Bulbocapnine

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Bulbocapnine
IUPAC name

(S)-6,7,7a,8-tetrahydro-11-methoxy-7-methyl-5H- benzo[g]-1,3-benzodioxolo-[6,5,4-de]quinolin-2-ol

Identifiers
CAS number 298-45-3 YesY
PubChem 12441
ChemSpider 11934 YesY
ChEMBL CHEMBL157912 YesY
Jmol-3D images {{#if:O1c4c(OC1)c3c2c(O)c(OC)ccc2C[C@H]5c3c(c4)CCN5C|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.

See also

References

  1. ↑ Adsersen, A.; Kjølbye, A.; Dall, O.; Jäger, A. K. (Aug 2007). "Acetylcholinesterase and Butyrylcholinesterase Inhibitory Compounds from Corydalis cava Schweigg. & Kort.". Journal of Ethnopharmacology 113 (1): 179–182. doi:10.1016/j.jep.2007.05.006. PMID 17574358. 
  2. ↑ Zhang, Y. H.; Shin, J. S.; Lee, S. S.; Kim, S. H.; Lee, M. K. (Aug 1997). "Inhibition of Tyrosine Hydroxylase by Bulbocapnine". Planta Medica 63 (4): 362–363. doi:10.1055/s-2006-957702. PMID 9270381. 
  3. ↑ Shin, J. S.; Kim, K. T.; Lee, M. K. (Mar 1998). "Inhibitory Effects of Bulbocapnine on Dopamine Biosynthesis in PC12 Cells". Neuroscience Letters 244 (3): 161–164. PMID 9593514. 
  4. ↑ "Dorlands Medical Dictionary at Merck". 
  5. ↑ Scheflin, A. W.; Opton, E. M. (1978). The Mind Manipulators: A non-fiction Account. New York: Paddington Press. pp. 314–315. ISBN 0-448-22977-3. 
Class
Substrate
Oxidoreductase (EC 1)
Transferase (EC 2)
Hydrolase (EC 3)
Lyase (EC 4)
  • 4.1 Dopa decarboxylase


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