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
298-45-3 YesY
ChEBI CHEBI:3211 N
ChEMBL ChEMBL157912 YesY
ChemSpider 11934 YesY
Jmol 3D model Interactive image
PubChem 12441
  • 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 YesY
    Key: LODGIKWNLDQZBM-LBPRGKRZSA-N YesY
  • 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 YesYN ?)
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]

In popular culture

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

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