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MedKoo Cat#: 531444 | Name: AM281
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

AM281 is a synthetic cannabinoid CB1 receptor antagonist. In a study of rats in morphine withdrawal, administration of AM281 at the doses: 0.1, 0.5 and 1.0mg/kg significantly improved acquisition of information, while 0.1 and 0.5mg/kg of AM281 significantly facilitated consolidation process. Not only did AM281 not affect locomotor and exploratory activity, but also anxiety. This is the first evidence that AM281 exerts facilitatory effect on recognition memory in rats. This effect seems to be memory specific because no alterations in animals' psychomotor activity and anxiety were observed.

Chemical Structure

AM281
AM281
CAS#202463-68-1

Theoretical Analysis

MedKoo Cat#: 531444

Name: AM281

CAS#: 202463-68-1

Chemical Formula: C21H19Cl2IN4O2

Exact Mass: 555.9930

Molecular Weight: 557.21

Elemental Analysis: C, 45.27; H, 3.44; Cl, 12.72; I, 22.77; N, 10.06; O, 5.74

Price and Availability

Size Price Availability Quantity
5mg USD 285.00 2 Weeks
10mg USD 485.00 2 Weeks
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Related CAS #
No Data
Synonym
AM281; AM 281; AM-281
IUPAC/Chemical Name
1-(2,4-dichlorophenyl)-5-(4-iodophenyl)-4-methyl-N-morpholin-4-ylpyrazole-3-carboxamide
InChi Key
AJFFBPZYXRNAIC-UHFFFAOYSA-N
InChi Code
InChI=1S/C21H19Cl2IN4O2/c1-13-19(21(29)26-27-8-10-30-11-9-27)25-28(18-7-4-15(22)12-17(18)23)20(13)14-2-5-16(24)6-3-14/h2-7,12H,8-11H2,1H3,(H,26,29)
SMILES Code
O=C(C1=NN(C2=CC=C(Cl)C=C2Cl)C(C3=CC=C(I)C=C3)=C1C)NN4CCOCC4
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
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
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
AM281 is a selective CB1 receptor antagonist with an IC50 of 9.91 nM. AM281 inhibits CB2 receptor with an IC50 of 13000 nM.42.
In vitro activity:
TBD
In vivo activity:
Fig. 3A shows the time spent in the non-preferred area during the pre- and post-conditioning phases of the CPP. The CPP scores of rats treated with AM281 for 7 or 14 days prior to the start of the CPP are presented in Fig. 3B. Two-way ANOVA showed a significant effect in treatments [F (1, 24)=16.25, P<0.001], but not in pretreatment days or treatments×pretreatment days interaction. Bonferroni's posttest revealed that rats pretreated with AM281 for 14 days showed significant CPP towards the drug (P<0.01). Reference: Eur J Pharmacol. 2015 Nov 5;766:135-41. https://pubmed.ncbi.nlm.nih.gov/26450088/
Solvent mg/mL mM comments
Solubility
DMSO 21.4 38.41
DMF 1.0 1.79
DMF:PBS (pH 7.2) (1:5) 0.2 0.36
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 557.21 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.

