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MedKoo Cat#: 565579 | Name: Cephaeline

Description:

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

Cephaeline is an alkaloid that is found in Cephaelis ipecacuanha and other plant species including Psychotria acuminata. Cephaeline induces vomiting by stimulating the stomach lining and is found in commercial products such as syrup of ipecac. Chemically, it is closely related to emetine.

Chemical Structure

Cephaeline
CAS#5483-17-0

Theoretical Analysis

MedKoo Cat#: 565579

Name: Cephaeline

CAS#: 5483-17-0

Chemical Formula: C28H38N2O4

Exact Mass: 466.2832

Molecular Weight: 466.62

Elemental Analysis: C, 72.07; H, 8.21; N, 6.00; O, 13.71

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 #
483-17-0
Synonym
Cephaeline
IUPAC/Chemical Name
(1R)-1-[[(2S,3R,11bS)-3-Ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizin-2-yl]methyl]-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol
InChi Key
DTGZHCFJNDAHEN-OZEXIGSWSA-N
InChi Code
InChI=1S/C28H38N2O4/c1-5-17-16-30-9-7-19-13-27(33-3)28(34-4)15-22(19)24(30)11-20(17)10-23-21-14-26(32-2)25(31)12-18(21)6-8-29-23/h12-15,17,20,23-24,29,31H,5-11,16H2,1-4H3/t17-,20-,23+,24-/m0/s1
SMILES Code
OC1=CC2=C([C@@H](C[C@@H]3[C@@H](CC)CN4CCC5=CC(OC)=C(OC)C=C5[C@]4([H])C3)NCC2)C=C1OC
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
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 466.62 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: Yosifov DY, Idler I, Bhattacharya N, Reichenzeller M, Close V, Ezerina D, Scheffold A, Jebaraj BMC, Kugler S, Bloehdorn J, Bahlo J, Robrecht S, Eichhorst B, Fischer K, Weigel A, Busch H, Lichter P, Döhner H, Dick TP, Stilgenbauer S, Mertens D. Oxidative stress as candidate therapeutic target to overcome microenvironmental protection of CLL. Leukemia. 2019 Jul 12. doi: 10.1038/s41375-019-0513-x. [Epub ahead of print] PubMed PMID: 31300746. 2: Zhang J, Harvey SE, Cheng C. A high-throughput screen identifies small molecule modulators of alternative splicing by targeting RNA G-quadruplexes. Nucleic Acids Res. 2019 Apr 23;47(7):3667-3679. doi: 10.1093/nar/gkz036. PubMed PMID: 30698802; PubMed Central PMCID: PMC6468248. 3: Yang S, Xu M, Lee EM, Gorshkov K, Shiryaev SA, He S, Sun W, Cheng YS, Hu X, Tharappel AM, Lu B, Pinto A, Farhy C, Huang CT, Zhang Z, Zhu W, Wu Y, Zhou Y, Song G, Zhu H, Shamim K, Martínez-Romero C, García-Sastre A, Preston RA, Jayaweera DT, Huang R, Huang W, Xia M, Simeonov A, Ming G, Qiu X, Terskikh AV, Tang H, Song H, Zheng W. Emetine inhibits Zika and Ebola virus infections through two molecular mechanisms: inhibiting viral replication and decreasing viral entry. Cell Discov. 2018 Jun 5;4:31. doi: 10.1038/s41421-018-0034-1. eCollection 2018. PubMed PMID: 29872540; PubMed Central PMCID: PMC5986771. 4: Xun Z, Liu D, Huang R, He S, Hu D, Guo X, Xian Y. Simultaneous determination of eight alkaloids and oleandrin in herbal cosmetics by dispersive solid-phase extraction coupled with ultra high performance liquid chromatography and tandem mass spectrometry. J Sep Sci. 2017 May;40(9):1966-1973. doi: 10.1002/jssc.201601427. Epub 2017 Apr 19. PubMed PMID: 28317265. 5: Kratz JM, Mair CE, Oettl SK, Saxena P, Scheel O, Schuster D, Hering S, Rollinger JM. hERG Channel Blocking Ipecac Alkaloids Identified by Combined In Silico - In Vitro Screening. Planta Med. 2016 Jul;82(11-12):1009-15. doi: 10.1055/s-0042-105572. Epub 2016 May 4. PubMed PMID: 27145237. 6: Chakraborty M, Mukhopadhyay S. Angustinine--a new benzopyridoquinolizine alkaloid from Alangium lamarckii. Nat Prod Commun. 2012 Sep;7(9):1169-70. PubMed PMID: 23074898. 