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 N
PubChem CID	4302963
IUPHAR/BPS	750
ChemSpider	3508738 Y
UNII	U1LNJ6NBKA
ChEMBL	ChEMBL181633 Y
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 Y Key:JHOTYHDSLIUKCJ-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

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]}

1. ^ Ross RA, Brockie HC, Stevenson LA, Murphy VL, Templeton F, Makriyannis A, Pertwee RG (February 1999). "Agonist-inverse agonist characterization at CB1 and CB2 cannabinoid receptors of L759633, L759656, and AM630". British Journal of Pharmacology. 126 (3): 665–672. doi:10.1038/sj.bjp.0702351. PMC 1565857. PMID 10188977.
2. ^ Murataeva N, Mackie K, Straiker A (November 2012). "The CB2-preferring agonist JWH015 also potently and efficaciously activates CB1 in autaptic hippocampal neurons". Pharmacological Research. 66 (5): 437–442. doi:10.1016/j.phrs.2012.08.002. PMC 3601544. PMID 22921769.
3. ^ Morgan NH, Stanford IM, Woodhall GL (September 2009). "Functional CB2 type cannabinoid receptors at CNS synapses". Neuropharmacology. 57 (4): 356–368. doi:10.1016/j.neuropharm.2009.07.017. PMID 19616018. S2CID 207224823.
4. ^ Ishiguro H, Horiuchi Y, Ishikawa M, Koga M, Imai K, Suzuki Y, et al. (May 2010). "Brain cannabinoid CB2 receptor in schizophrenia". Biological Psychiatry. 67 (10): 974–982. doi:10.1016/j.biopsych.2009.09.024. PMID 19931854. S2CID 14222913.
5. ^ Eissenstat MA, Bell MR, D'Ambra TE, Alexander EJ, Daum SJ, Ackerman JH, et al. (August 1995). "Aminoalkylindoles: structure-activity relationships of novel cannabinoid mimetics". Journal of Medicinal Chemistry. 38 (16): 3094–3105. 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.
7. ^ Hynes J, Leftheris K, Wu H, Pandit C, Chen P, Norris DJ, et al. (September 2002). "C-3 Amido-indole cannabinoid receptor modulators". Bioorganic & Medicinal Chemistry Letters. 12 (17): 2399–2402. doi:10.1016/S0960-894X(02)00466-3. PMID 12161142.
8. ^ Frost JM, Dart MJ, Tietje KR, Garrison TR, Grayson GK, Daza AV, et al. (March 2008). "Indol-3-yl-tetramethylcyclopropyl ketones: effects of indole ring substitution on CB2 cannabinoid receptor activity". Journal of Medicinal Chemistry. 51 (6): 1904–1912. 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.

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