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MedKoo Cat#: 591001 | Name: Mepacrine

Description:

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

Mepacrine is an acridine derivative formerly widely used as an antimalarial but superseded by chloroquine in recent years. It has also been used as an anthelmintic and in the treatment of giardiasis and malignant effusions. It is used in cell biological experiments as an inhibitor of phospholipase A2.

Chemical Structure

Mepacrine
Mepacrine
CAS#83-89-6

Theoretical Analysis

MedKoo Cat#: 591001

Name: Mepacrine

CAS#: 83-89-6

Chemical Formula: C23H30ClN30

Exact Mass: 399.2077

Molecular Weight: 399.21

Elemental Analysis: C, 69.07; H, 7.56; Cl, 8.86; N, 10.51; O, 4.00

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Erion; Haffkinine
IUPAC/Chemical Name
Acridine, 6-chloro-9-((4-(diethylamino)-1-methylbutyl)amino)-2-methoxy-
InChi Key
GPKJTRJOBQGKQK-UHFFFAOYSA-N
InChi Code
InChI=1S/C23H30ClN3O/c1-5-27(6-2)13-7-8-16(3)25-23-19-11-9-17(24)14-22(19)26-21-12-10-18(28-4)15-20(21)23/h9-12,14-16H,5-8,13H2,1-4H3,(H,25,26)
SMILES Code
COC1=CC2=C(NC(C)CCCN(CC)CC)C3=CC=C(Cl)C=C3N=C2C=C1
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

