MedKoo Cat#: 413992 | Name: Echitamine Free Base

Description:

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

Echitamine Free Base is a natural indole alkaloid found in the herbs of Alstonia scholaris, exhibits the anti-tumour activity in-vitro and in-vivo

Chemical Structure

Echitamine Free Base
Echitamine Free Base
CAS#6871-44-9 (free base)

Theoretical Analysis

MedKoo Cat#: 413992

Name: Echitamine Free Base

CAS#: 6871-44-9 (free base)

Chemical Formula: C22H29N2O4+

Exact Mass: 385.2122

Molecular Weight: 385.48

Elemental Analysis: C, 68.55; H, 7.58; N, 7.27; O, 16.60

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 #
464-20-0 (hydroxide) 6871-44-9 (free) 6878-36-0 (chloride)
Synonym
Echitamine Free Base; BRN4164538; BRN-4164538; BRN 4164538
IUPAC/Chemical Name
(1S,3S,6S,8aS,13aR,14R,E)-4-ethylidene-1-hydroxy-14-(hydroxymethyl)-14-(methoxycarbonyl)-6-methyl-1,2,3,4,5,6,7,8-octahydro-13H-3,8a-methanoazepino[1',2':1,2]pyrrolo[2,3-b]indol-6-ium
InChi Key
AFJPGVUCVDCFPM-BBFZNYENSA-N
InChi Code
InChI=1S/C22H29N2O4/c1-4-14-12-24(2)10-9-21-15-7-5-6-8-17(15)23-22(21,24)18(26)11-16(14)20(21,13-25)19(27)28-3/h4-8,16,18,23,25-26H,9-13H2,1-3H3/q+1/b14-4-/t16-,18-,20-,21-,22-,24-/m0/s1
SMILES Code
COC([C@@]1([C@H]2C[C@@H]([C@@]34Nc5c([C@@]13CC[N@+]4(C/C2=C/C)C)cccc5)O)CO)=O
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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 385.48 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: Zhang X, Kakde BN, Guo R, Yadav S, Gu Y, Li A. Total Syntheses of Echitamine, Akuammiline, Rhazicine, and Pseudoakuammigine. Angew Chem Int Ed Engl. 2019 Apr 23;58(18):6053-6058. doi: 10.1002/anie.201901086. Epub 2019 Mar 27. PMID: 30803132. 2: George G, P S D, Paul AT. Development and validation of a new HPTLC-HRMS method for the quantification of a potent pancreatic lipase inhibitory lead Echitamine from Alstonia scholaris. Nat Prod Res. 2019 Dec 24:1-5. doi: 10.1080/14786419.2019.1705817. Epub ahead of print. PMID: 31872775. 3: Saraswathi V, Ramamoorthy N, Subramaniam S, Mathuram V, Gunasekaran P, Govindasamy S. Inhibition of glycolysis and respiration of sarcoma-180 cells by echitamine chloride. Chemotherapy. 1998 May-Jun;44(3):198-205. doi: 10.1159/000007115. PMID: 9612610. 4: Jagetia GC, Baliga MS, Venkatesh P, Ulloor JN, Mantena SK, Genebriera J, Mathuram V. Evaluation of the cytotoxic effect of the monoterpene indole alkaloid echitamine in-vitro and in tumour-bearing mice. J Pharm Pharmacol. 2005 Sep;57(9):1213-9. doi: 10.1211/jpp.57.9.0017. PMID: 16105243. 5: Wright CW, Allen D, Phillipson JD, Kirby GC, Warhurst DC, Massiot G, Le Men- Olivier L. Alstonia species: are they effective in malaria treatment? J Ethnopharmacol. 1993 Sep;40(1):41-5. doi: 10.1016/0378-8741(93)90087-l. PMID: 8246529. 6: Cimanga RK, Nsaka SL, Tshodi ME, Mbamu BM, Kikweta CM, Makila FB, Cos P, Maes L, Vlietinck AJ, Exarchou V, Tuenter E, Pieters L. In vitro and in vivo antiplasmodial activity of extracts and isolated constituents of Alstonia congensis root bark. J Ethnopharmacol. 2019 Oct 5;242:111736. doi: 10.1016/j.jep.2019.02.019. Epub 2019 Feb 11. PMID: 30763695. 7: Adams GL, Smith AB 3rd. The Chemistry of the Akuammiline Alkaloids. Alkaloids Chem Biol. 2016;76:171-257. doi: 10.1016/bs.alkal.2015.08.001. Epub 2015 Sep 26. PMID: 26827884. 8: Saraswathi V, Mathuram V, Subramanian S, Govindasamy S. Modulation of the impaired drug metabolism in sarcoma-180-bearing mice by echitamine chloride. Cancer Biochem Biophys. 1999 Jul;17(1-2):79-88. PMID: 10738904. 9: Manjeshwar Shrinath Baliga. Alstonia scholaris Linn R Br in the treatment and prevention of cancer: past, present, and future. Integr Cancer Ther. 2010 Sep;9(3):261-9. doi: 10.1177/1534735410376068. Epub 2010 Aug 11. PMID: 20702494. 10: Ramírez A, García-Rubio S. Current progress in the chemistry and pharmacology of akuammiline alkaloids. Curr Med Chem. 2003 Sep;10(18):1891-915. doi: 10.2174/0929867033457016. PMID: 12871110.