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MedKoo Cat#: 146077 | Name: Erythraline

Description:

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

Erythraline is an alkaloid compound derived from certain plant species, primarily known for its potential therapeutic applications. It has shown promise in the treatment of various conditions, including its use as an antimicrobial and antimalarial agent. The mechanism of erythraline involves the inhibition of key enzymes or disruption of cellular processes in pathogens, leading to their death or inhibited growth. Though not widely used in modern clinical practice, its biological activity continues to be studied for potential applications in drug development, particularly in treating infections.

Chemical Structure

Erythraline
Erythraline
CAS#466-77-3

Theoretical Analysis

MedKoo Cat#: 146077

Name: Erythraline

CAS#: 466-77-3

Chemical Formula: C18H19NO3

Exact Mass: 297.1365

Molecular Weight: 297.35

Elemental Analysis: C, 72.71; H, 6.44; N, 4.71; O, 16.14

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
Erythraline; Erythralin;
IUPAC/Chemical Name
(2R,14bS)-2-methoxy-2,6,8,9-tetrahydro-1H-[1,3]dioxolo[4,5-g]indolo[7a,1-a]isoquinoline
InChi Key
TVOFUERNMZTYRM-KSSFIOAISA-N
InChi Code
1S/C18H19NO3/c1-20-14-3-2-13-5-7-19-6-4-12-8-16-17(22-11-21-16)9-15(12)18(13,19)10-14/h2-3,5,8-9,14H,4,6-7,10-11H2,1H3/t14-,18-/m0/s1
SMILES Code
CO[C@@H]1C[C@]23N(CC=C2C=C1)CCC4=C3C=C5OCOC5=C4
Appearance
To be determined
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 297.35 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: Guaratini T, Silva DB, Bizaro AC, Sartori LR, Humpf HU, Lopes NP, Costa- Lotufo LV, Lopes JL. In vitro metabolism studies of erythraline, the major spiroalkaloid from Erythrina verna. BMC Complement Altern Med. 2014 Feb 18;14:61. doi: 10.1186/1472-6882-14-61. PMID: 24548728; PMCID: PMC3930555. 2: Etoh T, Kim YP, Ohsaki A, Komiyama K, Hayashi M. Inhibitory effect of erythraline on Toll-like receptor signaling pathway in RAW264.7 cells. Biol Pharm Bull. 2013;36(8):1363-9. doi: 10.1248/bpb.b12-00910. PMID: 23902980. 3: Umihara H, Yoshino T, Shimokawa J, Kitamura M, Fukuyama T. Development of a Divergent Synthetic Route to the Erythrina Alkaloids: Asymmetric Syntheses of 8-Oxo-erythrinine, Crystamidine, 8-Oxo-erythraline, and Erythraline. Angew Chem Int Ed Engl. 2016 Jun 6;55(24):6915-8. doi: 10.1002/anie.201602650. Epub 2016 May 4. PMID: 27145193. 4: Cai YS, Li Y, Chen ZC, Yu SS. [Erythrina alkaloids from stems of Erythrina corallodendron]. Zhongguo Zhong Yao Za Zhi. 2021 Jul;46(13):3368-3376. Chinese. doi: 10.19540/j.cnki.cjcmm.20210331.201. PMID: 34396757. 5: de Almeida WAM, de Andrade JP, Chacon DS, Lucas CR, Mariana E, de Santis Ferreira L, Guaratini T, Barbosa EG, Zuanazzi JA, Hallwass F, de Souza Borges W, de Paula Oliveira R, Giordani RB. Isoquinoline alkaloids reduce beta-amyloid peptide toxicity in Caenorhabditis elegans. Nat Prod Res. 2021 Nov;35(22):4814-4818. doi: 10.1080/14786419.2020.1727471. Epub 2020 Feb 18. PMID: 32067490. 6: Maier UH, Rödl W, Deus-Neumann B, Zenk MH. Biosynthesis of Erythrina alkaloids in Erythrina crista-galli. Phytochemistry. 1999 Oct;52(3):373-82. doi: 10.1016/s0031-9422(99)00230-7. PMID: 10501023. 