Delphinine

Delphinine: Delphinine

Identifiers

CAS number 561-07-9

PubChem 441726

ChemSpider 390329^Y

UNII IN41I78D7R^Y

Jmol-3D images Image 1
Image 2

SMILES

CC(=O)O[C@]12C[C@@H]([C@]3(C[C@H]([C@@H]1[C@H]3OC(=O)C4=CC=CC=C4)[C@]56[C@H](CC[C@@]7([C@H]5[C@H]([C@H]2C6N(C7)C)OC)COC)OC)O)OC
O=C(O[C@H]5[C@]3(O)C[C@H]4[C@@]16C2N(C)C[C@]([C@H]1[C@@H](OC)[C@@H]2[C@@](OC(=O)C)(C[C@@H]3OC)[C@H]45)(COC)CC[C@@H]6OC)c7ccccc7

InChI

InChI=1S/C33H45NO9/c1-18(35)43-32-15-22(40-5)31(37)14-20(23(32)28(31)42-29(36)19-10-8-7-9-11-19)33-21(39-4)12-13-30(17-38-3)16-34(2)27(33)24(32)25(41-6)26(30)33/h7-11,20-28,37H,12-17H2,1-6H3/t20-,21+,22+,23-,24+,25+,26-,27?,28-,30+,31+,32-,33+/m1/s1^Y
Key: REVYTWNGZDPRKE-UWZYQZSNSA-N^Y
InChI=1/C33H45NO9/c1-18(35)43-32-15-22(40-5)31(37)14-20(23(32)28(31)42-29(36)19-10-8-7-9-11-19)33-21(39-4)12-13-30(17-38-3)16-34(2)27(33)24(32)25(41-6)26(30)33/h7-11,20-28,37H,12-17H2,1-6H3/t20-,21+,22+,23-,24+,25+,26-,27?,28-,30+,31+,32-,33+/m1/s1
Key: REVYTWNGZDPRKE-UWZYQZSNBH

Properties

Molecular formula C₃₃H₄₅NO₉

Molar mass 599.712

Melting point
197-199 °C

Hazards

Main hazards Toxic

Y (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Delphinine is a toxic alkaloid (LD₅₀ 1.5 mg/kg approx) found in plants from the Delphinium family. It is related in structure and has similar effects to aconitine, acting as an allosteric modulator of voltage gated sodium channels,^[1] and producing hypotension, bradycardia and cardiac arrythmia. These effects make it highly poisonous, but in very small doses it has some uses in herbal medicine.^[2]^[3]

References

^ Turabekova MA, Rasulev BF, Levkovich MG, Abdullaev ND, Leszczynski J (April 2008). "Aconitum and Delphinium sp. alkaloids as antagonist modulators of voltage-gated Na+ channels. AM1/DFT electronic structure investigations and QSAR studies". Computational Biology and Chemistry 32 (2): 88–101. doi:10.1016/j.compbiolchem.2007.10.003. PMID 18201930.

^ Desai HK, Hart BP, Caldwell RW, Jianzhong-Huang JH, Pelletier SW. Certain norditerpenoid alkaloids and their cardiovascular action. Journal of Natural Products. 1998 Jun 26;61(6):743-8. PMID 9644057

^ Díaz JG, Ruiz JG, de La Fuente G. Alkaloids from Delphinium staphisagria. Journal of Natural Products. 2000 Aug;63(8):1136-9. PMID 10978212

