Bulbocapnine

Title: Bulbocapnine
CAS Registry Number: 298-45-3
CAS Name: (7aS)-6,7,7a,8-Tetrahydro-11-methoxy-7-methyl-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinolin-12-ol
Additional Names: 10-methoxy-1,2-(methylenedioxy)-6aa-aporphin-11-ol
Molecular Formula: C19H19NO4
Molecular Weight: 325.36
Percent Composition: C 70.14%, H 5.89%, N 4.30%, O 19.67%
Literature References: From root of Corydalis cava (L.) Schweigg. & Körte (C. tuberosa DC), Fumariaceae and Dicentra canadensis Walp., Papaveraceae. Isoln: Freund, Josephi, Ber. 25, 2411 (1892); Manske, Can. J. Res. 7, 258 (1932). Pharmacology and toxicity study: H. Molitar, J. Pharmacol. Exp. Ther. 56, 85 (1936). Structure: Gadamer, Chem. Ztg. 34, 1004 (1910). Configuration: Ayer, Taylor, J. Chem. Soc. 1956, 472; Corrodi, Hardegger, Helv. Chim. Acta 39, 889 (1956). Synthesis: Kikkawa, C.A. 54, 4649b (1960). Peripheral-dopamine-receptor blocking activity: R. G. Pendleton et al., Arch. Pharmacol. 289, 171 (1975).
Derivative Type: dl-Form
Properties: Columns, mp 213-214°. Absorption max: Brustier, C.A. 49, 12127b (1955).
Melting point: mp 213-214°
Derivative Type: l-Form
Properties: Columns, mp 202-203°. [a]D22 -239°.
Melting point: mp 202-203°
Optical Rotation: [a]D22 -239°
Derivative Type: d-Form
Properties: Columns, mp 201-203°. [a]D22 +231°. Practically insol in water, sol in alcohol, chloroform. LD50 s.c. in mice: 195 mg/kg (Molitar).
Melting point: mp 201-203°
Optical Rotation: [a]D22 +231°
Toxicity data: LD50 s.c. in mice: 195 mg/kg
Derivative Type: Methyl ether
Molecular Formula: C20H21NO4
Molecular Weight: 339.39
Percent Composition: C 70.78%, H 6.24%, N 4.13%, O 18.86%
Properties: Crystals from petr ether, mp 129°. [a]D20+260°. Absorption max: Girardet, J. Chem. Soc. 1931, 2630.
Melting point: mp 129°
Optical Rotation: [a]D20+260°
Bullvalene Bumadizon Bumetanide Bunaftine Bunamidine

Bulbocapnine
Bulbocapnine skeletal.svg
Identifiers
CAS number 298-45-3 YesY
PubChem 12441
ChemSpider 11934 YesY
ChEMBL CHEMBL157912 YesY
Jmol-3D images Image 1
Properties
Molecular formula C19H19NO4
Molar mass 325.36 g/mol
Melting point 201-203 °C, racemate 213-214 °C
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Bulbocapnine is an alkaloid found in Corydalis (Papaveraceae) and Dicentra, plants in the family Fumariaceae that can cause fatal poisoning in sheep and cattle. It has been shown to act as an acetylcholinesterase inhibitor,[1] and inhibits biosynthesis of dopamine via inhibition of the enzyme tyrosine hydroxylase.[2][3]

According to the Dorlands Medical Dictionary, it "inhibits the reflex and motor activities of striated muscle. It has been used in the treatment of muscular tremors and vestibular nystagmus".[4] The psychiatrist Robert Heath carried out experiments on prisoners at the Louisiana State Penitentiary using bulbocapnine to induce stupor.[5]

The author William S. Burroughs references the drug in his book Naked Lunch, in which the fictional Dr. Benway uses it to induce obedience in torture victims. The drug also briefly appears in the second season of the TV series Boss.