AM-2233

AM-2233
Legal status
Legal status	CA: Schedule II; DE: Anlage II (Authorized trade only, not prescriptible); NZ: Temporary Class; UK: Class B;
Identifiers
	IUPAC name 1-[(N-methylpiperidin-2-yl)methyl]-3-(2-iodobenzoyl)indole;
CAS Number	444912-75-8 ;
PubChem CID	10226340;
ChemSpider	8401830 ;
UNII	Z489688DK3;
ChEMBL	ChEMBL364266 ;
CompTox Dashboard (EPA)	DTXSID401014171 ;
ECHA InfoCard	100.233.382
Chemical and physical data
Formula	C22H23IN2O
Molar mass	458.343 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Ic3ccccc3C(=O)c1cn(CC2CCCCN2C)c4c1cccc4;
	InChI 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 ; Key:KSLCYQTUSSEGPT-UHFFFAOYSA-N ;
	(what is this?) (verify)

AM-2233 is a drug that acts as a highly potent full agonist for the cannabinoid receptors, with a K_i 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]

It is notable for inducing tinnitus,^[9] though the reasons for this are unclear and may provide valuable insight into tinnitus research.

Legal Status

As of October 2015 AM-2233 is a controlled substance in China.^[10]

References

^ 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. 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 & Biology. 15 (11): 1207–1219. doi:10.1016/j.chembiol.2008.10.011. PMC 3700404. 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. 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.

[1] Hongfeng Deng (2000). Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs (PhD Dissertation). University of Connecticut. ProQuest 304624325.

[pmid16190764-2] 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.

[3] 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. ISBN 978-3-7643-7055-8.

[pmid16438957-4] 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.

[5] 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.

[pmid20641836-6] 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.

[7] 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. PMC 3700404. PMID 19022181.

[pmid21836461-8] 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. PMC 3212432. PMID 21836461.

[9] "AM-2233 INDUCED TINNITUS: COLLECTED REPORTS". 30 September 2014. Retrieved 5 April 2019.

[10] "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.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

[10]

Legal Status

See also

References