Preparing Stock Solutions

The following data is based on the product molecular weight 399.21 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
1: Park S, Oh AY, Cho JH, Yoon MH, Woo TG, Kang SM, Lee HY, Jung YJ, Park BJ. Therapeutic Effect of Quinacrine, an Antiprotozoan Drug, by Selective Suppression of p-CHK1/2 in p53-Negative Malignant Cancers. Mol Cancer Res. 2018 Mar 15. doi: 10.1158/1541-7786.MCR-17-0511. [Epub ahead of print] PubMed PMID: 29545477. 2: Abdulaziz N, Shah AR, McCune WJ. Hydroxychloroquine: balancing the need to maintain therapeutic levels with ocular safety: an update. Curr Opin Rheumatol. 2018 May;30(3):249-255. doi: 10.1097/BOR.0000000000000500. PubMed PMID: 29517495. 3: Jung D, Khurana A, Roy D, Kalogera E, Bakkum-Gamez J, Chien J, Shridhar V. Quinacrine upregulates p21/p27 independent of p53 through autophagy-mediated downregulation of p62-Skp2 axis in ovarian cancer. Sci Rep. 2018 Feb 6;8(1):2487. doi: 10.1038/s41598-018-20531-w. PubMed PMID: 29410485; PubMed Central PMCID: PMC5802832. 4: Nicastri MC, Rebecca VW, Amaravadi RK, Winkler JD. Dimeric quinacrines as chemical tools to identify PPT1, a new regulator of autophagy in cancer cells. Mol Cell Oncol. 2017 Nov 30;5(1):e1395504. doi: 10.1080/23723556.2017.1395504. eCollection 2018. PubMed PMID: 29404393; PubMed Central PMCID: PMC5791860. 5: Zhu S, Chen Z, Wang L, Peng D, Belkhiri A, Lockhart AC, El-Rifai W. A Combination of SAHA and Quinacrine Is Effective in Inducing Cancer Cell Death in Upper Gastrointestinal Cancers. Clin Cancer Res. 2018 Apr 15;24(8):1905-1916. doi: 10.1158/1078-0432.CCR-17-1716. Epub 2018 Jan 31. PubMed PMID: 29386219. 6: Yan H, Bian A, Gao X, Li H, Chen Z, Liu X. Novel applications for an established antimalarial drug: tumoricidal activity of quinacrine. Future Oncol. 2018 Jan 30. doi: 10.2217/fon-2017-0728. [Epub ahead of print] PubMed PMID: 29380639. 7: Satapathy SR, Nayak A, Siddharth S, Das S, Nayak D, Kundu CN. Metallic gold and bioactive quinacrine hybrid nanoparticles inhibit oral cancer stem cell and angiogenesis by deregulating inflammatory cytokines in p53 dependent manner. Nanomedicine. 2018 Apr;14(3):883-896. doi: 10.1016/j.nano.2018.01.007. Epub 2018 Jan 31. PubMed PMID: 29366881. 8: Solomon VR, Pundir S, Le HT, Lee H. Design and synthesis of novel quinacrine-[1,3]-thiazinan-4-one hybrids for their anti-breast cancer activity. Eur J Med Chem. 2018 Jan 1;143:1028-1038. doi: 10.1016/j.ejmech.2017.11.097. PubMed PMID: 29232580. 9: Andres O, Henning K, Strauß G, Pflug A, Manukjan G, Schulze H. Diagnosis of platelet function disorders: A standardized, rational, and modular flow cytometric approach. Platelets. 2018 Jun;29(4):347-356. doi: 10.1080/09537104.2017.1386297. Epub 2017 Dec 11. PubMed PMID: 29227167. 10: Harada M, Morimoto K, Kondo T, Hiramatsu R, Okina Y, Muko R, Matsuda I, Kataoka T. Quinacrine Inhibits ICAM-1 Transcription by Blocking DNA Binding of the NF-κB Subunit p65 and Sensitizes Human Lung Adenocarcinoma A549 Cells to TNF-α and the Fas Ligand. Int J Mol Sci. 2017 Dec 2;18(12). pii: E2603. doi: 10.3390/ijms18122603. PubMed PMID: 29207489; PubMed Central PMCID: PMC5751206. 11: Yang S, Sheng L, Xu K, Wang Y, Zhu H, Zhang P, Mu Q, Ouyang G. Anticancer effect of quinacrine on diffuse large B cell lymphoma via inhibition of MSI2 NUMB signaling pathway. Mol Med Rep. 2018 Jan;17(1):522-530. doi: 10.3892/mmr.2017.7892. Epub 2017 Oct 26. PubMed PMID: 29115587. 12: Eriksson A, Chantzi E, Fryknäs M, Gullbo J, Nygren P, Gustafsson M, Höglund M, Larsson R. Towards repositioning of quinacrine for treatment of acute myeloid leukemia - Promising synergies and in vivo effects. Leuk Res. 2017 Dec;63:41-46. doi: 10.1016/j.leukres.2017.10.012. Epub 2017 Oct 28. PubMed PMID: 29100024. 13: Maletzki C, Rosche Y, Riess C, Scholz A, William D, Classen CF, Kreikemeyer B, Linnebacher M, Fiedler T. Deciphering molecular mechanisms of arginine deiminase-based therapy - Comparative response analysis in paired human primary and recurrent glioblastomas. Chem Biol Interact. 2017 Dec 25;278:179-188. doi: 10.1016/j.cbi.2017.10.007. Epub 2017 Oct 5. PubMed PMID: 28989041. 14: Bhateja P, Dowlati A, Sharma N. Phase I study of the combination of quinacrine and erlotinib in patients with locally advanced or metastatic non small cell lung cancer. Invest New Drugs. 2018 Jun;36(3):435-441. doi: 10.1007/s10637-017-0515-3. Epub 2017 Oct 2. PubMed PMID: 28971268. 15: Alves P, Bashir MM, Wysocka M, Zeidi M, Feng R, Werth VP. Quinacrine Suppresses Tumor Necrosis Factor-α and IFN-α in Dermatomyositis and Cutaneous Lupus Erythematosus. J Investig Dermatol Symp Proc. 2017 Oct;18(2):S57-S63. doi: 10.1016/j.jisp.2016.11.001. Review. PubMed PMID: 28941496; PubMed Central PMCID: PMC5645024. 16: Das S, Nayak A, Siddharth S, Nayak D, Narayan S, Kundu CN. TRAIL enhances quinacrine-mediated apoptosis in breast cancer cells through induction of autophagy via modulation of p21 and DR5 interactions. Cell Oncol (Dordr). 2017 Dec;40(6):593-607. doi: 10.1007/s13402-017-0347-3. Epub 2017 Sep 21. PubMed PMID: 28936683. 17: Rebecca VW, Nicastri MC, McLaughlin N, Fennelly C, McAfee Q, Ronghe A, Nofal M, Lim CY, Witze E, Chude CI, Zhang G, Alicea GM, Piao S, Murugan S, Ojha R, Levi SM, Wei Z, Barber-Rotenberg JS, Murphy ME, Mills GB, Lu Y, Rabinowitz J, Marmorstein R, Liu Q, Liu S, Xu X, Herlyn M, Zoncu R, Brady DC, Speicher DW, Winkler JD, Amaravadi RK. A Unified Approach to Targeting the Lysosome's Degradative and Growth Signaling Roles. Cancer Discov. 2017 Nov;7(11):1266-1283. doi: 10.1158/2159-8290.CD-17-0741. Epub 2017 Sep 12. PubMed PMID: 28899863; PubMed Central PMCID: PMC5833978. 18: Huang CH, Lee YC, Chen YJ, Wang LJ, Shi YJ, Chang LS. Quinacrine induces the apoptosis of human leukemia U937 cells through FOXP3/miR-183/β-TrCP/SP1 axis-mediated BAX upregulation. Toxicol Appl Pharmacol. 2017 Nov 1;334:35-46. doi: 10.1016/j.taap.2017.08.019. Epub 2017 Sep 1. PubMed PMID: 28867437. 19: Yamazaki S, Diaz MA, Carlino TM, Gotluru C, Mazza MMA, Scott AM. Ultrafast Spectroscopic Dynamics of Quinacrine-Riboflavin Binding Protein Interactions. J Phys Chem B. 2017 Sep 7;121(35):8291-8299. doi: 10.1021/acs.jpcb.7b05304. Epub 2017 Aug 29. PubMed PMID: 28762739. 20: Nayak A, Siddharth S, Das S, Nayak D, Sethy C, Kundu CN. Nanoquinacrine caused apoptosis in oral cancer stem cells by disrupting the interaction between GLI1 and β catenin through activation of GSK3β. Toxicol Appl Pharmacol. 2017 Sep 1;330:53-64. doi: 10.1016/j.taap.2017.07.008. Epub 2017 Jul 15. PubMed PMID: 28720477.