WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 524183
CAS#: 444912-75-8
Description: AM-2233 is a highly potent full agonist for the cannabinoid receptors. 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. 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.
MedKoo Cat#: 524183
Name: AM-2233
CAS#: 444912-75-8
Chemical Formula: C22H23IN2O
Exact Mass: 458.08551
Molecular Weight: 458.34
Elemental Analysis: C, 57.65; H, 5.06; I, 27.69; N, 6.11; O, 3.49
Synonym: AM-2233; AM 2233; AM2233; CHEMBL364266;
IUPAC/Chemical Name: 1-((N-Methylpiperidin-2-yl)methyl)-3-(2-iodobenzoyl)indole
InChi Key: KSLCYQTUSSEGPT-UHFFFAOYSA-N
InChi Code: 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
SMILES Code: CN1CCCCC1Cn2cc(C(=O)c3ccccc3I)c4ccccc24
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 458.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Berg T, Kaur L, Risnes A, Havig SM, Karinen R. Determination of a selection of synthetic cannabinoids and metabolites in urine by UHPSFC-MS/MS and by UHPLC-MS/MS. Drug Test Anal. 2015 Aug 25. doi: 10.1002/dta.1844. [Epub ahead of print] PubMed PMID: 26304456.
2: Uchiyama N, Kikura-Hanajiri R, Goda Y. Identification of a novel cannabimimetic phenylacetylindole, cannabipiperidiethanone, as a designer drug in a herbal product and its affinity for cannabinoid CB₁ and CB₂ receptors. Chem Pharm Bull (Tokyo). 2011;59(9):1203-5. PubMed PMID: 21881274.
3: Leung K. R-2-[(131)I]Iodophenyl-(1-(1-methylpiperidin-2-ylmethyl)-1H-indol-3-yl)methanone. 2006 Dec 12 [updated 2008 Feb 12]. Molecular Imaging and Contrast Agent Database (MICAD) [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2004-2013. Available from http://www.ncbi.nlm.nih.gov/books/NBK23641/ PubMed PMID: 20641836.
4: Fong TM, Guan XM, Marsh DJ, Shen CP, Stribling DS, Rosko KM, Lao J, Yu H, Feng Y, Xiao JC, Van der Ploeg LH, Goulet MT, Hagmann WK, Lin LS, Lanza TJ Jr, Jewell JP, Liu P, Shah SK, Qi H, Tong X, Wang J, Xu SS, Francis B, Strack AM, MacIntyre DE, Shearman LP. Antiobesity efficacy of a novel cannabinoid-1 receptor inverse agonist, N-[(1S,2S)-3-(4-chlorophenyl)-2-(3-cyanophenyl)-1-methylpropyl]-2-methyl-2-[[5-(t rifluoromethyl)pyridin-2-yl]oxy]propanamide (MK-0364), in rodents. J Pharmacol Exp Ther. 2007 Jun;321(3):1013-22. Epub 2007 Feb 27. PubMed PMID: 17327489.
5: Dhawan J, Deng H, Gatley SJ, Makriyannis A, Akinfeleye T, Bruneus M, Dimaio AA, Gifford AN. Evaluation of the in vivo receptor occupancy for the behavioral effects of cannabinoids using a radiolabeled cannabinoid receptor agonist, R-[125/131I]AM2233. Synapse. 2006 Aug;60(2):93-101. PubMed PMID: 16715483.
6: Shen CP, Xiao JC, Armstrong H, Hagmann W, Fong TM. F200A substitution in the third transmembrane helix of human cannabinoid CB1 receptor converts AM2233 from receptor agonist to inverse agonist. Eur J Pharmacol. 2006 Feb 15;531(1-3):41-6. Epub 2006 Jan 24. PubMed PMID: 16438957.
7: Deng H, Gifford AN, Zvonok AM, Cui G, Li X, Fan P, Deschamps JR, Flippen-Anderson JL, Gatley SJ, Makriyannis A. Potent cannabinergic indole analogues as radioiodinatable brain imaging agents for the CB1 cannabinoid receptor. J Med Chem. 2005 Oct 6;48(20):6386-92. PubMed PMID: 16190764.