Recalculate based on batch purity %
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
Formulation protocol:
1. Bialuk I, Winnicka MM. Facilitatory effect of AM281 on recognition memory in rats. Pharmacol Rep. 2016 Apr;68(2):301-9. doi: 10.1016/j.pharep.2015.09.008. Epub 2015 Oct 9. PMID: 26922532. 2. Botanas CJ, de la Peña JB, Dela Pena IJ, Tampus R, Kim HJ, Yoon SS, Seo JW, Jeong EJ, Cheong JH. Evaluation of the abuse potential of AM281, a new synthetic cannabinoid CB1 receptor antagonist. Eur J Pharmacol. 2015 Nov 5;766:135-41. doi: 10.1016/j.ejphar.2015.10.004. Epub 2015 Oct 9. PMID: 26450088.
In vitro protocol:
TBD
In vivo protocol:
1. Bialuk I, Winnicka MM. Facilitatory effect of AM281 on recognition memory in rats. Pharmacol Rep. 2016 Apr;68(2):301-9. doi: 10.1016/j.pharep.2015.09.008. Epub 2015 Oct 9. PMID: 26922532. 2. Botanas CJ, de la Peña JB, Dela Pena IJ, Tampus R, Kim HJ, Yoon SS, Seo JW, Jeong EJ, Cheong JH. Evaluation of the abuse potential of AM281, a new synthetic cannabinoid CB1 receptor antagonist. Eur J Pharmacol. 2015 Nov 5;766:135-41. doi: 10.1016/j.ejphar.2015.10.004. Epub 2015 Oct 9. PMID: 26450088.
1: Sidibeh CO, Pereira MJ, Lau Börjesson J, Kamble PG, Skrtic S, Katsogiannos P, Sundbom M, Svensson MK, Eriksson JW. Role of cannabinoid receptor 1 in human adipose tissue for lipolysis regulation and insulin resistance. Endocrine. 2016 Nov 17. [Epub ahead of print] PubMed PMID: 27858284. 2: Martins DF, Siteneski A, Ludtke DD, Dal-Secco D, Santos AR. High-Intensity Swimming Exercise Decreases Glutamate-Induced Nociception by Activation of G-Protein-Coupled Receptors Inhibiting Phosphorylated Protein Kinase A. Mol Neurobiol. 2016 Sep 13. [Epub ahead of print] PubMed PMID: 27624384. 3: Pava MJ, Makriyannis A, Lovinger DM. Endocannabinoid Signaling Regulates Sleep Stability. PLoS One. 2016 Mar 31;11(3):e0152473. doi: 10.1371/journal.pone.0152473. PubMed PMID: 27031992; PubMed Central PMCID: PMC4816426. 4: Wang L, Yang L, Tian L, Mai P, Jia S, Yang L, Li L. Cannabinoid Receptor 1 Mediates Homing of Bone Marrow-Derived Mesenchymal Stem Cells Triggered by Chronic Liver Injury. J Cell Physiol. 2017 Jan;232(1):110-21. doi: 10.1002/jcp.25395. PubMed PMID: 27028843. 5: Bialuk I, Winnicka MM. Facilitatory effect of AM281 on recognition memory in rats. Pharmacol Rep. 2016 Apr;68(2):301-9. doi: 10.1016/j.pharep.2015.09.008. PubMed PMID: 26922532. 6: Botanas CJ, de la Peña JB, Dela Pena IJ, Tampus R, Kim HJ, Yoon SS, Seo JW, Jeong EJ, Cheong JH. Evaluation of the abuse potential of AM281, a new synthetic cannabinoid CB1 receptor antagonist. Eur J Pharmacol. 2015 Nov 5;766:135-41. doi: 10.1016/j.ejphar.2015.10.004. PubMed PMID: 26450088. 7: Toguri JT, Moxsom R, Szczesniak AM, Zhou J, Kelly ME, Lehmann C. Cannabinoid 2 receptor activation reduces leukocyte adhesion and improves capillary perfusion in the iridial microvasculature during systemic inflammation. Clin Hemorheol Microcirc. 2015;61(2):237-49. doi: 10.3233/CH-151996. PubMed PMID: 26410875. 8: Juszczak K, Maciukiewicz P. The role of the peripheral cannabinoid system in the pathogenesis of detrusor overactivity evoked by increased intravesical osmolarity in rats. Can J Physiol Pharmacol. 2015 Aug;93(8):721-6. doi: 10.1139/cjpp-2015-0091. PubMed PMID: 26243021. 9: Jiang SK, Zhang M, Tian ZL, Wang M, Zhao R, Wang LL, Li SS, Liu M, Li JY, Zhang MZ, Guan DW. The monoacylglycerol lipase inhibitor JZL184 decreases inflammatory response in skeletal muscle contusion in rats. Eur J Pharmacol. 