Delphinine

Title: Delphinine
CAS Registry Number: 561-07-9
CAS Name: (1a,6a,14a,16b)-1,6,16-Trimethoxy-4-(methoxymethyl)-20-methylaconitane-8,13,14-triol 8-acetate 14-benzoate
Molecular Formula: C33H45NO9
Molecular Weight: 599.71
Percent Composition: C 66.09%, H 7.56%, N 2.34%, O 24.01%
Literature References: A toxic alkaloid from seeds of Delphinium staphisagria L., Ranunculaceae. Isoln: Markwood, J. Am. Pharm. Assoc. 16, 928 (1927). Purification: Schneider, Arch. Pharm. 283, 283 (1950). Structure: Jacobs, Pelletier, J. Am. Chem. Soc. 78, 3542 (1956); Wiesner et al., Can. J. Chem. 47, 2734 (1969). Configuration: Wiesner et al., Tetrahedron Lett. 1959, no. 3, 12; 1960, no. 15, 23; Gilman, Marion, ibid. 1962, 923; Birnbaum et al., ibid. 1971, 867. Synthesis: Wiesner et al., Can. J. Chem. 50, 1925 (1972).
Properties: Orthorhombic, six-sided plates from alc, mp 197.5-199°. [a]D20 +25° (ethanol). Practically insol in water. Sol in 25 parts alcohol, 20 parts chloroform, 10 parts ether.
Melting point: mp 197.5-199°
Optical Rotation: [a]D20 +25° (ethanol)
Derivative Type: Hydrochloride
Molecular Formula: C33H45NO9.HCl
Molecular Weight: 636.17
Percent Composition: C 62.30%, H 7.29%, N 2.20%, O 22.63%, Cl 5.57%
Properties: Crystals, dec 214°.
Delsoline delta-Aminolevulinic Acid delta-Carotene Deltamethrin delta-Tocopherol

Delphinine
Delphinine.svg
Delphinine.gif
Identifiers
CAS number 561-07-9 YesY
PubChem 441726
ChemSpider 390329 YesY
UNII IN41I78D7R YesY
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C33H45NO9
Molar mass 599.712
Appearance colorless solid
Melting point 197–199 °C
Hazards
Main hazards Toxic
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
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 hypotension, bradycardia and cardiac arrhythmia. These effects make it highly poisonous (LD50 1.5–3.0 mg/kg in rabbit and dog; frogs are ~10x more susceptible),[4] but in very small doses it has some uses in herbal medicine.[5][6]