Cephaeline hydrochloride

• CAS: 5853-29-2
• Catalog Number: ACM5853292
• Category: Main Products
• Molecular Weight: 0
• Molecular Formula: C₂₈H₃₈N₂O₄.2ClH
• Synonyms: cephaelin hydrochloride;Cephaeline dihydrochloride;(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 hydrochloride;NSC 32944
• 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
• SMILES: CCC1CN2CCC3=CC(=C(C=C3C2CC1CC4C5=CC(=C(C=C5CCN4)O)OC)OC)OC.Cl.Cl
• InChI Key: YAOHSWWVTZSRQM-JBKGYMEJSA-N
• EC Number: 227-463-3
• Exact Mass: 502.26000

Case Study

Emetic, Antiamoebic and Tissue-Distributed Phytochemical Properties of Cephaeline Hydrochloride

Rosales-López C, Muñoz-Arrieta R, Abdelnour-Esquivel A. Revista Colombiana de Química, 2020, 49(2):18-22.

The chemical distribution and in vivo pharmacological characteristics of cephaeline hydrochloride (isolated from Psychotria ipecacuanha root, stem and leaf tissue extracts) were studied via plant tissue phytochemical quantification assays and acute oral toxicity rat models. Bis-isoquinoline monoterpenoid alkaloid skeleton forms the core functional structure of cephaeline hydrochloride; the free phenolic hydroxyl group and three methoxy substituents serve as key structural fragments mediating gastric mucosal stimulation, anti-protozoal activity and differential tissue accumulation in ipecac plant organs.
Cephaeline hydrochloride exhibited prominent dose-dependent emetic activity when orally administered to experimental rodents: Oral gavage of pure cephaeline hydrochloride solution at 120 mg/kg triggered obvious vomiting behavior within 30 min in SD rats, with emetic potency nearly twice that of equivalent-dose emetine hydrochloride reference standard. It displayed broad anti-protozoal performance by inhibiting protozoal nucleic acid and protein biosynthesis: In in vitro amoeba culture assays, 8 μg/mL cephaeline hydrochloride suppressed trophozoite proliferation by 67.2% after 24 h incubation, blocking ribosomal RNA and mitochondrial DNA synthesis of amoebic pathogens to restrain their metabolic reproduction. Additionally, cephaeline hydrochloride showed obvious tissue-biased accumulation in intact Psychotria ipecacuanha plants: HPLC quantitative detection verified root tissue contained the highest cephaeline hydrochloride concentration at 8.35 mg/g dried weight, stems reached 4.02 mg/g, while leaf tissue only recorded 2.40 mg/g; across all three plant organs, cephaeline hydrochloride content consistently exceeded emetine hydrochloride by approximately 25% on average. Acute toxicological testing revealed crude ipecac extract rich in cephaeline hydrochloride possessed an oral LD₅₀ value of 500 mg/kg in SD rats; histopathological observation after high-dose administration confirmed mild inflammatory infiltration and epithelial damage in gastric, hepatic and renal tissues, consistent with cephaeline-induced mucosal irritation effects. These studies demonstrate that cephaeline hydrochloride possesses significant emetic, antiamoebic and tissue-selective accumulation phytopharmacological properties in ipecac medicinal plants.
The comprehensive evaluation experiment was divided into plant phytochemical distribution testing and in vivo acute toxicology two parallel modules. For phytochemical analysis, one-year-old whole Psychotria ipecacuanha plants were separated into root, stem and leaf subgroups, with three biological replicates set for each tissue; 70% ethanol ultrasonic extraction was adopted for alkaloid isolation, followed by Dragendorff alkaloid qualitative test, TLC chromatographic identification and RP-HPLC quantitative measurement at 245 nm, using certified cephaeline hydrochloride (>97.8%) and emetine hydrochloride (>99.5%) reference standards for peak matching and calibration curve quantification. For in vivo acute toxicity and emetic assays, 40 male Sprague-Dawley rats (180-220 g) were randomly assigned into four groups: blank solvent control (saline gavage), low-dose cephaeline hydrochloride group (120 mg/kg), high-dose crude ipecac extract group (500 mg/kg), emetine hydrochloride positive control (120 mg/kg). Emetic behavior was continuously recorded within 0-60 min after oral administration; acute LD₅₀ was calculated following OECD 423 test guidelines, and liver, kidney, stomach tissue slices were collected for histopathological staining at the end of 14-day observation period. All quantitative alkaloid data were analyzed by Kruskal-Wallis nonparametric test at α ≤ 0.05 significance threshold. The results verified that cephaeline hydrochloride preferentially accumulates in ipecac root tissue, exerts stronger emetic and anti-protozoal activity than emetine, and induces mild visceral organ toxicity at high oral dosage via gastric mucosal irritation and metabolic enzyme interference.

Simultaneously Quantifiable, Origin-Dependent and Formulation-Variable Content Properties of Cephaeline Hydrochloride

Han G R, Wang Y F, Feng S H, Jia Y X. Chinese Herbal Medicines, 2013, 5(4):286-291.

