Dauricine

Dauricine: Dauricine

IUPAC name

4-((1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl)-2-(4-((1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl)phenoxy)phenol

Identifiers

CAS number 524-17-4

PubChem 73400

ChemSpider 66117

ChEMBL CHEMBL442717

Jmol-3D images Image 1

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

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

Properties

Molecular formula C₃₈H₄₄N₂O₆

Molar mass 624.76576

Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Dauricine is a calcium channel blocker. It is the main toxin that makes the North American vine Menispermum canadense (moonseed) poisonous (often fatally so).^[1]

References

^ "Menispermum canadense". Poisonous Plants of North Carolina, Alice B. Russell Department of Horticultural Science; James W. Hardin, Larry Grand, and Angela Fraser. North Carolina State University. http://www.ces.ncsu.edu/depts/hort/consumer/poison/Menisca.htm.

v · d · eChannel blocker: calcium channel blockers (C08)

Selective

Dihydropyridines ("-dipine")

Amlodipine^# • Aranidipine • Azelnidipine • Barnidipine • Benidipine • Cilnidipine • Clevidipine • Darodipine • Efonidipine • Felodipine • Isradipine • Lacidipine • Manidipine • Lercanidipine • Mepirodipine • Nicardipine • Nifedipine^# • Niludipin • Nilvadipine • Nimodipine • Nisoldipine • Nitrendipine • Oxodipine • Pranidipine • Ryodipine

Phenylalkylamines ("-pamil")

Anipamil • Devapamil • Emopamil • Falipamil • Gallopamil • Norverapamil • Verapamil

1-4 Benzothiazepines ("-tiazem")

Clentiazem • Diltiazem

Non-selective
Bepridil • Fendiline • Lidoflazine • Perhexiline

Other/ungrouped
Amrinone • Anandamide • Azimilide • Bencyclane • Berbamine • Bevantolol • Canadine • Carboxyamidotriazole • Caroverine • Cinnarizine • Conotoxins • Dauricine • Dimeditiapramine • Dotarizine • Enpiperate • Eperisone • Fantofarone • Fasudil • Fenamic acid • Flunarizine • Fostedil • Gabapentin • Lamotrigine • Magnesium sulfate • Manoalide • Mibefradil^‡ • Monatepil • Naftopidil • Niguldipine • Ochratoxin A • Octylonium • Osthol • Pinaverium • Piperidine • Pregabalin • Prenylamine • Risedronic acid • Sesamodil • Stepholidine • Terodiline • Tetrahydropalmatine • Tetrandrine • Tolfenamic acid • Tranilast • TROX-1 • Ziconotide

^#WHO-EM. ^‡Withdrawn from market. Clinical trials: ^†Phase III. ^§Never to phase III

M: VAS

anat(a:h/u/t/a/l,v:h/u/t/a/l)/phys/devp/cell/prot

noco/syva/cong/lyvd/tumr, sysi/epon, injr

proc, drug(C2s+n/3/4/5/7/8/9)

Categories:
Calcium channel blockers
Phenols
Phenol ethers
Tetrahydroisoquinolines
Biochemistry stubs

Dauricine

IUPAC name 4-((1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl)-2-(4-((1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-isoquinolinyl)methyl)phenoxy)phenol
Identifiers
CAS number	524-17-4
PubChem	73400
ChemSpider	66117
ChEMBL	CHEMBL442717
Jmol-3D images	Image 1
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
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
Properties
Molecular formula	C₃₈H₄₄N₂O₆
Molar mass	624.76576
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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Calcium channel blocker — A calcium channel blocker (CCB) is a chemical that disrupts the movement of calcium (Ca2+) through calcium channels.[1] CCB drugs devised to target neurons are used as antiepileptics. However, the most widespread clinical usage of calcium channel … Wikipedia
Verapamil — Systematic (IUPAC) name (RS) 2 (3,4 dimethoxyphenyl) 5 {[2 (3,4 dimethoxyphenyl)ethyl] (methyl)amino} 2 prop 2 ylpentanenitrile Clinical data Licence … Wikipedia
Amlodipine — Systematic (IUPAC) name … Wikipedia
Nifedipine — Systematic (IUPAC) name 3,5 dimethyl 2,6 dim … Wikipedia
Diltiazem — Systematic (IUPAC) name cis (+) [2 (2 dimethylaminoethyl) 5 (4 methoxyphenyl) 3 oxo 6 thia 2 azabicyclo[5.4.0]undeca 7,9, 11 trien 4 yl]ethanoate … Wikipedia
Felodipine — Systematic (IUPAC) name 3 ethyl 5 meth … Wikipedia
Nimodipine — Systematic (IUPAC) name 3 (2 methoxyethyl) 5 propan 2 yl 2,6 dimethyl 4 (3 nitrophenyl) 1,4 dihydropyridine 3,5 dicarboxylate Clinical data … Wikipedia
Menispermum canadense — Canadian Moonseed Scientific classification Kingdom: Plantae (unranked) … Wikipedia
Nilvadipine — Systematic (IUPAC) name 5 isopropyl 3 methyl 2 cyano 6 methyl 4 (3 nitrophenyl) 1,4 dihydropyridine 3,5 dicarboxylate Clinical data AHFS/D … Wikipedia
Nicardipine — Systematic (IUPAC) name 2 [benzyl(methyl)amino]ethyl methyl 2,6 dimethyl 4 (3 nitrophenyl) 1,4 dihydropyridine 3,5 dicarboxylate Clinical data AHFS/ … Wikipedia

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Dauricine

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