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Coclaurine

From Wikipedia, the free encyclopedia
Coclaurine
Names
Preferred IUPAC name
(1S)-1-[(4-Hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol
Identifiers
3D model (JSmol)
ChemSpider
KEGG
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 mass285.343 g·mol−1
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

Coclaurine is anicotinic acetylcholine receptorantagonist[1] which has been isolated from a variety of plant sources includingNelumbo nucifera,Sarcopetalum harveyanum,[2]Ocotea duckei,[3] and others. It belongs to the class oftetrahydroisoquinolinealkaloids.Dimerization of coclaurine leads to the biscoclaurine alkaloids such ascepharanthine.

References

[edit]
  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.
nAChRsTooltip Nicotinic acetylcholine receptors
Agonists
(andPAMsTooltip positive allosteric modulators)
Antagonists
(andNAMsTooltip negative allosteric modulators)
Precursors
(andprodrugs)


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