Amodiaquine free base
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MedKoo CAT#: 317185

CAS#: 86-42-0 (free base)

Description: Amodiaquine (trade names Camoquin, Flavoquine), a 4-aminoquinoline compound related to chloroquine, is used as an antimalarial and anti-inflammatory agent. Amodiaquine has been shown to be more effective than chloroquine in treating chloroquine-resistant Plasmodium falciparum malaria infections and may give more protection than chloroquine when used as weekly prophylaxis. Amodiaquine, like chloroquine, is generally well tolerated. Amodiaquine is a histamine N-methyltransferase inhibitor. It is on the World Health Organization's List of Essential Medicines, the most important medications needed in a basic health system.

Chemical Structure

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Amodiaquine free base
CAS# 86-42-0 (free base)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 317185
Name: Amodiaquine free base
CAS#: 86-42-0 (free base)
Chemical Formula: C20H22ClN3O
Exact Mass: 355.15
Molecular Weight: 355.860
Elemental Analysis: C, 67.50; H, 6.23; Cl, 9.96; N, 11.81; O, 4.50

Price and Availability

Size Price Availability Quantity
50mg USD 150 Ready to ship
100mg USD 250 Ready to ship
200mg USD 450 Ready to ship
500mg USD 850 Ready to ship
1g USD 1450 Ready to ship
2g USD 2450 Ready to ship
5g USD 4250 Ready to ship
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Related CAS #: 86-42-0 (free base)   69-44-3 (HCl)   6398-98-7 (HCl hydrate)  

Synonym: Camochin; Camoquin; Camoquinal; Camoquine; Flavoquine; Miaquin; NSC 13453; SN-10751; Amodiaquine free base

IUPAC/Chemical Name: 4-[(7-chloroquinolin-4-yl)amino]-2-(diethylaminomethyl)phenol

InChi Key: OVCDSSHSILBFBN-UHFFFAOYSA-N

InChi Code: InChI=1S/C20H22ClN3O/c1-3-24(4-2)13-14-11-16(6-8-20(14)25)23-18-9-10-22-19-12-15(21)5-7-17(18)19/h5-12,25H,3-4,13H2,1-2H3,(H,22,23)

SMILES Code: CCN(CC)CC1=C(C=CC(=C1)NC2=C3C=CC(=CC3=NC=C2)Cl)O

Appearance: Solid powder

Purity: >95% (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

More Info:

Biological target: Amodiaquine (Amodiaquin), a 4-aminoquinoline class of antimalarial agent, is a potent histamine N-methyltransferase inhibitor and Nurr1 agonist that specifically binds to Nurr1-LBD (ligand binding domain) with an EC50 of ~20 μM.
In vitro activity: Cells treated with 1–10 μM AQ (Amodiaquine) for 6 h accumulated lysosomes (LAMP1-positive puncta) (Fig. 3a, b) while concentrations between 10 and 20 μM further enhanced autophagosome accumulation (Fig. 3c, d; LC3B puncta). Notably, 10–20 μM AQ also induced generation of nucleolar caps (Fig. 3c), showing that both autophagy inhibition and nucleolar stress take place simultaneously. Strikingly, even though AQ and CQ showed similar levels of lipidated LC3 (LC3-II) (Fig. 2a) and accumulation of cytoplasmic vesicles (Fig. 3e), only AQ caused remarkable condensation of nucleolar chromatin (Fig. 3e). Among the 4aminoquinoline family members, CQ and H-CQ inhibit autophagy with efficiency similar to AQ, but RPA194 degradation and p53 stabilization was only induced by AQ (Fig. 3f). Furthermore, only AQ induced a strong reduction of 47S rRNA synthesis among all autophagy inhibitors tested (Fig. 3g). Overall, these findings indicate that ribosome biogenesis stress is not a general consequence of autophagy inhibition and that AQ stands out among the 4-aminoquinoline family as a compound operating through two independent mechanisms: autophagy inhibition in the cytoplasm and ribosome biogenesis stress in the nucleolus. Taken together, the data reveals unsuspected activity of a drug approved and used in the clinics for over 30 years, and provide rationale for repurposing amodiaquine in cancer therapy. Reference: Cell Death Differ. 2020 Feb; 27(2): 773–789. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7205879/
In vivo activity: To confirm the immune suppression by AQ in vivo, mice were fed DSS and intraperitoneally injected with either vehicle or AQ. Body weight loss and colon shortening were induced in the DSS-treated group, but these changes were attenuated in the AQ-treated group (Fig. 7A,B). Histological examination demonstrated that AQ reduced the immune cell infiltration and inhibited epithelial cell destruction with goblet cell depletion in the DSS-induced colitis model (Fig. 7C). Furthermore, T cell-induced colitis in recombinaseactivating gene (RAG) knockout (KO) mice was diminished by administration with AQ, as demonstrated by the decreases in disease activity index and histopathology (Fig. 7D,E). Foxp3+ Treg cells were more frequently found in AQ-treated colon tissues (Fig. 7E). Consistently, AQ administration increased the expression of Foxp3, but decreased the expression of inflammatory markers RORγt and T-bet (Fig. 7F). Moreover, the inflammatory cytokines IL-17 and IFN-γ produced by inflammatory T cells were significantly diminished in the AQ-treated group (Fig. 7G). The ability of anti-malarial AQ to potentiate iTreg cell development makes it a promising drug for preventing and treating inflammatory and autoimmune diseases. Reference: Sci Rep. 2017 Dec 5;7(1):16946. https://pubmed.ncbi.nlm.nih.gov/29208963/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 38.0 106.78
Ethanol 12.0 33.72

