Delphinine

Delphinine
Names
	Other names 8-(Acetyloxy)-13-hydroxy-1,6,16-trimethoxy-4-(methoxymethyl)-20-methylaconitan-14-yl benzoate
Identifiers
CAS Number	561-07-9 ;
3D model (JSmol)	Interactive image; Interactive image;
ChemSpider	390329 ;
ECHA InfoCard	100.008.377
PubChem CID	441726;
UNII	IN41I78D7R ;
CompTox Dashboard (EPA)	DTXSID50971478 ;
	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 Key: REVYTWNGZDPRKE-UWZYQZSNSA-N ; 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;
	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;
Properties
Chemical formula	C33H45NO9
Molar mass	599.712
Appearance	colorless solid
Melting point	197 to 199 °C (387 to 390 °F; 470 to 472 K)
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Toxic
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Delphinine is a toxic diterpenoid alkaloid found in plants from the Delphinium (larkspur) and Atragene (a clematis) genera, both in the family Ranunculaceae.^[1] Delphinine is the principal alkaloid found in Delphinium staphisagria seeds – at one time, under the name stavesacre, a very well known herbal treatment for body lice.^[2] It is related in structure and has similar effects to aconitine, acting as an allosteric modulator of voltage gated sodium channels,^[3] and producing low blood pressure, slowed heart rate and abnormal heart rhythms. These effects make it highly poisonous (LD₅₀ 1.5–3.0 mg/kg in rabbit and dog; frogs are ~10x more susceptible).^[4] While it has been used in some alternative medicines (e.g. in herbal medicine^[5]^[6]), most of the medical community does not recommend using it due to its extreme toxicity.

^ Harbourne JB, Baxter H, eds. (1993). Phytochemical Dictionary. London: Taylor & Francis. p. 148.
^ "A Modern Herbal | Stavesacre".
^ 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. PMC 5001567. PMID 18201930.
^ Benn MH, Jacyno JM (1983). Pelletier SW (ed.). "Chapter 4". The Alkaloids: Chemical and Biological Perspectives. 1. New York: Wiley: 153–210.
^ Desai HK, Hart BP, Caldwell RW, Jianzhong-Huang JH, Pelletier SW (June 1998). "Certain norditerpenoid alkaloids and their cardiovascular action". Journal of Natural Products. 61 (6): 743–8. doi:10.1021/np970499j. PMID 9644057.
^ Díaz JG, Ruiz JG, de La Fuente G (August 2000). "Alkaloids from Delphinium staphisagria". Journal of Natural Products. 63 (8): 1136–9. doi:10.1021/np990453l. PMID 10978212.