Cephaeline dihydrochloride - ≥99% , CAS No.5853-29-2

CAS: 5853-29-2 Cat. No.: C651400 Molecular Weight: 539.53 EC Number: 227-463-3 PubChem CID: 23615629

GRADE & PURITY ≥99%

Synonyms

AKOS037514579 | EINECS 227-463-3 | (-)-Cephaeline (dihydrochloride) | Cephaelin Dihydrochloride | (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;chloride

Storage

Store at 2-8°C,Protected from light,Desiccated

Shipped In

Wet ice

Overview

Cephaeline dihydrochloride is a selective CYP2D6 inhibtor with an IC 50 of 121 μM.

In Vitro

CYP2D6 reveals the highest metabolic activity for the generation of 9-O-demethylEmetine, whereas this enzyme also shows a significant metabolic activity for the generation of Cephaeline. The IC 50 s of Cephaeline against CYP2C9, CYP2D6 and CYP3A4 is over 1000, 121 and 1000 μM, respectively. Further experiments are performed to determine inhibition constants (K i ) for Cephaeline on the CYP2D6 and CYP3A4 activities Graphic analysis of Dixon plots at various Cephaeline concentrations for each of the two CYP enzyme assays yield K i s of 54 and 355 μM for CYP2D6 and CYP3A4, respectively. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

Form:Solid

IC50& Target:IC50: 121 μM (CYP2D6), Ki: 54 μM (CYP2D6)

Specifications

Synonyms

AKOS037514579 | EINECS 227-463-3 | (-)-Cephaeline (dihydrochloride) | Cephaelin Dihydrochloride | (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;chloride

Specifications & Purity

≥99%

Biochemical and Physiological Mechanisms

Cephaeline dihydrochloride is a selective CYP2D6 inhibtor with an IC 50 of 121 μM.

Storage

Store at 2-8°C, Protected from light, Desiccated

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Purity

≥99%

Names and Identifiers

• Canonical Smiles: CCC1CN2CCC3=CC(=C(C=C3C2CC1CC4C5=CC(=C(C=C5CCN4)O)OC)OC)OC.Cl.Cl
• IUPAC 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;dihydrochloride
• InChIKey: YAOHSWWVTZSRQM-JBKGYMEJSA-N
• INCHI: 1S/C28H38N2O4.2ClH/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;2*1H/t17-,20-,23+,24-;;/m0../s1
• Isomeric SMILES: CC[C@H]1CN2CCC3=CC(=C(C=C3[C@@H]2C[C@@H]1C[C@@H]4C5=CC(=C(C=C5CCN4)O)OC)OC)OC.Cl.Cl
• Alternate CAS: 5853-29-2
• PubChem CID: 23615629
• Molecular Weight: 539.53

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Alkaloids and derivatives
    • Class Emetine alkaloids

• Kingdom: Organic compounds
• Superclass: Alkaloids and derivatives
• Class: Emetine alkaloids
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Emetine alkaloids
• Alternative Parents: Tetrahydroisoquinolines Quinolizidines Anisoles Aralkylamines Alkyl aryl ethers 1-hydroxy-2-unsubstituted benzenoids Piperidines Trialkylamines Dialkylamines Azacyclic compounds Hydrochlorides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Emetine alkaloid - Tetrahydroisoquinoline - Quinolizidine - Anisole - Phenol ether - Alkyl aryl ether - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Aralkylamine - Piperidine - Benzenoid - Tertiary aliphatic amine - Tertiary amine - Secondary aliphatic amine - Ether - Azacycle - Organoheterocyclic compound - Secondary amine - Organonitrogen compound - Amine - Hydrocarbon derivative - Organooxygen compound - Organic oxygen compound - Hydrochloride - Organic nitrogen compound - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as emetine alkaloids. These are alkaloids with a structure characterized by the presence of both an isoquinoline and a benzoquinolizidine nuclei.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(non-human)

pol Human immunodeficiency virus type 1 reverse transcriptase (18245 Activities)

Discover Target: pol

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO : 250 mg/mL (463.37 mM; Need ultrasonic) H2O : 125 mg/mL (231.68 mM; Need ultrasonic)
• Molecular Weight: 539.500 g/mol
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 538.237 Da
• Monoisotopic Mass: 538.237 Da
• Topological Polar Surface Area: 63.200 Ų
• Heavy Atom Count: 36
• Formal Charge: 0
• Complexity: 664.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 3

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