7: Sun L, Hu X, Liu L, Jin H, Lin R. [Rapid detection of alkaloids in Ipecac by direct analysis in real time tandem mass spectrometry (DART-MS/MS)]. Zhongguo Zhong Yao Za Zhi. 2012 May;37(10):1426-30. Chinese. PubMed PMID: 22860455. 8: Zhang W, Bah J, Wohlfarth A, Franzén J. A stereodivergent strategy for the preparation of corynantheine and ipecac alkaloids, their epimers, and analogues: efficient total synthesis of (-)-dihydrocorynantheol, (-)-corynantheol, (-)-protoemetinol, (-)-corynantheal, (-)-protoemetine, and related natural and nonnatural compounds. Chemistry. 2011 Dec 2;17(49):13814-24. doi: 10.1002/chem.201102012. Epub 2011 Nov 3. PubMed PMID: 22052788. 9: Freitas CS, Baggio CH, Mayer B, dos Santos AC, Twardowschy A, Santos CA, Marques MC. Inhibition of gastric H+, K(+)-ATPase activity by compounds from medicinal plants. Nat Prod Commun. 2011 Sep;6(9):1253-4. PubMed PMID: 21941891. 10: Brown SJ, Bachovchin DA, Cravatt BF, Fernandez-Vega V, Spicer T, Mercer BA, Hodder P, Rosen HR. Probe Report for RBBP9 Inhibitors - Probe 1. 2009 Mar 13 [updated 2010 Sep 2]. Probe Reports from the NIH Molecular Libraries Program [Internet]. Bethesda (MD): National Center for Biotechnology Information (US); 2010-. Available from http://www.ncbi.nlm.nih.gov/books/NBK47337/ PubMed PMID: 21433353. 11: Cheong BE, Takemura T, Yoshimatsu K, Sato F. Molecular cloning of an O-methyltransferase from adventitious roots of Carapichea ipecacuanha. Biosci Biotechnol Biochem. 2011;75(1):107-13. Epub 2011 Jan 7. PubMed PMID: 21228475. 12: Nomura T, Kutchan TM. Is a metabolic enzyme complex involved in the efficient and accurate control of Ipecac alkaloid biosynthesis in Psychotria ipecacuanha? Plant Signal Behav. 2010 Jul;5(7):875-7. doi: 10.1074/jbc.M109.086157. Epub 2010 Jul 1. PubMed PMID: 20495341; PubMed Central PMCID: PMC3115036. 13: de Oliveira LO, Rossi AA, Martins ER, Batista FR, Silva RS. Molecular phylogeography of Carapichea ipecacuanha, an amphitropical shrub that occurs in the understory of both semideciduous and evergreen forests. Mol Ecol. 2010 Apr;19(7):1410-22. doi: 10.1111/j.1365-294X.2010.04591.x. Epub 2010 Mar 8. PubMed PMID: 20298468. 14: Nomura T, Kutchan TM. Three new O-methyltransferases are sufficient for all O-methylation reactions of ipecac alkaloid biosynthesis in root culture of Psychotria ipecacuanha. J Biol Chem. 2010 Mar 5;285(10):7722-38. doi: 10.1074/jbc.M109.086157. Epub 2010 Jan 8. PubMed PMID: 20061395; PubMed Central PMCID: PMC2844217. 15: Lee MR. Ipecacuanha: the South American vomiting root. J R Coll Physicians Edinb. 2008 Dec;38(4):355-60. PubMed PMID: 19227966. 16: Nomura T, Quesada AL, Kutchan TM. The new beta-D-glucosidase in terpenoid-isoquinoline alkaloid biosynthesis in Psychotria ipecacuanha. J Biol Chem. 2008 Dec 12;283(50):34650-9. doi: 10.1074/jbc.M806953200. Epub 2008 Oct 16. PubMed PMID: 18927081; PubMed Central PMCID: PMC3259899. 17: Yoshimatsu K, Shimomura K, Yamazaki M, Saito K, Kiuchi F. Transformation of ipecac (Cephaelis ipecacuanha) with Agrobacterium rhizogenes. Planta Med. 2003 Nov;69(11):1018-23. PubMed PMID: 14735440. 18: Muhammad I, Dunbar DC, Khan SI, Tekwani BL, Bedir E, Takamatsu S, Ferreira D, Walker LA. Antiparasitic alkaloids from Psychotria klugii. J Nat Prod. 2003 Jul;66(7):962-7. PubMed PMID: 12880315. 19: Yamashita M, Yamashita M, Azuma J. Urinary excretion of ipecac alkaloids in human volunteers. Vet Hum Toxicol. 2002 Oct;44(5):257-9. PubMed PMID: 12361104. 20: Hasegawa M, Sasaki T, Sadakane K, Tabuchi M, Takeda Y, Kimura M, Fujii Y. Studies for the emetic mechanisms of ipecac syrup (TJN-119) and its active components in ferrets: involvement of 5-hydroxytryptamine receptors. Jpn J Pharmacol. 2002 Jun;89(2):113-9. PubMed PMID: 12120752.

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