Coclaurine

Coclaurine
Names
	Preferred IUPAC name (1S)-1-[(4-Hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol
Identifiers
CAS Number	486-39-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	141028;
KEGG	C06161 ;
PubChem CID	160487;
UNII	CW1576313Y ;
CompTox Dashboard (EPA)	DTXSID60197561 ;
	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	285.343 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^[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

^ https://www.researchgate.net/profile/Matthew_Cheesman4/publication/303689274_Oceania_Antidepressant_Medicinal_Plants/links/5aa85083a6fdcc1b59c63bda/Oceania-Antidepressant-Medicinal-Plants.pdf ^{[bare URL PDF]}
^ 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.
^ 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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Names

Preferred IUPAC name (1S)-1-[(4-Hydroxyphenyl)methyl]-6-methoxy-1,2,3,4-tetrahydroisoquinolin-7-ol
Identifiers
CAS Number	486-39-5^Y
3D model (JSmol)	Interactive image
ChemSpider	141028
KEGG	C06161^Y
PubChem CID	160487
UNII	CW1576313Y^Y
CompTox Dashboard (EPA)	DTXSID60197561
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	285.343 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