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
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.511 Edit this at Wikidata
EC Number
  • 206-061-1
KEGG
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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
Chemical formula
 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  (what is checkY☒N ?)
Infobox references

Bulbocapnine is an alkaloid found in Corydalis (notably the European species C. cava) and Dicentra, genera of the plant family Fumariaceae which have caused (notably the American species ) the fatal poisoning of sheep and cattle.[1] It has been shown to act as an acetylcholinesterase inhibitor,[2] and inhibits biosynthesis of dopamine via inhibition of the enzyme tyrosine hydroxylase.[3][4] 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.[5] 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".[6]

A psychiatrist at Tulane University named Robert Heath carried out experiments on prisoners at the Louisiana State Penitentiary using bulbocapnine to induce stupor.[7] This work at Tulane inspired, and was continued parallel to, experiments carried out at the behest of the Central Intelligence Agency. The bulbocapnine work Heath conducted for the government was one component of a large investigation into the potential of psychoactive compounds as aids to interrogation.[8]

Effects[]

It can induce catalepsy featuring the curious symptom of waxy flexibility[9] and the state produced by the drug has been compared to Akinetic mutism.[10][11]

In popular culture[]

In literature[]

  • The author William S. Burroughs references the drug in his book Naked Lunch (1959), in which the fictional Dr. Benway uses it to induce obedience in torture victims.

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. ^ CRC World Dictionary of Medicinal and Poisonous Plants: Common Names ... p.1142.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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. S2CID 2415472.
  5. ^ 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.
  6. ^ "Dorlands Medical Dictionary at Merck". Archived from the original on 2008-03-01. Retrieved 2006-12-25.
  7. ^ 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.
  8. ^ "CIA Revelations: Behavior Control" (PDF). Radio TV Reports. ABC News. 20 July 1977. Retrieved 24 January 2017.
  9. ^ Loizzo, A.; de Carolis, A. Scotti; Longo, V. G. (September 1971). "Studies on the central effects of bulbocapnine". Psychopharmacologia. 22 (3): 234–249. doi:10.1007/BF00401786. PMID 5316197. S2CID 41534659.
  10. ^ Johnson, John (1984). "Stupor and akinetic mutism". Contemporary Neurology. pp. 96–102. doi:10.1016/B978-0-407-00308-8.50018-5. ISBN 978-0-407-00308-8.
  11. ^ Jong, Herman Holland de (1945). Experimental catatonia, a general reaction-form of the central nervous system and its implications for human pathology. The Williams & Wilkins Company. p. 6. OCLC 989851203.


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