AM-2233 is a drug that acts as a highly potent full agonist for the cannabinoid receptors, with a Ki of 1.8 nM at CB1 and 2.2 nM at CB2 as the active (R) enantiomer.[1] It was developed as a selective radioligand for the cannabinoid receptors and has been used as its 131I derivative for mapping the distribution of the CB1 receptor in the brain.[2][3][4][5][6][7] AM-2233 was found to fully substitute for THC in rats, with a potency lower than that of JWH-018 but higher than WIN 55,212-2.[8]
^Hongfeng Deng (2000). Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs (PhD Dissertation). University of Connecticut. ProQuest 304624325.
^Deng H, Gifford AN, Zvonok AM, Cui G, Li X, Fan P, et al. (October 2005). "Potent cannabinergic indole analogues as radioiodinatable brain imaging agents for the CB1 cannabinoid receptor". Journal of Medicinal Chemistry. 48 (20): 6386–6392. doi:10.1021/jm050135l. PMID 16190764.
^Hanuš LR, Mechoulam R (2005). "Cannabinoid chemistry: an overview". Cannabinoids as Therapeutics. Milestones in Drug Therapy MDT. pp. 23–46. doi:10.1007/3-7643-7358-X_2. ISBN978-3-7643-7055-8.
^Shen CP, Xiao JC, Armstrong H, Hagmann W, Fong TM (February 2006). "F200A substitution in the third transmembrane helix of human cannabinoid CB1 receptor converts AM2233 from receptor agonist to inverse agonist". European Journal of Pharmacology. 531 (1–3): 41–46. doi:10.1016/j.ejphar.2005.12.026. PMID 16438957.
^Dhawan J, Deng H, Gatley SJ, Makriyannis A, Akinfeleye T, Bruneus M, et al. (August 2006). "Evaluation of the in vivo receptor occupancy for the behavioral effects of cannabinoids using a radiolabeled cannabinoid receptor agonist, R-[125/131I]AM2233". Synapse. 60 (2): 93–101. doi:10.1002/syn.20277. PMID 16715483. S2CID 21269336.
^Leung K (Dec 12, 2006). "R-2-[131I]Iodophenyl-(1-(1-methylpiperidin-2-ylmethyl)-1H-indol-3-yl)methanone". Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. PMID 20641836.
^Pei Y, Mercier RW, Anday JK, Thakur GA, Zvonok AM, Hurst D, et al. (November 2008). "Ligand-binding architecture of human CB2 cannabinoid receptor: evidence for receptor subtype-specific binding motif and modeling GPCR activation". Chemistry & Biology. 15 (11): 1207–1219. doi:10.1016/j.chembiol.2008.10.011. PMC3700404. PMID 19022181.
^Järbe TU, Deng H, Vadivel SK, Makriyannis A (September 2011). "Cannabinergic aminoalkylindoles, including AM678=JWH018 found in 'Spice', examined using drug (Δ(9)-tetrahydrocannabinol) discrimination for rats". Behavioural Pharmacology. 22 (5–6): 498–507. doi:10.1097/FBP.0b013e328349fbd5. PMC3212432. PMID 21836461.
^"AM-2233 INDUCED TINNITUS: COLLECTED REPORTS". 30 September 2014. Retrieved 5 April 2019.
^ (in Chinese). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.
