cephaeline

Cephaeline
Names
	IUPAC name (1R)-1-[[(2S,3R,11bS)-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-pyrido[2,1-a]isoquinolin-2-yl]methyl]-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol
	Other names Cepheline; Desmethylemetine; Dihydropsychotrine
Identifiers
CAS Number	483-17-0 ;
3D model (JSmol)	Interactive image;
ChemSpider	390702 ;
ECHA InfoCard	100.006.902
PubChem CID	442195;
UNII	QA971541A1 ;
	InChI 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 Key: DTGZHCFJNDAHEN-OZEXIGSWSA-N ;
	SMILES CC[C@H]1CN2CCc3cc(c(cc3[C@@H]2C[C@@H]1C[C@@H]4c5cc(c(cc5CCN4)O)OC)OC)OC ;
Properties
Chemical formula	C28H38N2O4
Molar mass	466.62 g·mol−1
Appearance	White silky crystals
Solubility in ethanol	Soluble[vague]
Hazards
Main hazards	Emetic / poisonous
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
	verify (what is ?)
	Infobox references

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2018/01/15 10:46:27」(JST)

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Cephaeline is an alkaloid that is found in Cephaelis ipecacuanha and other plant species including Psychotria acuminata.^[1] Cephaeline induces vomiting by stimulating the stomach lining and is found in commercial products such as syrup of ipecac.^[2] Chemically, it is closely related to emetine.

Poison treatment

Cephaeline in the form of syrup of ipecac was once commonly recommended as an emergency treatment for accidental poisoning, but its use has been phased out due to its ineffectiveness.^[3]

References

^ Lara, Alfonso; Valverde, Roberto; Gomez, Luis; Hidalgo, Nancy (July 1, 2003). "Micropropagacion de la planta medicinal psychotria acuminata". Agronomía Costarricense. Retrieved 26 December 2009.
^ "Pharma Japan: Approval of 4 drugs including Seroquel recommended: CPAC panel". Chemical Business Newsbase. November 14, 2000. Retrieved 26 December 2009.
^ "Policy statement: Poison treatment in the home". Pediatrics. 112 (5): 1182–1185. November 2003. doi:10.1542/peds.112.5.1182. PMID 14595067. Retrieved 31 December 2009.

English Journal

hERG Channel Blocking Ipecac Alkaloids Identified by Combined In Silico - In Vitro Screening.

Kratz JM1, Mair CE1, Oettl SK2, Saxena P3, Scheel O4, Schuster D5, Hering S3, Rollinger JM1.
Planta medica.Planta Med.2016 May 4. [Epub ahead of print]
Human ether-a-go-go-related gene channel blocking is associated with QT interval prolongation and increased risk of potentially fatal arrhythmias. As natural products keep increasing in popularity, there is an urgent need for studies assessing human ether-a-go-go-related gene channel-related cardiot
PMID 27145237

Angustinine--a new benzopyridoquinolizine alkaloid from Alangium lamarckii.

Chakraborty M1, Mukhopadhyay S.
Natural product communications.Nat Prod Commun.2012 Sep;7(9):1169-70.
A new benzopyridoquinolizine alkaloid, designated as angustinine (1), was isolated from the root bark of Alangium lamarckii Thwaites, along with the known ipecac alkaloid, emetine. Investigation of the stem bark of the same plant resulted in the isolation of another known ipecac alkaloid, cephaeline
PMID 23074898

[Rapid detection of alkaloids in Ipecac by direct analysis in real time tandem mass spectrometry (DART-MS/MS)].

Sun L1, Hu X, Liu L, Jin H, Lin R.
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica.Zhongguo Zhong Yao Za Zhi.2012 May;37(10):1426-30.
OBJECTIVE: To detect alkaloids in Ipecac by direct analysis in real time tandem mass spectrometry (DART-MS) without pre-treatment and chromatographic separation.METHOD: Under the optimum conditions, DART-MS characteristic spectra were collected for tablet of Ipecac powder, Ipecac stems and leaves by
PMID 22860455

Japanese Journal

Molecular Cloning of an O-Methyltransferase from Adventitious Roots of Carapichea ipecacuanha

Cheong Bo Eng,Takemura Tomoya,Yoshimatsu Kayo [他],SATO Fumihiko
Bioscience, biotechnology, and biochemistry 75(1), 107-113, 2011-01-23
… The encoded protein (CiOMT1) showed 98% sequence identity to IpeOMT2, which catalyzes the 7′-O-methylation of 7′-O-demethylcephaeline to form cephaeline at the penultimate step of emetine biosynthesis (Nomura and Kutchan, J. …
NAID 10027896875

Studies for the Emetic Mechanisms ofIpecac Syrup (TJN-119) and Its Active Components in Ferrets: Involvement of 5-Hydroxytryptamine Receptors

Hasegawa Masayuki,Sasaki Toshinobu,Sadakane Koichi [他],TABUCHI Masahiro,TAKEDA Yasunori,KIMURA Masayuki,FUJII Yuichi
The Japanese journal of pharmacology 89(2), 113-119, 2002-06-01
… Ipecac syrup, prepared from a galentical ipecac, contains the nauseant alkaloids cephaeline and emetine. …
NAID 130000078493

High-performance liquid chromatographic assay with fluorescence detection for the determination of cephaeline and emetine in human plasma and urine

ASANO Takayuki,SADAKANE Chiharu,ISHIHARA Kazuhisa,YANAGISAWA Toshihiko,KIMURA Masayuki,KAMEI Hideo
Journal of chromatography. B, Biomedical sciences and applications 757(2), 197-206, 2001-06-15
NAID 10012244103

Related Pictures

[1] Lara, Alfonso; Valverde, Roberto; Gomez, Luis; Hidalgo, Nancy (July 1, 2003). "Micropropagacion de la planta medicinal psychotria acuminata". Agronomía Costarricense. Retrieved 26 December 2009.

[2] "Pharma Japan: Approval of 4 drugs including Seroquel recommended: CPAC panel". Chemical Business Newsbase. November 14, 2000. Retrieved 26 December 2009.

[3] "Policy statement: Poison treatment in the home". Pediatrics. 112 (5): 1182–1185. November 2003. doi:10.1542/peds.112.5.1182. PMID 14595067. Retrieved 31 December 2009.

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