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Coclaurine
Names
IUPAC name
(1S )-1-[(4-hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol
Identifiers
ChemSpider
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
C 17 H 19 N O 3
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).
Chemical compound
Coclaurine is a nicotinic acetylcholine receptor antagonist [citation needed ] which has been isolated from a variety of plant sources including Nelumbo nucifera , Sarcopetalum harveyanum ,[1] Ocotea duckei ,[2] and others. It belongs to the class of tetrahydroisoquinoline alkaloids . Dimerization of coclaurine leads to the biscoclaurine alkaloids such as cepharanthine .
References
^ 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 . {{cite journal }}
: CS1 maint: multiple names: authors list (link )
^ 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. doi :10.1016/s0305-1978(02)00024-8 . {{cite journal }}
: CS1 maint: multiple names: authors list (link )
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