Categories:
Plant toxins
Alkaloids
Benzoates
Alcohols
Ethers
Acetate esters

Delphinine


Identifiers
CAS number	561-07-9
PubChem	441726
ChemSpider	390329^Y
UNII	IN41I78D7R^Y
Jmol-3D images	Image 1 Image 2
SMILES CC(=O)O[C@]12C[C@@H]([C@]3(C[C@H]([C@@H]1[C@H]3OC(=O)C4=CC=CC=C4)[C@]56[C@H](CC[C@@]7([C@H]5[C@H]([C@H]2C6N(C7)C)OC)COC)OC)O)OC O=C(O[C@H]5[C@]3(O)C[C@H]4[C@@]16C2N(C)C[C@]([C@H]1[C@@H](OC)[C@@H]2[C@@](OC(=O)C)(C[C@@H]3OC)[C@H]45)(COC)CC[C@@H]6OC)c7ccccc7
InChI InChI=1S/C33H45NO9/c1-18(35)43-32-15-22(40-5)31(37)14-20(23(32)28(31)42-29(36)19-10-8-7-9-11-19)33-21(39-4)12-13-30(17-38-3)16-34(2)27(33)24(32)25(41-6)26(30)33/h7-11,20-28,37H,12-17H2,1-6H3/t20-,21+,22+,23-,24+,25+,26-,27?,28-,30+,31+,32-,33+/m1/s1^Y Key: REVYTWNGZDPRKE-UWZYQZSNSA-N^Y InChI=1/C33H45NO9/c1-18(35)43-32-15-22(40-5)31(37)14-20(23(32)28(31)42-29(36)19-10-8-7-9-11-19)33-21(39-4)12-13-30(17-38-3)16-34(2)27(33)24(32)25(41-6)26(30)33/h7-11,20-28,37H,12-17H2,1-6H3/t20-,21+,22+,23-,24+,25+,26-,27?,28-,30+,31+,32-,33+/m1/s1 Key: REVYTWNGZDPRKE-UWZYQZSNBH
Properties
Molecular formula	C₃₃H₄₅NO₉
Molar mass	599.712
Melting point	197-199 °C
Hazards
Main hazards	Toxic
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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Delphinine — Del phi*nine (?; 104), n. [Cf. F. delphinine.] (Chem.) A poisonous alkaloid extracted from the stavesacre ({Delphinium staphisagria}), as a colorless amorphous powder. [1913 Webster] … The Collaborative International Dictionary of English
delphinine — [del′fə nēn΄, del′fənin] n. [ DELPHINIUM + INE3] a poisonous, white, crystalline alkaloid, C33H45NO9, found in the seeds of certain larkspurs … English World dictionary
delphinine — /del feuh neen , nin/, n. Chem. a bitter, poisonous, crystalline alkaloid, C33H45NO9, obtained from various species of larkspur, esp. Delphinium staphisagria. [1820 30; DELPHIN(IUM) + INE2] * * * … Universalium
delphinine — 1. noun A type of toxic alkaloid found in some plants in the Delphinium family, which can also be used medicinally. 2. adjective Characteristic of dolphins … Wiktionary
delphinine — A toxic alkaloid, an aconine derivative, from Delphinium staphisagria; it resembles aconitine in its action and chemical structure. * * * del·phi·nine del fə .nēn, nən n a poisonous crystalline alkaloid C33H45NO9 obtained esp. from seeds of the… … Medical dictionary
delphinine — (dèl fi ni n ) s. f. Terme de chimie. Alcaloïde découvert dans la staphisaigre, dont il est le principe actif. ÉTYMOLOGIE Delphinium … Dictionnaire de la Langue Française d'Émile Littré
delphinine — n. poisonous alkaloid (Chemistry) … English contemporary dictionary
delphinine — del·phi·nine … English syllables
delphinine — /ˈdɛlfənin/ (say delfuhneen), / naɪn/ (say nuyn) noun a bitter, poisonous, crystalline alkaloid obtained from various species of delphinium, especially Delphinium staphisagria. {delphin(ium) + ine2} …
delphinine — ˌnēn, nə̇n noun ( s) Etymology: New Latin Delphinium (genus name of Delphinium staphisagria) + English ine : a poisonous crystalline alkaloid C33H45NO9 obtained especially from seeds of the stavesacre … Useful english dictionary

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Delphinine

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