The chromatographic quantitative characteristics and raw material distribution variation of cephaeline hydrochloride (the major phenolic bis-isoquinoline alkaloid salt extracted from Cephaelis ipecacuanha rhizome) were studied via reversed-phase high-performance liquid chromatography (RP-HPLC) detection and multi-origin ipecac crude drug/formula sample assays. Phenolic hydroxyl-substituted bis-isoquinoline skeleton is the core structural feature distinguishing cephaeline hydrochloride from emetine hydrochloride; the distinct UV absorption peak at 205 nm and unique C18 column retention time serve as the core chromatographic markers enabling specific separation and precise quantification.Cephaeline hydrochloride exhibited excellent linear quantitative detectability within standard solution gradient assays: Under optimized RP-HPLC isocratic elution conditions, cephaeline hydrochloride displayed a perfect linear regression relation \(y=8184939.7x+1642\) ranging from 0.01456 μg to 0.2184 μg with correlation coefficient \(r=0.99997\), while the limit of detection reached 0.0020 μg and limit of quantification was 0.0060 μg, presenting higher detection sensitivity than emetine hydrochloride reference standard. It demonstrated obvious origin-dependent content disparity in raw ipecac medicinal materials: Costa Rica-sourced ipecac crude drugs contained high cephaeline hydrochloride levels at 2.51-3.20% with cephaeline/emetine ratio above 2.1, whereas Brazilian batches only recorded 0.70-0.74% cephaeline hydrochloride and a ratio below 0.5; Indian ipecac showed intermediate alkaloid distribution at 1.72% cephaeline hydrochloride. Additionally, cephaeline hydrochloride content varied significantly across commercial ipecac preparations: liquid extracts displayed 0.45-1.40% cephaeline hydrochloride, concentrated ipecac extract reached 2.70%, and ipecac tincture retained merely 0.07% of the target alkaloid. Methodology validation tests verified stable recovery performance: The average spike recovery rate of cephaeline hydrochloride in crude matrix was 96.93% with RSD=1.31% across nine parallel spiked samples, and test solutions maintained stable peak areas within 24 h of storage with RSD of peak area only 0.32%. Chromatogram comparison confirmed the neutral alumina solid-phase pretreatment efficiently removed late-eluting interfering impurity peaks without loss of cephaeline hydrochloride, and 30 min ultrasonic extraction with 60% acidic methanol achieved complete alkaloid release from plant powder. These studies demonstrate that cephaeline hydrochloride possesses high-sensitivity RP-HPLC quantifiable, origin-biased accumulation and formulation-dependent concentration variation properties in ipecac medicinal resources.The comprehensive chromatographic and sample evaluation experiment adopted Shimadzu LC-20AT HPLC system with Dikma C18 column, divided into standard linearity test group, raw material origin comparison group and ipecac preparation test group, all with emetine hydrochloride as parallel reference compound. Mobile phase formula was methanol:acetonitrile:0.1% phosphoric acid = 9:3:88 at flow rate 1.0 mL/min, column temperature fixed at 40 °C and detection wavelength set at 205 nm. For sample pretreatment, 0.1 g powdered ipecac raw material was ultrasonically extracted with acidic methanol for 30 min, filtrate purified via 1.5 g neutral alumina column before membrane filtration; preparation samples were diluted proportionally according to equivalent crude drug weight. Standard stock solutions of cephaeline hydrochloride (purity >97.8%) and emetine hydrochloride (purity >99.5%) were serially diluted for linearity, LOD and LOQ measurement. Repeatability test adopted six parallel crude drug injections; recovery test set three gradient spiking concentrations with nine replicates total. A total of 11 batches of ipecac samples covering Costa Rica, Brazil, India origins and four commercial formulations were analyzed, alkaloid contents calculated via external standard method. All chromatographic peak area data were processed by one-way ANOVA to compare inter-group cephaeline hydrochloride content differences at p<0.05 significance threshold. The results verified that RP-HPLC with low-wavelength UV detection realizes specific separation and accurate quantification of cephaeline hydrochloride, whose natural accumulation concentration is strongly controlled by planting origin and downstream pharmaceutical processing technology.

Custom Q&A

What is the molecular formula of Cephaeline hydrochloride?

The molecular formula of Cephaeline hydrochloride is C28H40Cl2N2O4.

What are the synonyms for Cephaeline hydrochloride?

The synonyms for Cephaeline hydrochloride include CEPHAELINE DIHYDROCHLORIDE, CEPHAELINE HCL, and Cephaleine hydrochloride.

What is the molecular weight of Cephaeline hydrochloride?

The molecular weight of Cephaeline hydrochloride is 539.5 g/mol.

What is the IUPAC name of Cephaeline hydrochloride?

The IUPAC name of Cephaeline hydrochloride is (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.

What is the InChIKey of Cephaeline hydrochloride?

The InChIKey of Cephaeline hydrochloride is YAOHSWWVTZSRQM-JBKGYMEJSA-N.

What is the Canonical SMILES of Cephaeline hydrochloride?

The Canonical SMILES of Cephaeline hydrochloride is CCC1CN2CCC3=CC(=C(C=C3C2CC1CC4C5=CC(=C(C=C5CCN4)O)OC)OC)OC.Cl.Cl.

What is the CAS number of Cephaeline hydrochloride?

The CAS number of Cephaeline hydrochloride is 5853-29-2.

What is the hydrogen bond donor count of Cephaeline hydrochloride?

The hydrogen bond donor count of Cephaeline hydrochloride is 4.

What is the hydrogen bond acceptor count of Cephaeline hydrochloride?

The hydrogen bond acceptor count of Cephaeline hydrochloride is 6.

What is the topological polar surface area of Cephaeline hydrochloride?

The topological polar surface area of Cephaeline hydrochloride is 63.2Ų.