7: Silva DB, Guaratini T, Vessecchi R, Lopes NP, Cramer B, Humpf HU, Lopes JL. H2 unimolecular elimination in electrospray ionization mass spectrometry from erythraline, a spirocyclic alkaloid. Eur J Mass Spectrom (Chichester). 2013;19(5):345-50. doi: 10.1255/ejms.1243. PMID: 24800418. 8: Garín-Aguilar ME, Valencia del Toro G, Soto-Hernández M, Kite G. High- performance liquid chromatography-mass spectrometric analysis of alkaloids extracted from seeds of Erythrina herbacea. Phytochem Anal. 2005 Sep- Oct;16(5):302-6. doi: 10.1002/pca.821. PMID: 16223085. 9: Wang D, Xie N, Yi S, Liu C, Jiang H, Ma Z, Feng J, Yan H, Zhang X. Bioassay- guided isolation of potent aphicidal Erythrina alkaloids against Aphis gossypii from the seed of Erythrina crista-galli L. Pest Manag Sci. 2018 Jan;74(1):210-218. doi: 10.1002/ps.4698. Epub 2017 Sep 27. PMID: 28799721. 10: Zarev Y, Foubert K, Cos P, Maes L, Elgorashi E, Apers S, Ionkova I, Pieters L. HPLC-DAD-SPE-NMR isolation of tetracyclic spiro-alkaloids with antiplasmodial activity from the seeds of Erythrina latissima. Nat Prod Res. 2020 Apr;34(7):1037-1040. doi: 10.1080/14786419.2018.1539976. Epub 2019 Jan 3. PMID: 30602319. 11: Ding WQ, Shi GR, Yu SS. [Chemical compositions from roots of Erythrina corallodendron]. Zhongguo Zhong Yao Za Zhi. 2019 Jul;44(14):3064-3069. Chinese. doi: 10.19540/j.cnki.cjcmm.20190520.204. PMID: 31602854. 12: Patil VS, Meena H, Harish DR. Erythrina variegata L. bark: an untapped bioactive source harbouring therapeutic properties for the treatment of Alzheimer's disease. In Silico Pharmacol. 2021 Aug 26;9(1):51. doi: 10.1007/s40203-021-00110-0. PMID: 34532215; PMCID: PMC8390608. 13: Wanjala CC, Majinda RR. Two novel glucodienoid alkaloids from Erythrina latissima seeds. J Nat Prod. 2000 Jun;63(6):871-3. doi: 10.1021/np990540d. PMID: 10869225. 14: AbouZeid EM, Hussein RA, Salama AA, Youssef FS, El-Ahmady SH, Ammar NM, Afifi AH. Metabolomic study of the estrogenic and anti-osteoporotic potential of Erythrina bidwillii leaf. Biomed Chromatogr. 2024 Mar;38(3):e5810. doi: 10.1002/bmc.5810. Epub 2023 Dec 25. PMID: 38146195. 15: Tan QW, Ni JC, Fang PH, Chen QJ. A New Erythrinan Alkaloid Glycoside from the Seeds of Erythrina crista-galli. Molecules. 2017 Sep 16;22(9):1558. doi: 10.3390/molecules22091558. PMID: 28926959; PMCID: PMC6151707. 16: Pereira ASP, den Haan H, Peña-García J, Moreno MM, Pérez-Sánchez H, Apostolides Z. Exploring African Medicinal Plants for Potential Anti-Diabetic Compounds with the DIA-DB Inverse Virtual Screening Web Server. Molecules. 2019 May 24;24(10):2002. doi: 10.3390/molecules24102002. PMID: 31137754; PMCID: PMC6571761. 17: Mohammed MM, Ibrahim NA, Awad NE, Matloub AA, Mohamed-Ali AG, Barakat EE, Mohamed AE, Colla PL. Anti-HIV-1 and cytotoxicity of the alkaloids of Erythrina abyssinica Lam. growing in Sudan. Nat Prod Res. 2012;26(17):1565-75. doi: 10.1080/14786419.2011.573791. Epub 2011 Sep 21. Erratum in: Nat Prod Res. 2013;27(3):295. PMID: 21936641. 18: Cui L, Thuong PT, Fomum ZT, Oh WK. A new Erythrinan alkaloid from the seed of Erythrina addisoniae. Arch Pharm Res. 2009 Mar;32(3):325-8. doi: 10.1007/s12272-009-1302-2. Epub 2009 Apr 23. PMID: 19387573.

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