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MedKoo Cat#: 592856 | Name: Amphimedine

Description:

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

Amphimedine is a Pyridoacridine Marine Alkaloid.

Chemical Structure

Amphimedine
Amphimedine
CAS#86047-14-5

Theoretical Analysis

MedKoo Cat#: 592856

Name: Amphimedine

CAS#: 86047-14-5

Chemical Formula: C19H11N3O2

Exact Mass: 313.0851

Molecular Weight: 313.32

Elemental Analysis: C, 72.84; H, 3.54; N, 13.41; O, 10.21

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
Amphimedine
IUPAC/Chemical Name
8H-Benzo(b)pyrido(4,3,2-de)(1,8)phenanthroline-8,11(10H)-dione, 10-methyl-
InChi Key
GPJKOFLDDKEODA-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H11N3O2/c1-22-9-13-12(8-15(22)23)17-16-11(6-7-20-18(16)19(13)24)10-4-2-3-5-14(10)21-17/h2-9H,1H3
SMILES Code
O=C(C1=CN2C)C3=C4C(C5=CC=CC=C5N=C4C1=CC2=O)=CC=N3
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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 313.32 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: Khalil IM, Barker D, Copp BR. Bioinspired Syntheses of the Pyridoacridine Marine Alkaloids Demethyldeoxyamphimedine, Deoxyamphimedine, and Amphimedine. J Org Chem. 2016 Jan 4;81(1):282-9. doi: 10.1021/acs.joc.5b02312. Epub 2015 Dec 17. PubMed PMID: 26642369. 2: Sharma V, Sharma PC, Kumar V. A mini review on pyridoacridines: Prospective lead compounds in medicinal chemistry. J Adv Res. 2015 Jan;6(1):63-71. doi: 10.1016/j.jare.2014.11.002. Epub 2014 Nov 15. Review. PubMed PMID: 25685544; PubMed Central PMCID: PMC4293674. 3: Brahic C, Darro F, Belloir M, Bastide J, Kiss R, Delfourne E. Synthesis and cytotoxic evaluation of analogues of the marine pyridoacridine amphimedine. Bioorg Med Chem. 2002 Sep;10(9):2845-53. PubMed PMID: 12110304. 4: Melzer B, Plodek A, Bracher F. Total synthesis of the marine pyridoacridine alkaloid demethyldeoxyamphimedine. J Org Chem. 2014 Aug 1;79(15):7239-42. doi: 10.1021/jo501312d. Epub 2014 Jul 18. PubMed PMID: 25081029. 5: Wei X, Bugni TS, Harper MK, Sandoval IT, Manos EJ, Swift J, Van Wagoner RM, Jones DA, Ireland CM. Evaluation of pyridoacridine alkaloids in a zebrafish phenotypic assay. Mar Drugs. 2010 Jun 2;8(6):1769-78. doi: 10.3390/md8061769. PubMed PMID: 20631869; PubMed Central PMCID: PMC2901824. 6: Marshall KM, Andjelic CD, Tasdemir D, Concepción GP, Ireland CM, Barrows LR. Deoxyamphimedine, a pyridoacridine alkaloid, damages DNA via the production of reactive oxygen species. Mar Drugs. 2009 May 25;7(2):196-209. doi: 10.3390/md7020196. PubMed PMID: 19597581; PubMed Central PMCID: PMC2707043. 7: Marshall KM, Barrows LR. Biological activities of pyridoacridines. Nat Prod Rep. 2004 Dec;21(6):731-51. Epub 2004 Oct 29. Review. PubMed PMID: 15565252. 8: Marshall KM, Matsumoto SS, Holden JA, Concepción GP, Tasdemir D, Ireland CM, Barrows LR. The anti-neoplastic and novel topoisomerase II-mediated cytotoxicity of neoamphimedine, a marine pyridoacridine. Biochem Pharmacol. 2003 Aug 1;66(3):447-58. PubMed PMID: 12907244. 9: Thale Z, Johnson T, Tenney K, Wenzel PJ, Lobkovsky E, Clardy J, Media J, Pietraszkiewicz H, Valeriote FA, Crews P. Structures and cytotoxic properties of sponge-derived bisannulated acridines. J Org Chem. 2002 Dec 27;67(26):9384-91. PubMed PMID: 12492342.