AM4113
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MedKoo CAT#: 525320

CAS#: 614726-85-1

Description: AM4113 is a cannabinoid receptor 1 (CB1)-selective antagonist. AM4113 reverts the effects of cannabidiol on cue and stress-induced reinstatement of cocaine-seeking behaviour in mice. AM4113 inhibits heroin self-administration without depressive side effects in rat. AM4113 Retains the Therapeutic Efficacy of the Inverse Agonist Rimonabant for Nicotine Dependence and Weight Loss with Better Psychiatric Tolerability

Chemical Structure

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AM4113
CAS# 614726-85-1
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 525320
Name: AM4113
CAS#: 614726-85-1
Chemical Formula: C17H12Cl3N3O
Exact Mass: 379.00
Molecular Weight: 380.653
Elemental Analysis: C, 53.64; H, 3.18; Cl, 27.94; N, 11.04; O, 4.20

Price and Availability

Size Price Availability Quantity
50mg USD 750 2 Weeks
100mg USD 1250 2 Weeks
200mg USD 2250 2 Weeks
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Synonym: AM4113; AM-4113; AM 4113;

IUPAC/Chemical Name: 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methylpyrazole-3-carboxamide

InChi Key: BBUKVPCUOHFAQN-UHFFFAOYSA-N

InChi Code: InChI=1S/C17H12Cl3N3O/c1-9-15(17(21)24)22-23(14-7-6-12(19)8-13(14)20)16(9)10-2-4-11(18)5-3-10/h2-8H,1H3,(H2,21,24)

SMILES Code: O=C(C1=NN(C2=CC=C(Cl)C=C2Cl)C(C3=CC=C(Cl)C=C3)=C1C)N

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: CB1 antagonist 2 inhibits CB1 in vivo with an IC50 of 25.5 nM.
In vitro activity: TBD
In vivo activity: AM4113 (10 mg kg−1) significantly reduced food intake in wild type mice, F=13.6, p=0.006 (Figure 1A), at 2, 3 and 18 h, p<0.05. In comparison, there were no significant differences in food intake between vehicle and AM4113 treated CB1 receptor knockout mice, F=0.6, p>0.05 (Figure 1B). Reference: Pharmacol Biochem Behav. 2011 Jan 1; 97(3): 537–543. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3023913/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 24.4 64.02
DMF 10.0 26.27
DMF:PBS (pH 7.2) (1:3) 0.3 0.66
Ethanol 4.1 10.67

Preparing Stock Solutions

The following data is based on the product molecular weight 380.65 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. He XH, Jordan CJ, Vemuri K, Bi GH, Zhan J, Gardner EL, Makriyannis A, Wang YL, Xi ZX. Cannabinoid CB1 receptor neutral antagonist AM4113 inhibits heroin self-administration without depressive side effects in rats. Acta Pharmacol Sin. 2019 Mar;40(3):365-373. doi: 10.1038/s41401-018-0059-x. Epub 2018 Jul 2. PMID: 29967454; PMCID: PMC6460369. 2. Cluny NL, Chambers AP, Vemuri VK, Wood JT, Eller LK, Freni C, Reimer RA, Makriyannis A, Sharkey KA. The neutral cannabinoid CB₁ receptor antagonist AM4113 regulates body weight through changes in energy intake in the rat. Pharmacol Biochem Behav. 2011 Jan;97(3):537-43. doi: 10.1016/j.pbb.2010.10.013. Epub 2010 Nov 4. PMID: 21056053; PMCID: PMC3023913.
In vitro protocol: TBD
In vivo protocol: 1. He XH, Jordan CJ, Vemuri K, Bi GH, Zhan J, Gardner EL, Makriyannis A, Wang YL, Xi ZX. Cannabinoid CB1 receptor neutral antagonist AM4113 inhibits heroin self-administration without depressive side effects in rats. Acta Pharmacol Sin. 2019 Mar;40(3):365-373. doi: 10.1038/s41401-018-0059-x. Epub 2018 Jul 2. PMID: 29967454; PMCID: PMC6460369. 2. Cluny NL, Chambers AP, Vemuri VK, Wood JT, Eller LK, Freni C, Reimer RA, Makriyannis A, Sharkey KA. The neutral cannabinoid CB₁ receptor antagonist AM4113 regulates body weight through changes in energy intake in the rat. Pharmacol Biochem Behav. 2011 Jan;97(3):537-43. doi: 10.1016/j.pbb.2010.10.013. Epub 2010 Nov 4. PMID: 21056053; PMCID: PMC3023913.

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1: Luján MÁ, Alegre-Zurano L, Martín-Sánchez A, Cantacorps L, Valverde O. CB1 receptor antagonist AM4113 reverts the effects of cannabidiol on cue and stress- induced reinstatement of cocaine-seeking behaviour in mice. Prog Neuropsychopharmacol Biol Psychiatry. 2022 Mar 8;113:110462. doi: 10.1016/j.pnpbp.2021.110462. Epub 2021 Oct 22. PMID: 34688811.