2015 Aug 15;761:1-10. doi: 10.1016/j.ejphar.2015.04.018. PubMed PMID: 25912803. 10: Gomez O, Sanchez-Rodriguez MA, Ortega-Gutierrez S, Vazquez-Villa H, Guaza C, Molina-Holgado F, Molina-Holgado E. A Basal Tone of 2-Arachidonoylglycerol Contributes to Early Oligodendrocyte Progenitor Proliferation by Activating Phosphatidylinositol 3-Kinase (PI3K)/AKT and the Mammalian Target of Rapamycin (MTOR) Pathways. J Neuroimmune Pharmacol. 2015 Jun;10(2):309-17. doi: 10.1007/s11481-015-9609-x. PubMed PMID: 25900077. 11: Lin TY, Lu CW, Wu CC, Huang SK, Wang SJ. Palmitoylethanolamide inhibits glutamate release in rat cerebrocortical nerve terminals. Int J Mol Sci. 2015 Mar 11;16(3):5555-71. doi: 10.3390/ijms16035555. PubMed PMID: 25768340; PubMed Central PMCID: PMC4394492. 12: Beckley JT, Randall PK, Smith RJ, Hughes BA, Kalivas PW, Woodward JJ. Phenotype-dependent inhibition of glutamatergic transmission on nucleus accumbens medium spiny neurons by the abused inhalant toluene. Addict Biol. 2016 May;21(3):530-46. doi: 10.1111/adb.12235. PubMed PMID: 25752326; PubMed Central PMCID: PMC4561223. 13: Wang TC, Wang J, Xu X, Ma JL, Wang XF. Tonic modulation of nociceptive behavior and allodynia by cannabinoid receptors in formalin test in rats. Chin J Physiol. 2015 Feb 28;58(1):72-8. doi: 10.4077/CJP.2015.BAD307. PubMed PMID: 25687494. 14: Lisboa SF, Gomes FV, Silva AL, Uliana DL, Camargo LH, Guimarães FS, Cunha FQ, Joca SR, Resstel LB. Increased Contextual Fear Conditioning in iNOS Knockout Mice: Additional Evidence for the Involvement of Nitric Oxide in Stress-Related Disorders and Contribution of the Endocannabinoid System. Int J Neuropsychopharmacol. 2015 Jan 24;18(8). pii: pyv005. doi: 10.1093/ijnp/pyv005. PubMed PMID: 25618404; PubMed Central PMCID: PMC4571624. 15: Ladarre D, Roland AB, Biedzinski S, Ricobaraza A, Lenkei Z. Polarized cellular patterns of endocannabinoid production and detection shape cannabinoid signaling in neurons. Front Cell Neurosci. 2015 Jan 6;8:426. doi: 10.3389/fncel.2014.00426. PubMed PMID: 25610369; PubMed Central PMCID: PMC4285097. 16: García-Morales V, Montero F, Moreno-López B. Cannabinoid agonists rearrange synaptic vesicles at excitatory synapses and depress motoneuron activity in vivo. Neuropharmacology. 2015 May;92:69-79. doi: 10.1016/j.neuropharm.2014.12.036. PubMed PMID: 25595101. 17: Mai P, Tian L, Yang L, Wang L, Yang L, Li L. Cannabinoid receptor 1 but not 2 mediates macrophage phagocytosis by G(α)i/o /RhoA/ROCK signaling pathway. J Cell Physiol. 2015 Jul;230(7):1640-50. doi: 10.1002/jcp.24911. PubMed PMID: 25545473. 18: Uhelski ML, Khasabova IA, Simone DA. Inhibition of anandamide hydrolysis attenuates nociceptor sensitization in a murine model of chemotherapy-induced peripheral neuropathy. J Neurophysiol. 2015 Mar 1;113(5):1501-10. doi: 10.1152/jn.00692.2014. PubMed PMID: 25505113; PubMed Central PMCID: PMC4346731. 19: Berger ND, Gadotti VM, Petrov RR, Chapman K, Diaz P, Zamponi GW. NMP-7 inhibits chronic inflammatory and neuropathic pain via block of Cav3.2 T-type calcium channels and activation of CB2 receptors. Mol Pain. 2014 Dec 6;10:77. doi: 10.1186/1744-8069-10-77. PubMed PMID: 25481027; PubMed Central PMCID: PMC4271433. 20: Gasperi V, Evangelista D, Oddi S, Florenzano F, Chiurchiù V, Avigliano L, Catani MV, Maccarrone M. Regulation of inflammation and proliferation of human bladder carcinoma cells by type-1 and type-2 cannabinoid receptors. Life Sci. 2015 Oct 1;138:41-51. doi: 10.1016/j.lfs.2014.09.031. PubMed PMID: 25445433.