AM-630

AM-630

Systematic (IUPAC) name
1-[2-(morpholin-4-yl)ethyl]-2-methyl-3-(4-methoxybenzoyl)-6-iodoindole
Clinical data
Pregnancy cat.	?
Legal status	?
Identifiers
CAS number	164178-33-0 N
ATC code	?
PubChem	CID 4302963
ChemSpider	3508738 Y
ChEMBL	CHEMBL181633 Y
Chemical data
Formula	C23H25IN2O3
Mol. mass	504.360 g/mol
SMILES	eMolecules & PubChem
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
N(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 32.1nM at CB₂ and 165x selectivity over CB₁, at which it acted as a weak partial agonist.^[1] 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.^[2][3] 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 a large number of related derivatives.^{[4][5][6][7][8]}

See also

• WIN 48,098 (Pravadoline)
• WIN 54,461 (6-Bromopravadoline)
• AM-1221

References

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): 665–72. doi:10.1038/sj.bjp.0702351. PMC 1565857. PMID 10188977. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=1565857. 
2. ^ 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. 
3. ^ Ishiguro H, Horiuchi Y, Ishikawa M, Koga M, Imai K, Suzuki Y, Morikawa M, Inada T, Watanabe Y, Takahashi M, Someya T, Ujike H, Iwata N, Ozaki N, Onaivi ES, Kunugi H, Sasaki T, Itokawa M, Arai M, Niizato K, Iritani S, Naka I, Ohashi J, Kakita A, Takahashi H, Nawa H, Arinami T (May 2010). "Brain cannabinoid CB2 receptor in schizophrenia". Biological Psychiatry 67 (10): 974–82. doi:10.1016/j.biopsych.2009.09.024. PMID 19931854. 
4. ^ Eissenstat, M. A.; Bell, M. R.; D'ambra, T. E.; Alexander, E. J.; Daum, S. J.; Ackerman, J. H.; Gruett, M. D.; Kumar, V. et al (1995). "Aminoalkylindoles: Structure-Activity Relationships of Novel Cannabinoid Mimetics". Journal of Medicinal Chemistry 38 (16): 3094. doi:10.1021/jm00016a013. PMID 7636873.  edit
5. ^ Hongfeng Deng. Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs. PhD Dissertation, University of Connecticut, 2000.
6. ^ Hynes J, Leftheris K, Wu H, Pandit C, Chen P, Norris DJ, Chen BC, Zhao R, Kiener PA, Chen X, Turk LA, Patil-Koota V, Gillooly KM, Shuster DJ, McIntyre KW (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. 
7. ^ Frost, J. M.; Dart, M. J.; Tietje, K. R.; Garrison, T. R.; Grayson, G. K.; Daza, A. V.; El-Kouhen, O. F.; Miller, L. N. 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. doi:10.1021/jm7011613. PMID 18311894.  edit
8. ^ Adam, J. M.; Cairns, J.; Caulfield, W.; Cowley, P.; Cumming, I.; Easson, M.; Edwards, D.; Ferguson, 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.  edit

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