AM-2233

Summary

AM-2233 is a pharmaceutical compound recognized for its exceptional role as a potent full agonist for cannabinoid receptors. Specifically, the (R) enantiomer of AM-2233 exhibits a remarkable Ki of 1.8 nM at CB1 and 2.2 nM at CB2, underscoring its potent activity at these receptors.
One of its primary purposes is as a selective radioligand designed for studying cannabinoid receptors. Notably, AM-2233, in its 131I derivative form, has been instrumental in mapping the distribution of CB1 receptors within the brain, contributing to our understanding of cannabinoid receptor localization.
In research involving rats, AM-2233 has demonstrated the ability to fully substitute for THC, although its potency falls between that of JWH-018 and WIN 55,212-2, offering insights into the comparative effects of these compounds.
Moreover, AM-2233 is notable for its capacity to induce tinnitus, a phenomenon that has yet to be fully elucidate. This unique trait may hold valuable insights for ongoing research into tinnitus and its underlying mechanisms.

Identifiers

IUPAC name
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

Legal Status

As of October 2015 AM-2233 is a controlled substance in China.

FAQ

• What is AM-2233, and what are its primary pharmacological characteristics?
• AM-2233 is a pharmaceutical compound known for its role as a highly potent full agonist for cannabinoid receptors. Specifically, the (R) enantiomer of AM-2233 exhibits a remarkable Ki of 1.8 nM at CB1 and 2.2 nM at CB2, indicating its potent activity at these receptors.
• Why was AM-2233 developed, and how is it used in cannabinoid research?
• AM-2233 was initially developed as a selective radioligand for cannabinoid receptors. Its 131I derivative has been instrumental in mapping the distribution of CB1 receptors in the brain, aiding researchers in understanding the localization of these receptors.
• In what way does AM-2233 compare to other cannabinoids like THC, JWH-018, and WIN 55,212-2?
• In rat studies, AM-2233 has been found to substitute for THC fully. Its potency falls between that of JWH-018 and WIN 55,212-2, providing insights into the relative effects and interactions of these compounds.
• What is the significance of AM-2233 inducing tinnitus, and how can it contribute to tinnitus research?
• AM-2233 is known for its ability to induce tinnitus, a phenomenon not yet fully understood. Research into this unique property may offer valuable insights into the underlying mechanisms of tinnitus and aid in tinnitus research.
• Is AM 2233 available for medical or recreational use?
• AM-2233 is primarily used for research, particularly in cannabinoid receptor studies. It is essential to adhere to local and national regulations when working with compounds not approved for medical or recreational use in humans.
• Where can I find more information about AM-2233 and its applications in cannabinoid research?
• To delve deeper into AM-2233 and its role in cannabinoid research, you can explore scientific journals and academic databases and seek guidance from experts in cannabinoid pharmacology. Always ensure compliance with safety and legal guidelines when researching or handling such substances.

References

1. Hongfeng Deng’s 2000 PhD Dissertation from the University of Connecticut focuses on the design and synthesis of selective cannabinoid receptor ligands, including aminoalkylindole and other heterocyclic analogs. This work delves into the development of compounds targeting cannabinoid receptors for various research and potential applications.
2. Deng H, Gifford AN, Zvonok AM, and colleagues (October 2005) explored potent cannabinergic indole analogues as radioiodinatable brain imaging agents for the CB1 cannabinoid receptor. Published in the “Journal of Medicinal Chemistry” (48(20), 6386–6392), their research contributed to the development of imaging agents for studying cannabinoid receptors in the brain.
3. Hanuš LR and Mechoulam R provided an overview of cannabinoid chemistry in 2005, emphasizing its role in therapeutic applications. This information can be found in the book “Cannabinoids as Therapeutics” (Milestones in Drug Therapy MDT), offering insights into the chemical aspects of cannabinoids.
4. In February 2006, Shen CP, Xiao JC, Armstrong H, Hagmann W, and Fong TM investigated the effects of the F200A substitution in the third transmembrane helix of the human cannabinoid CB1 receptor on compounds like AM2233. Their findings, published in the “European Journal of Pharmacology” (531(1–3), 41–46), shed light on the structural factors affecting receptor interactions.
5. Dhawan J, Deng H, Gatley SJ, and colleagues (August 2006) evaluated in vivo receptor occupancy for the behavioral effects of cannabinoids using a radiolabeled cannabinoid receptor agonist, R-[125/131I]AM2233. Published in “Synapse” (60(2), 93–101), this research provided insights into the relationship between receptor occupancy and the behavioral effects of cannabinoids.
6. Leung K’s work on “R-2-[131I]Iodophenyl-(1-(1-methylpiperidin-2-ylmethyl)-1H-indol-3-yl)methanone” offers insights into radiolabeled compounds used for imaging studies. This information can be accessed in the Molecular Imaging and Contrast Agent Database (MICAD).
7. Pei Y, Mercier RW, Anday JK, and colleagues (November 2008) delved into the ligand-binding architecture of the human CB2 cannabinoid receptor. Their research, published in “Chemistry & Biology” (15(11), 1207–1219), provided evidence for receptor subtype-specific binding motifs and offered models for GPCR activation specific to CB2 receptors.
8. Järbe TU, Deng H, Vadivel SK, and Makriyannis A (September 2011) examined cannabinergic aminoalkylindoles, including AM678=JWH018, found in ‘Spice’, using drug discrimination for rats. Their research, featured in “Behavioural Pharmacology” (22(5–6), 498–507), explored the discriminative effects of these compounds in rats, shedding light on their behavioral impact.
9. The collection of reports on “AM-2233 INDUCED TINNITUS” offers insights into the phenomenon of tinnitus induced by AM-2233. Tinnitus, a perception of noise in the ears without external sound, has been associated with this compound, although the reasons remain unclear.
10. A notice from the China Food and Drug Administration (CFDA) in Chinese, dated September 27, 2015, pertains to the regulation of non-medical narcotics and psychotropic substances. The document highlights regulatory measures related to these substances in China.