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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

Molecular phylogeography of Carapichea ipecacuanha, an amphitropical shrub that occurs in the understory of both semideciduous and evergreen forests.

de Oliveira LO1, Rossi AA, Martins ER, Batista FR, Silva RS.
Molecular ecology.Mol Ecol.2010 Apr;19(7):1410-22. doi: 10.1111/j.1365-294X.2010.04591.x. Epub 2010 Mar 8.
The medicinal shrub Carapichea ipecacuanha (ipecac) is an amphitropic species with three disjunct areas of distribution. In the Brazilian Atlantic and Amazonian ranges, the species was associated mostly with the understory of seasonal semideciduous forests, whereas in the Central American-Colombian
PMID 20298468

Three new O-methyltransferases are sufficient for all O-methylation reactions of ipecac alkaloid biosynthesis in root culture of Psychotria ipecacuanha.

Nomura T1, Kutchan TM.
The Journal of biological chemistry.J Biol Chem.2010 Mar 5;285(10):7722-38. doi: 10.1074/jbc.M109.086157. Epub 2010 Jan 8.
The medicinal plant Psychotria ipecacuanha produces ipecac alkaloids, a series of monoterpenoid-isoquinoline alkaloids such as emetine and cephaeline, whose biosynthesis derives from condensation of dopamine and secologanin. Here, we identified three cDNAs, IpeOMT1-IpeOMT3, encoding ipecac alkaloid
PMID 20061395

Studies for the emetic mechanisms of ipecac syrup (TJN-119) and its active components in ferrets: involvement of 5-hydroxytryptamine receptors.

Hasegawa M1, Sasaki T, Sadakane K, Tabuchi M, Takeda Y, Kimura M, Fujii Y.
Japanese journal of pharmacology.Jpn J Pharmacol.2002 Jun;89(2):113-9.
Ipecac syrup, prepared from a galentical ipecac, contains the nauseant alkaloids cephaeline and emetine. The involvement of receptors and serotonin- and dopamine-metabolizing enzymes in the emesis induced by ipecac syrup and these components was investigated. 1) In ferrets, the selective 5-HT3-recep
PMID 12120752

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Cephaeline - Wikipedia, the free

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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
ChEMBL	ChEMBL255708
ChemSpider	390702
Jmol interactive 3D	Image
PubChem	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).
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	Infobox references

　　[★]

英: desmethylemetine
関: セファエリン

[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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案内

案内

desmethylemetine