AM-630

AM-630
IUPAC ime
	1-[2-(morfolin-4-il)etil]-2-metil-3-(4-metoksibenzoil)-6-jodoindol
Identifikatori
CAS broj	164178-33-0
ATC kod	none
PubChem	CID 4302963
ChemSpider	3508738
ChEMBL	CHEMBL181633
Hemijski podaci
Formula	C23H25IN2O3
Molarna masa	504,360 g/mol
	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 ;

AM-630 (6-Jodopravadolin) je lek koji deluje kao potentan i selektivan inverzni agonist za kanabinoidni receptor CB₂, sa K_i od 32,1 nM na CB₂ i 165x selektivnošću u odnosu na CB₁, na kome deluje kao slab parcijalni agonist.^[1] On se koristi u istraživanju CB₂ posredovanih responsa i korišten je za istraživanje moguće uloge CB₂ receptora u mozgu.^[2]^[3] AM-630 je značajan kao jedan od prvih indolnih kanabinoidnih liganda supstituisanih na 6-poziciji indolnog prstena, za koju je naknadno utvrđena da je važna u određivanju afiniteta i efikasnosti na CB₁ i CB₂ receptorima. To je dovelo do razvoja znatnog broja srodnih jedinjenja.^[4]^[5]^[6]^[7]^[8]

Reference

^ Ross RA, Brockie HC, Stevenson LA, Murphy VL, Templeton F, Makriyannis A, Pertwee RG (1999). „Agonist-inverse agonist characterization at CB1 and CB2 cannabinoid receptors of L759633, L759656, and AM630”. British Journal of Pharmacology. 126 (3): 665—72. PMC 1565857  . PMID 10188977. doi:10.1038/sj.bjp.0702351.
^ Morgan NH, Stanford IM, Woodhall GL (2009). „Functional CB2 type cannabinoid receptors at CNS synapses”. Neuropharmacology. 57 (4): 356—68. PMID 19616018. doi:10.1016/j.neuropharm.2009.07.017.
^ 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 (2010). „Brain cannabinoid CB2 receptor in schizophrenia”. Biological Psychiatry. 67 (10): 974—82. PMID 19931854. doi:10.1016/j.biopsych.2009.09.024.
^ Eissenstat, M. A.; Bell, M. R.; D'ambra, T. E.; Alexander, E. J.; Daum, S. J.; Ackerman, J. H.; Gruett, M. D.; Kumar, V.; Estep, K. G. (1995). „Aminoalkylindoles: Structure-Activity Relationships of Novel Cannabinoid Mimetics”. Journal of Medicinal Chemistry. 38 (16): 3094. PMID 7636873. doi:10.1021/jm00016a013.
^ Hongfeng Deng. Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs. PhD Dissertation, University of Connecticut, 2000.
^ 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 (2002). „C-3 Amido-indole cannabinoid receptor modulators”. Bioorganic & Medicinal Chemistry Letters. 12 (17): 2399—402. PMID 12161142. doi:10.1016/S0960-894X(02)00466-3.
^ 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.; Li, L. (2008). „Indol-3-yl-tetramethylcyclopropyl Ketones: Effects of Indole Ring Substitution on CB2 Cannabinoid Receptor Activity”. Journal of Medicinal Chemistry. 51 (6): 1904. PMID 18311894. doi:10.1021/jm7011613.
^ Adam, J. M.; Cairns, J.; Caulfield, W.; Cowley, P.; Cumming, I.; Easson, M.; Edwards, D.; Ferguson, M.; Goodwin, R. (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.

Vidi još

WIN 48,098 (Pravadolin)
WIN 54,461 (6-Bromopravadolin)
AM-1221

[pmid10188977-1] Ross RA, Brockie HC, Stevenson LA, Murphy VL, Templeton F, Makriyannis A, Pertwee RG (1999). „Agonist-inverse agonist characterization at CB1 and CB2 cannabinoid receptors of L759633, L759656, and AM630”. British Journal of Pharmacology. 126 (3): 665—72. PMC 1565857  . PMID 10188977. doi:10.1038/sj.bjp.0702351.

[pmid19616018-2] Morgan NH, Stanford IM, Woodhall GL (2009). „Functional CB2 type cannabinoid receptors at CNS synapses”. Neuropharmacology. 57 (4): 356—68. PMID 19616018. doi:10.1016/j.neuropharm.2009.07.017.

[pmid19931854-3] 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 (2010). „Brain cannabinoid CB2 receptor in schizophrenia”. Biological Psychiatry. 67 (10): 974—82. PMID 19931854. doi:10.1016/j.biopsych.2009.09.024.

[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.; Estep, K. G. (1995). „Aminoalkylindoles: Structure-Activity Relationships of Novel Cannabinoid Mimetics”. Journal of Medicinal Chemistry. 38 (16): 3094. PMID 7636873. doi:10.1021/jm00016a013.

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

[pmid12161142-6] 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 (2002). „C-3 Amido-indole cannabinoid receptor modulators”. Bioorganic & Medicinal Chemistry Letters. 12 (17): 2399—402. PMID 12161142. doi:10.1016/S0960-894X(02)00466-3.

[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.; Li, L. (2008). „Indol-3-yl-tetramethylcyclopropyl Ketones: Effects of Indole Ring Substitution on CB2 Cannabinoid Receptor Activity”. Journal of Medicinal Chemistry. 51 (6): 1904. PMID 18311894. doi:10.1021/jm7011613.

[8] Adam, J. M.; Cairns, J.; Caulfield, W.; Cowley, P.; Cumming, I.; Easson, M.; Edwards, D.; Ferguson, M.; Goodwin, R. (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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