Preparing Stock Solutions

The following data is based on the product molecular weight 355.86 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. Won HY, Shin JH, Oh S, Jeong H, Hwang ES. Enhanced CD25+Foxp3+ regulatory T cell development by amodiaquine through activation of nuclear receptor 4A. Sci Rep. 2017 Dec 5;7(1):16946. doi: 10.1038/s41598-017-17073-y. PMID: 29208963; PMCID: PMC5717225. 2. Espinoza JA, Zisi A, Kanellis DC, Carreras-Puigvert J, Henriksson M, Hühn D, Watanabe K, Helleday T, Lindström MS, Bartek J. The antimalarial drug amodiaquine stabilizes p53 through ribosome biogenesis stress, independently of its autophagy-inhibitory activity. Cell Death Differ. 2020 Feb;27(2):773-789. doi: 10.1038/s41418-019-0387-5. Epub 2019 Jul 8. PMID: 31285544; PMCID: PMC7205879. 3. DeWald LE, Johnson JC, Gerhardt DM, Torzewski LM, Postnikova E, Honko AN, Janosko K, Huzella L, Dowling WE, Eakin AE, Osborn BL, Gahagen J, Tang L, Green CE, Mirsalis JC, Holbrook MR, Jahrling PB, Dyall J, Hensley LE. In Vivo Activity of Amodiaquine against Ebola Virus Infection. Sci Rep. 2019 Dec 27;9(1):20199. doi: 10.1038/s41598-019-56481-0. PMID: 31882748; PMCID: PMC6934550.
In vitro protocol: 1. Won HY, Shin JH, Oh S, Jeong H, Hwang ES. Enhanced CD25+Foxp3+ regulatory T cell development by amodiaquine through activation of nuclear receptor 4A. Sci Rep. 2017 Dec 5;7(1):16946. doi: 10.1038/s41598-017-17073-y. PMID: 29208963; PMCID: PMC5717225. 2. Espinoza JA, Zisi A, Kanellis DC, Carreras-Puigvert J, Henriksson M, Hühn D, Watanabe K, Helleday T, Lindström MS, Bartek J. The antimalarial drug amodiaquine stabilizes p53 through ribosome biogenesis stress, independently of its autophagy-inhibitory activity. Cell Death Differ. 2020 Feb;27(2):773-789. doi: 10.1038/s41418-019-0387-5. Epub 2019 Jul 8. PMID: 31285544; PMCID: PMC7205879.
In vivo protocol: 1. Won HY, Shin JH, Oh S, Jeong H, Hwang ES. Enhanced CD25+Foxp3+ regulatory T cell development by amodiaquine through activation of nuclear receptor 4A. Sci Rep. 2017 Dec 5;7(1):16946. doi: 10.1038/s41598-017-17073-y. PMID: 29208963; PMCID: PMC5717225. 2. DeWald LE, Johnson JC, Gerhardt DM, Torzewski LM, Postnikova E, Honko AN, Janosko K, Huzella L, Dowling WE, Eakin AE, Osborn BL, Gahagen J, Tang L, Green CE, Mirsalis JC, Holbrook MR, Jahrling PB, Dyall J, Hensley LE. In Vivo Activity of Amodiaquine against Ebola Virus Infection. Sci Rep. 2019 Dec 27;9(1):20199. doi: 10.1038/s41598-019-56481-0. PMID: 31882748; PMCID: PMC6934550.

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18: DeWald LE, Johnson JC, Gerhardt DM, Torzewski LM, Postnikova E, Honko AN, Janosko K, Huzella L, Dowling WE, Eakin AE, Osborn BL, Gahagen J, Tang L, Green CE, Mirsalis JC, Holbrook MR, Jahrling PB, Dyall J, Hensley LE. In Vivo Activity of Amodiaquine against Ebola Virus Infection. Sci Rep. 2019 Dec 27;9(1):20199. doi: 10.1038/s41598-019-56481-0. PMID: 31882748; PMCID: PMC6934550.


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