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2233, drug, that, acts, highly, potent, full, agonist, cannabinoid, receptors, with, active, enantiomer, developed, selective, radioligand, cannabinoid, receptors, been, used, 131i, derivative, mapping, distribution, receptor, brain, found, fully, substitute, . AM 2233 is a drug that acts as a highly potent full agonist for the cannabinoid receptors with a Ki of 1 8 nM at CB1 and 2 2 nM at CB2 as the active R enantiomer 1 It was developed as a selective radioligand for the cannabinoid receptors and has been used as its 131I derivative for mapping the distribution of the CB1 receptor in the brain 2 3 4 5 6 7 AM 2233 was found to fully substitute for THC in rats with a potency lower than that of JWH 018 but higher than WIN 55 212 2 8 AM 2233Legal statusLegal statusCA Schedule II DE Anlage II Authorized trade only not prescriptible NZ Temporary Class UK Class BIdentifiersIUPAC name 1 N methylpiperidin 2 yl methyl 3 2 iodobenzoyl indoleCAS Number444912 75 8 NPubChem CID10226340ChemSpider8401830 YUNIIZ489688DK3ChEMBLChEMBL364266 YCompTox Dashboard EPA DTXSID401014171ECHA InfoCard100 233 382Chemical and physical dataFormulaC 22H 23I N 2OMolar mass458 343 g mol 13D model JSmol Interactive imageSMILES Ic3ccccc3C O c1cn CC2CCCCN2C c4c1cccc4InChI InChI 1S C22H23IN2O c1 24 13 7 6 8 16 24 14 25 15 19 17 9 3 5 12 21 17 25 22 26 18 10 2 4 11 20 18 23 h2 5 9 12 15 16H 6 8 13 14H2 1H3 YKey KSLCYQTUSSEGPT UHFFFAOYSA N Y N Y what is this verify It is notable for inducing tinnitus 9 though the reasons for this are unclear and may provide valuable insight into tinnitus research Legal Status EditAs of October 2015 AM 2233 is a controlled substance in China 10 See also EditAM 679 AM 694 AM 1220 AM 1221 AM 1235 AM 1241 AM 2232 Cannabipiperidiethanone FUBIMINA JWH 018 List of AM cannabinoids List of JWH cannabinoids List of HU cannabinoids List of designer drugsReferences Edit Hongfeng Deng 2000 Design and synthesis of selective cannabinoid receptor ligands Aminoalkylindole and other heterocyclic analogs PhD Dissertation University of Connecticut ProQuest 304624325 Deng H Gifford AN Zvonok AM Cui G Li X Fan P et al October 2005 Potent cannabinergic indole analogues as radioiodinatable brain imaging agents for the CB1 cannabinoid receptor Journal of Medicinal Chemistry 48 20 6386 6392 doi 10 1021 jm050135l PMID 16190764 Hanus LR Mechoulam R 2005 Cannabinoid chemistry an overview Cannabinoids as Therapeutics Milestones in Drug Therapy MDT pp 23 46 doi 10 1007 3 7643 7358 X 2 ISBN 978 3 7643 7055 8 Shen CP Xiao JC Armstrong H Hagmann W Fong TM February 2006 F200A substitution in the third transmembrane helix of human cannabinoid CB1 receptor converts AM2233 from receptor agonist to inverse agonist European Journal of Pharmacology 531 1 3 41 46 doi 10 1016 j ejphar 2005 12 026 PMID 16438957 Dhawan J Deng H Gatley SJ Makriyannis A Akinfeleye T Bruneus M et al August 2006 Evaluation of the in vivo receptor occupancy for the behavioral effects of cannabinoids using a radiolabeled cannabinoid receptor agonist R 125 131I AM2233 Synapse 60 2 93 101 doi 10 1002 syn 20277 PMID 16715483 S2CID 21269336 Leung K Dec 12 2006 R 2 131I Iodophenyl 1 1 methylpiperidin 2 ylmethyl 1H indol 3 yl methanone Molecular Imaging and Contrast Agent Database MICAD Internet PMID 20641836 Pei Y Mercier RW Anday JK Thakur GA Zvonok AM Hurst D et al November 2008 Ligand binding architecture of human CB2 cannabinoid receptor evidence for receptor subtype specific binding motif and modeling GPCR activation Chemistry amp Biology 15 11 1207 1219 doi 10 1016 j chembiol 2008 10 011 PMC 3700404 PMID 19022181 Jarbe TU Deng H Vadivel SK Makriyannis A September 2011 Cannabinergic aminoalkylindoles including AM678 JWH018 found in Spice examined using drug D 9 tetrahydrocannabinol discrimination for rats Behavioural Pharmacology 22 5 6 498 507 doi 10 1097 FBP 0b013e328349fbd5 PMC 3212432 PMID 21836461 AM 2233 INDUCED TINNITUS COLLECTED REPORTS 30 September 2014 Retrieved 5 April 2019 关于印发 非药用类麻醉药品和精神药品列管办法 的通知 in Chinese China Food and Drug Administration 27 September 2015 Archived from the original on 1 October 2015 Retrieved 1 October 2015 This cannabinoid related article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title AM 2233 amp oldid 1163066635, wikipedia, wiki, book, books, library,
