AM-2233: Difference between revisions

| verifiedrevid = 451603691

| IUPAC_name = 1-[(N-methylpiperidin-2-yl)methyl]-3-(2-iodobenzoyl)indole

| legal_CA = <!-- / Schedule I, II, III, IV, V, VI, VII, VIII -->

| legal_UK = <!-- GSL / P / POM / CD / Class A, B, C -->

| legal_status =

| routes_of_administration =

| excretion =

| CAS_number = <!-- blanked - oldvalue: 444912-75-8 -->

| molecular_weight = 458.334 g/mol

'''AM-2233''' is a drug which acts as a highly potent [[full agonist]] for the [[cannabinoid receptor]]s, with a [[Dissociation constant|K_i]] of 1.8nM at [[Cannabinoid receptor 1|CB₁]] and 2.2nM at [[Cannabinoid receptor 2|CB₂]] as the active (R) [[enantiomer]].<ref>[http://proquest.umi.com/pqdlink?did=726066941&Fmt=7&clientId=79356&RQT=309&VName=PQD Hongfeng Deng. Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs. PhD Dissertation, University of Connecticut, 2000.]</ref> It was developed as a selective [[isotopic labelling|radioligand]] for the cannabinoid receptors and has been used as its [[Iodine-131|¹³¹I]] derivative for mapping the distribution of the CB₁ receptor in the brain.<ref name="pmid16190764">{{cite journal |author=Deng H, Gifford AN, Zvonok AM, Cui G, Li X, Fan P, Deschamps JR, Flippen-Anderson JL, Gatley SJ, Makriyannis A |title=Potent cannabinergic indole analogues as radioiodinatable brain imaging agents for the CB1 cannabinoid receptor |journal=Journal of Medicinal Chemistry |volume=48 |issue=20 |pages=6386–92 |year=2005 |month=October |pmid=16190764 |doi=10.1021/jm050135l |url=}}</ref><ref>{{cite doi|10.1007/3-7643-7358-X_2}}</ref><ref name="pmid16438957">{{cite journal |author=Shen CP, Xiao JC, Armstrong H, Hagmann W, Fong TM |title=F200A substitution in the third transmembrane helix of human cannabinoid CB1 receptor converts AM2233 from receptor agonist to inverse agonist |journal=European Journal of Pharmacology |volume=531 |issue=1–3 |pages=41–6 |year=2006 |month=February |pmid=16438957 |doi=10.1016/j.ejphar.2005.12.026 |url=}}</ref><ref>{{cite doi|10.1002/syn.20277}}</ref><ref name="pmid20641836">{{cite journal |author=Leung K |title=R-2-[131I]Iodophenyl-(1-(1-methylpiperidin-2-ylmethyl)-1H-indol-3-yl)methanone |journal=Molecular Imaging and Contrast Agent Database (MICAD) [Internet] |volume= |issue= |pages= |year=2006 Dec 12 |pmid=20641836 |doi= |url=}}</ref><ref>{{cite doi|10.1016/j.chembiol.2008.10.011}}</ref> AM-2233 was found to fully substitute for [[tetrahydrocannabinol|THC]] in rats, with a potency lower than that of [[JWH-018]] but higher than [[WIN 55,212-2]].<ref name="pmid21836461">{{cite journal |author=Järbe TU, Deng H, Vadivel SK, Makriyannis A |title=Cannabinergic aminoalkylindoles, including AM678=JWH018 found in 'Spice', examined using drug (Δ9-tetrahydrocannabinol) discrimination for rats |journal=Behavioural Pharmacology |volume=22 |issue=5-6 |pages=498–507 |year=2011 |month=September |pmid=21836461 |doi=10.1097/FBP.0b013e328349fbd5 |url=}}</ref>

==See also==

==References==

<references/>

[[Category:Cannabinoids]]

[[Category:Organoiodides]]