Dauricine

Dauricine is a plant metabolite, chemically classified as a phenol, an aromatic ether, and an isoquinoline alkaloid.^[1] It has been isolated from the Asian vine Menispermum dauricum, Asian moonseed, and the North American vine Menispermum canadense, Canadian moonseed.^[2] Scientists Tetsuji Kametani and Keiichiro Fukumoto of Japan are credited with being the first to synthesize dauricine in 1964, using both the Arndt-Eistert reaction and Bischler-Napieralski reaction to do so.^[3] Dauricine has been studied in vitro for its potential to inhibit cancer cell growth^[4][5][6][7] and to block cardiac transmembrane Na⁺, K⁺, and Ca²⁺ ion currents.^[8]

Quick facts Names, Identifiers ...

Dauricine

Names
Preferred IUPAC name (11R,71R)-16,17,76,77-Tetramethoxy-12,72-dimethyl-11,12,13,14,71,72,73,74-octahydro-4-oxa-1,7(1)-diisoquinolina-3(1,3),5(1,4)-dibenzenaheptaphan-34-ol
Identifiers
CAS Number	524-17-4 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:4331
ChEMBL	ChEMBL442717
ChemSpider	66117
ECHA InfoCard	100.208.622
PubChem CID	73400
UNII	8QTO90G5W5 Y
CompTox Dashboard (EPA)	DTXSID90966808
InChI InChI=1/C38H44N2O6/c1-39-15-13-26-20-35(42-3)37(44-5)22-29(26)31(39)17-24-7-10-28(11-8-24)46-34-19-25(9-12-33(34)41)18-32-30-23-38(45-6)36(43-4)21-27(30)14-16-40(32)2/h7-12,19-23,31-32,41H,13-18H2,1-6H3/t31-,32-/m1/s1 Key: AQASRZOCERRGBL-ROJLCIKYBP
SMILES O(c1cc2c(cc1OC)[C@H](N(C)CC2)Cc6ccc(Oc3c(O)ccc(c3)C[C@@H]5c4c(cc(OC)c(OC)c4)CCN5C)cc6)C
Properties
Chemical formula	C38H44N2O6
Molar mass	624.778 g·mol−1
Density	1.186 g/mL
Melting point	115 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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