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.

Cephaeline
Names
IUPAC name
7′,10,11-Trimethoxyemetan-6′-ol
Systematic IUPAC name
(1R)-1-{[(2S,3R,11bS)-3-Ethyl-9,10-dimethoxy-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-yl]methyl}-7-methoxy-1,2,3,4-tetrahydroisoquinolin-6-ol
Other names
Cepheline; Desmethylemetine; Dihydropsychotrine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.006.902 Edit this at Wikidata
KEGG
UNII
  • 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 checkY
    Key: DTGZHCFJNDAHEN-OZEXIGSWSA-N checkY
  • CC[C@H]1CN2CCc3cc(c(cc3[C@@H]2C[C@@H]1C[C@@H]4c5cc(c(cc5CCN4)O)OC)OC)OC
Properties
C28H38N2O4
Molar mass 466.622 g·mol−1
Appearance White silky crystals
Solubility in ethanol Soluble[vague]
Hazards
Occupational safety and health (OHS/OSH):
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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Poison treatment

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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

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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. ^ American Academy Of Pediatrics Committee On Injury, Violence (November 2003). "Policy statement: Poison treatment in the home". Pediatrics. 112 (5): 1182–1185. doi:10.1542/peds.112.5.1182. PMID 14595067.