2: Sepulveda DE, Morris DP, Raup-Konsavage WM, Sun D, Vrana KE, Graziane NM. Cannabigerol (CBG) attenuates mechanical hypersensitivity elicited by chemotherapy-induced peripheral neuropathy. Eur J Pain. 2022 Oct;26(9):1950-1966. doi: 10.1002/ejp.2016. Epub 2022 Aug 4. PMID: 35899583.


3: AlKhelb D, Kirunda A, Ho TC, Makriyannis A, Desai RI. Effects of the cannabinoid CB1-receptor neutral antagonist AM4113 and antagonist/inverse agonist rimonabant on fentanyl discrimination in male rats. Drug Alcohol Depend. 2022 Nov 1;240:109646. doi: 10.1016/j.drugalcdep.2022.109646. Epub 2022 Sep 26. PMID: 36191533.


4: He XH, Jordan CJ, Vemuri K, Bi GH, Zhan J, Gardner EL, Makriyannis A, Wang YL, Xi ZX. Cannabinoid CB1 receptor neutral antagonist AM4113 inhibits heroin self-administration without depressive side effects in rats. Acta Pharmacol Sin. 2019 Mar;40(3):365-373. doi: 10.1038/s41401-018-0059-x. Epub 2018 Jul 2. PMID: 29967454; PMCID: PMC6460369.


5: Järbe TU, LeMay BJ, Olszewska T, Vemuri VK, Wood JT, Makriyannis A. Intrinsic effects of AM4113, a putative neutral CB1 receptor selective antagonist, on open-field behaviors in rats. Pharmacol Biochem Behav. 2008 Nov;91(1):84-90. doi: 10.1016/j.pbb.2008.06.014. Epub 2008 Jun 29. PMID: 18640150; PMCID: PMC2630887.


6: Eid BG, Neamatallah T, Hanafy A, El-Bassossy HM, Binmahfouz L, Aldawsari HM, Hasan A, El-Aziz GA, Vemuri K, Makriyannis A. Interference with TGFβ1-Mediated Inflammation and Fibrosis Underlies Reno-Protective Effects of the CB1 Receptor Neutral Antagonists AM6545 and AM4113 in a Rat Model of Metabolic Syndrome. Molecules. 2021 Feb 6;26(4):866. doi: 10.3390/molecules26040866. PMID: 33562080; PMCID: PMC7914730.


7: Eid BG, Neamatallah T, Hanafy A, El-Bassossy HM, Aldawsari HM, Vemuri K, Makriyannis A. Effects of the CB1 Receptor Antagonists AM6545 and AM4113 on Insulin Resistance in a High-Fructose High-Salt Rat Model of Metabolic Syndrome. Medicina (Kaunas). 2020 Oct 29;56(11):573. doi: 10.3390/medicina56110573. PMID: 33138155; PMCID: PMC7692885.


8: Gueye AB, Pryslawsky Y, Trigo JM, Poulia N, Delis F, Antoniou K, Loureiro M, Laviolette SR, Vemuri K, Makriyannis A, Le Foll B. The CB1 Neutral Antagonist AM4113 Retains the Therapeutic Efficacy of the Inverse Agonist Rimonabant for Nicotine Dependence and Weight Loss with Better Psychiatric Tolerability. Int J Neuropsychopharmacol. 2016 Dec 30;19(12):pyw068. doi: 10.1093/ijnp/pyw068. PMID: 27493155; PMCID: PMC5203757.


9: Cluny NL, Chambers AP, Vemuri VK, Wood JT, Eller LK, Freni C, Reimer RA, Makriyannis A, Sharkey KA. The neutral cannabinoid CB₁ receptor antagonist AM4113 regulates body weight through changes in energy intake in the rat. Pharmacol Biochem Behav. 2011 Jan;97(3):537-43. doi: 10.1016/j.pbb.2010.10.013. Epub 2010 Nov 4. PMID: 21056053; PMCID: PMC3023913.


10: Sink KS, McLaughlin PJ, Wood JA, Brown C, Fan P, Vemuri VK, Peng Y, Olszewska T, Thakur GA, Makriyannis A, Parker LA, Salamone JD. The novel cannabinoid CB1 receptor neutral antagonist AM4113 suppresses food intake and food-reinforced behavior but does not induce signs of nausea in rats. Neuropsychopharmacology. 2008 Mar;33(4):946-55. doi: 10.1038/sj.npp.1301476. Epub 2007 Jun 20. Erratum in: Neuropsychopharmacology. 2008 Jun;33(7):1776. Pang, Yan [corrected to Peng, Yan]; Olzewska, Teresa [corrected to Olszewska, Teresa]. PMID: 17581535; PMCID: PMC3711240.


