Bulbocapnine

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Bulbocapnine
Bulbocapnine skeletal.svg
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
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).
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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.[citation needed] 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] Like apomorphine, it is reported to be an inhibitor of amyloid beta protein (Aβ) fiber formation, whose presence is a hallmark of Alzheimer's disease (AD). Bulbocapnine is thus a potential therapeutic under the amyloid hypothesis.[4]

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".[5] The psychiatrist Robert Heath carried out experiments on prisoners at the Louisiana State Penitentiary using bulbocapnine to induce stupor.[6] Experiments were used in MKULTRA.[7]

In popular culture[edit]

In literature[edit]

In television[edit]

  • 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[edit]

References[edit]

  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. ^ Lashuel HA, Hartley DM, Balakhaneh D, Aggarwal A, Teichberg S, Callaway DJ (November 2002). "New class of inhibitors of amyloid-beta fibril formation. Implications for the mechanism of pathogenesis in Alzheimer's disease". The Journal of Biological Chemistry. 277 (45): 42881–90. doi:10.1074/jbc.M206593200. PMID 12167652.
  5. ^ "Dorlands Medical Dictionary at Merck". Archived from the original on 2008-03-01. Retrieved 2006-12-25.
  6. ^ 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.
  7. ^ "CIA Revelations: Behavior Control" (PDF). Radio TV Reports. ABC News. 20 July 1977. Retrieved 24 January 2017.