Bulbocapnine

Chemical compound From Wikipedia, the free encyclopedia

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 Corydalis caseana) 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][non-primary source needed] 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]

Other namesBulbokaprin
CAS Number
Quick facts Clinical data, Other names ...
Bulbocapnine
Clinical data
Other namesBulbokaprin
Identifiers
  • (12S)-17-methoxy-11-methyl-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14(19),15,17-hexaen-18-ol
CAS Number
PubChem CID
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KEGG
ChEBI
ChEMBL
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ECHA InfoCard100.005.511 Edit this at Wikidata
Chemical and physical data
FormulaC19H19NO4
Molar mass325.364 g·mol−1
3D model (JSmol)
Melting point201 to 203 °C (394 to 397 °F)
Racemate 213–214 °C
  • O1c4c(OC1)c3c2c(O)c(OC)ccc2C[C@H]5c3c(c4)CCN5C
  • 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
  • Key:LODGIKWNLDQZBM-LBPRGKRZSA-N
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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 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

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