity relationships of indole-3-carboxamides as novel water soluble cannabinoid CB1 receptor agonists". MedChemComm. 1: 54. doi:10.1039/c0md00022a.

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[pmid10188977-1] Ruth A Ross; Heather C Brockie; Lesley A Stevenson; Vicki L Murphy; Fiona Templeton; Alexandros Makriyannis; Roger G Pertwee (February 1999). "Agonist-inverse agonist characterization at CB1 and CB2 cannabinoid receptors of L759633, L759656, and AM630". British Journal of Pharmacology. 126 (3): 665–72. doi:10.1038/sj.bjp.0702351. PMC 1565857. PMID 10188977.

[2] Murataeva, N.; MacKie, K.; Straiker, A. (2012). "The CB2-preferring agonist JWH015 also potently and efficaciously activates CB1 in autaptic hippocampal neurons". Pharmacological Research. 66 (5): 437–42. doi:10.1016/j.phrs.2012.08.002. PMC 3601544. PMID 22921769.

[pmid19616018-3] Morgan NH, Stanford IM, Woodhall GL (September 2009). "Functional CB2 type cannabinoid receptors at CNS synapses". Neuropharmacology. 57 (4): 356–68. doi:10.1016/j.neuropharm.2009.07.017. PMID 19616018.

[pmid19931854-4] Ishiguro H; et al. (May 2010). "Brain cannabinoid CB2 receptor in schizophrenia". Biological Psychiatry. 67 (10): 974–82. doi:10.1016/j.biopsych.2009.09.024. PMID 19931854.

[5] Eissenstat, M. A..; et al. (1995). "Aminoalkylindoles: Structure-Activity Relationships of Novel Cannabinoid Mimetics". Journal of Medicinal Chemistry. 38 (16): 3094–105. doi:10.1021/jm00016a013. PMID 7636873.

[6] Hongfeng Deng. Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs. PhD Dissertation, University of Connecticut, 2000.

[pmid12161142-7] Hynes J; et al. (September 2002). "C-3 Amido-indole cannabinoid receptor modulators". Bioorganic & Medicinal Chemistry Letters. 12 (17): 2399–402. doi:10.1016/S0960-894X(02)00466-3. PMID 12161142.

[8] Frost, J. M.; et al. (2008). "Indol-3-yl-tetramethylcyclopropyl Ketones: Effects of Indole Ring Substitution on CB2 Cannabinoid Receptor Activity". Journal of Medicinal Chemistry. 51 (6): 1904–12. doi:10.1021/jm7011613. PMID 18311894.

[9] Adam, J. M.; et al. (2010). "Design, synthesis, and structure–activity relationships of indole-3-carboxamides as novel water soluble cannabinoid CB1 receptor agonists". MedChemComm. 1: 54. doi:10.1039/c0md00022a.

AM-630

See also

References