Cephaeline

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Not to be confused with cephalin.
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).
checkY verify (what is checkY☒N ?)

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

  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.
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