11: Eid BG, Neamatallah T, Binmahfouz LS, Bagher AM, Alamoudi AJ, Aldawsari HM, Hanafy A, Hasan A, El-Bassossy HM, Abdel-Naim AB, Vemuri K, Makriyannis A. Effects of the CB1 receptor antagonists AM6545 and AM4113 on metabolic syndrome- induced prostatic hyperplasia in rats. Biomol Biomed. 2023 May 19. doi: 10.17305/bb.2023.9173. Epub ahead of print. PMID: 37212036.


12: Chambers AP, Vemuri VK, Peng Y, Wood JT, Olszewska T, Pittman QJ, Makriyannis A, Sharkey KA. A neutral CB1 receptor antagonist reduces weight gain in rat. Am J Physiol Regul Integr Comp Physiol. 2007 Dec;293(6):R2185-93. doi: 10.1152/ajpregu.00663.2007. Epub 2007 Oct 24. PMID: 17959701.


13: Sink KS, Vemuri VK, Wood J, Makriyannis A, Salamone JD. Oral bioavailability of the novel cannabinoid CB1 antagonist AM6527: effects on food-reinforced behavior and comparisons with AM4113. Pharmacol Biochem Behav. 2009 Jan;91(3):303-6. doi: 10.1016/j.pbb.2008.07.013. Epub 2008 Jul 24. PMID: 18703081; PMCID: PMC2806679.


14: Sink KS, Segovia KN, Sink J, Randall PA, Collins LE, Correa M, Markus EJ, Vemuri VK, Makriyannis A, Salamone JD. Potential anxiogenic effects of cannabinoid CB1 receptor antagonists/inverse agonists in rats: comparisons between AM4113, AM251, and the benzodiazepine inverse agonist FG-7142. Eur Neuropsychopharmacol. 2010 Feb;20(2):112-22. doi: 10.1016/j.euroneuro.2009.11.002. Epub 2009 Dec 16. PMID: 20015619; PMCID: PMC2817975.


15: Schindler CW, Redhi GH, Vemuri K, Makriyannis A, Le Foll B, Bergman J, Goldberg SR, Justinova Z. Blockade of Nicotine and Cannabinoid Reinforcement and Relapse by a Cannabinoid CB1-Receptor Neutral Antagonist AM4113 and Inverse Agonist Rimonabant in Squirrel Monkeys. Neuropsychopharmacology. 2016 Aug;41(9):2283-93. doi: 10.1038/npp.2016.27. Epub 2016 Feb 18. PMID: 26888056; PMCID: PMC4946059.


16: Sink KS, Segovia KN, Nunes EJ, Collins LE, Vemuri VK, Thakur G, Makriyannis A, Salamone JD. Intracerebroventricular administration of cannabinoid CB1 receptor antagonists AM251 and AM4113 fails to alter food-reinforced behavior in rats. Psychopharmacology (Berl). 2009 Oct;206(2):223-32. doi: 10.1007/s00213-009-1602-8. Epub 2009 Jul 10. PMID: 19588124; PMCID: PMC4425366.


17: Sink KS, Segovia KN, Collins LE, Markus EJ, Vemuri VK, Makriyannis A, Salamone JD. The CB1 inverse agonist AM251, but not the CB1 antagonist AM4113, enhances retention of contextual fear conditioning in rats. Pharmacol Biochem Behav. 2010 Jun;95(4):479-84. doi: 10.1016/j.pbb.2010.03.011. Epub 2010 Mar 27. PMID: 20347865; PMCID: PMC5441522.


18: Bergman J, Delatte MS, Paronis CA, Vemuri K, Thakur GA, Makriyannis A. Some effects of CB1 antagonists with inverse agonist and neutral biochemical properties. Physiol Behav. 2008 Mar 18;93(4-5):666-70. doi: 10.1016/j.physbeh.2007.11.007. Epub 2007 Nov 12. PMID: 18076956; PMCID: PMC2441972.


19: Wills KL, Vemuri K, Kalmar A, Lee A, Limebeer CL, Makriyannis A, Parker LA. CB1 antagonism: interference with affective properties of acute naloxone- precipitated morphine withdrawal in rats. Psychopharmacology (Berl). 2014 Nov;231(22):4291-300. doi: 10.1007/s00213-014-3575-5. Epub 2014 Apr 27. Erratum in: Psychopharmacology (Berl). 2014 Nov;231(22):4419-20. PMID: 24770676; PMCID: PMC4209202.


20: Balla A, Dong B, Shilpa BM, Vemuri K, Makriyannis A, Pandey SC, Sershen H, Suckow RF, Vinod KY. Cannabinoid-1 receptor neutral antagonist reduces binge- like alcohol consumption and alcohol-induced accumbal dopaminergic signaling. Neuropharmacology. 2018 Mar 15;131:200-208. doi: 10.1016/j.neuropharm.2017.10.040. Epub 2017 Nov 3. PMID: 29109060; PMCID: PMC5820178.