An alkaloid with diverse biological activities
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Cephaeline

Item No. 20916

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
(1R)-1-[[(2S,3R,11bS)-3-ethyl-1,3,4,6,7,11b-hexahydro-9,10-dimethoxy-2H-benzo[a]quinolizin-2-yl]methyl]-1,2,3,4-tetrahydro-7-methoxy-6-isoquinolinol
CAS Number
483-17-0
Synonyms
  • (-)-Cephaeline
Molecular Formula
C28H38N2O4
Formula Weight
466.6
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Acetonitrile: slightly solubleChloroform: slightly solubleEthanol: slightly solubleMethanol: slightly soluble
λmax
286 nm
SMILES
CC[C@H]1CN2CCC(C=C(C(OC)=C3)OC)=C3[C@]2([H])C[C@@H]1C[C@@]4(C5=CC(OC)=C(C=C5CCN4)O)[H]
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
InChi Key
DTGZHCFJNDAHEN-OZEXIGSWSA-N
Origin
Plant/Ipecacuanha
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
Certificates of Analysis & Batch Specific Data

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    500 µg

    $103

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    1 mg

    $194

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    Cayman Chemical
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    Product Description

    Cephaeline is an alkaloid originally isolated from C. ipecacuanha with diverse biological activities.1,2,3,4 It inhibits the cytochrome P450 (CYP) isoforms CYP2D6 and CYP3A4 in vitro (Kis = 54 and 355 μM, respectively).1 Cephaeline reduces Zika virus (ZIKV) NS1 protein expression in HEK293 cells (IC50 = 26.4 nM) and reduces viral titer in ZIKV-infected SNB-19 cells (IC50 = 3.11 nM).2 In vivo, cephaeline (2 mg/kg, i.p.) reduces serum viral load in ZIKV-infected Ifnar1-/- mice. It induces emesis in ferrets when administered at a dose of 0.5 mg/kg, an effect that is prevented by the serotonin (5-HT) receptor subtype 5-HT3 antagonist ondansetron.3 Cephaeline (1 mg/kg) also increases output of respiratory tract fluid in rabbits.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Asano, T., Kushida, H., Sadakane, C., et al. Metabolism of ipecac alkaloids cephaeline and emetine by human hepatic microsomal cytochrome P450s, and their inhibitory effects on P450 enzyme activities. Biol. Pharm. Bull. 24(6), 678-682 (2001).

    2. Yang, S., Xu, M., Lee, E.M., et al. Emetine inhibits Zika and Ebola virus infections through two molecular mechanisms: inhibiting viral replication and decreasing viral entry. Cell. Discov. 4, 31 (2018).

    3. Hasegawa, M., Sasaki, T., Sadakane, K., et al. Studies for the emetic mechanisms of ipecac syrup (TJN-119) and its active components in ferrets: Involvement of 5-hydroxytryptamine receptors. Jpn. J. Pharmacol. 89(2), 113-119 (2002).

    4. Boyd, E.M., and Knight, L.M. The expectorant action of cephaeline, emetine and 2-dehydroemetine. J. Pharm. Pharmacol. 16, 118-124 (1964).