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;
ChEMBL	ChEMBL255708 ;
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	466.622 g·mol−1
Appearance	White silky crystals
Solubility in ethanol	Soluble
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

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. Archived from the original on 2010-07-06. Retrieved 31 December 2009.

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[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. Archived from the original on 2010-07-06. Retrieved 31 December 2009.