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[[Category:Nitrogen heterocycles]]
[[Category:Nitrogen heterocycles]]
[[Category:Tyrosine hydroxylase inhibitors]]
[[Category:Tyrosine hydroxylase inhibitors]]
[[Category:Oxygen heterocycles]]
[[Category:Benzodioxoles]]
[[Category:Heterocyclic compounds (4 or more rings)]]
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Revision as of 14:56, 9 August 2017

Bulbocapnine
Names
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.511 Edit this at Wikidata
  • InChI=1S/C19H19NO4/c1-20-6-5-11-8-14-19(24-9-23-14)17-15(11)12(20)7-10-3-4-13(22-2)18(21)16(10)17/h3-4,8,12,21H,5-7,9H2,1-2H3/t12-/m0/s1 checkY
    Key: LODGIKWNLDQZBM-LBPRGKRZSA-N checkY
  • InChI=1/C19H19NO4/c1-20-6-5-11-8-14-19(24-9-23-14)17-15(11)12(20)7-10-3-4-13(22-2)18(21)16(10)17/h3-4,8,12,21H,5-7,9H2,1-2H3/t12-/m0/s1
    Key: LODGIKWNLDQZBM-LBPRGKRZBH
  • O1c4c(OC1)c3c2c(O)c(OC)ccc2C[C@H]5c3c(c4)CCN5C
Properties
C19H19NO4
Molar mass 325.36 g/mol
Melting point 201 to 203 °C (394 to 397 °F; 474 to 476 K) racemate 213-214 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

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] Experiments were used in MKULTRA. [6]

In literature

In television

  • The drug's use to treat Mayor Kane's father-in-law and predecessor is a plot point in season 2 of the TV series Boss, e.g., in episodes s2.e8 ("Consequences"; October 5, 2012) and s2.e9 ("Church"; October 12, 2012).

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. doi:10.1016/s0304-3940(98)00148-7. 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.
  6. ^ "CIA Revelations: Behavior Control" (PDF). Radio TV Reports. ABC News. 20 July 1977. Retrieved 24 January 2017.


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