Coclaurine

Coclaurine

Names
IUPAC name (1S)-1-[(4-hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol
Identifiers
CAS Number	486-39-5
3D model (Jmol)	Interactive image
ChemSpider	141028
PubChem	160487
InChI 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
SMILES COC1=C(C=C2[C@@H](NCCC2=C1)CC3=CC=C(C=C3)O)O
Properties
Chemical formula	C17H19NO3
Molar mass	285.34 g·mol^−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Coclaurine is a nicotinic acetylcholine receptor antagonist 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

1. 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.
2. 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.