Coclaurine

Last updated
Coclaurine
Coclaurine.svg
Names
Preferred IUPAC name
(1S)-1-[(4-Hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol
Identifiers
3D model (JSmol)
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C17H19NO3/c1-21-17-9-12-6-7-18-15(14(12)10-16(17)20)8-11-2-4-13(19)5-3-11/h2-5,9-10,15,18-20H,6-8H2,1H3/t15-/m0/s1
    Key: LVVKXRQZSRUVPY-HNNXBMFYSA-N
  • InChI=1/C17H19NO3/c1-21-17-9-12-6-7-18-15(14(12)10-16(17)20)8-11-2-4-13(19)5-3-11/h2-5,9-10,15,18-20H,6-8H2,1H3/t15-/m0/s1
    Key: LVVKXRQZSRUVPY-HNNXBMFYBJ
  • COC1=C(C=C2[C@@H](NCCC2=C1)CC3=CC=C(C=C3)O)O
Properties
C17H19NO3
Molar mass 285.343 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Coclaurine is a nicotinic acetylcholine receptor antagonist [1] which has been isolated from a variety of plant sources including Nelumbo nucifera , Sarcopetalum harveyanum , [2] Ocotea duckei , [3] and others. It belongs to the class of tetrahydroisoquinoline alkaloids. Dimerization of coclaurine leads to the biscoclaurine alkaloids such as cepharanthine.

References

  1. ↑ Cock, Ian Edwin; Cheesman, Matthew J. (May 2016). "Oceania: Antidepressant Medicinal Plants" (PDF). ResearchGate. p. 503.
  2. ↑ Sowemimo BO, Beal JL, Doskotch RW, Svoboda GH (1972). "The isolation of stepharine and coclaurine from Sarcopetalum harveyanum". Lloydia . 35 (1): 90–91. PMID   5037484.
  3. ↑ I.G da Silva; J.M Barbosa-Filho; M.S da Silva; C.D.G de Lacerda; E.V.L da-Cunha (2002). "Coclaurine from Ocotea duckei". Biochemical Systematics and Ecology. 30 (9): 881–883. Bibcode:2002BioSE..30..881D. doi:10.1016/s0305-1978(02)00024-8.


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