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(S)-(+)-bulbocapnine

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(S)-(+)-bulbocapnine

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Also known as Bulbocapnine

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. It has been shown to act as an acetylcholinesterase inhibitor, and inhibits biosynthesis of dopamine via inhibition of the enzyme tyrosine hydroxylase. 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

Key facts

Drug.drug_name
Bulbocapnine
Drug.image
Bulbocapnine skeletal.svg
Drug.image_class
skin-invert-image
Drug.width
200px
Drug.image2
Bulbocapnine.png
Drug.image_class2
bg-transparent
Drug.width2
200px
Drug.CAS_number
298-45-3
Drug.PubChem
12441
Drug.ChemSpiderID
11934
Drug.UNII
O0TGI865QO
Drug.KEGG
C09367
Drug.ChEBI
3211
Drug.ChEMBL
157912
Drug.synonyms
Bulbokaprin
Drug.IUPAC_name
(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
Drug.C
19
Drug.H
19

via Wikipedia infobox

Chemical data

Formula
C19H19NO4
Molecular weight
325.4 g/mol
IUPAC name
(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
SMILES
CN1CCC2=CC3=C(C4=C2[C@@H]1CC5=C4C(=C(C=C5)OC)O)OCO3
InChIKey
LODGIKWNLDQZBM-LBPRGKRZSA-N
XLogP
2.9
Polar surface area
51.2 Ų
H-bond donors
1
H-bond acceptors
5
Formal charge
0

via PubChem

Drug data · ChEMBL

Molecule type
Small molecule

via ChEMBL · EBI

Wikidata facts

Mass
325.131
Show 5 more facts
chemical formula
C₁₉H₁₉NO₄
found in taxon
Corydalis cava
canonical SMILES
CN1CCC2=CC3=C(C4=C2C1CC5=C4C(=C(C=C5)OC)O)OCO3
isomeric SMILES
CN1CCC2=CC3=C(C4=C2[C@@H]1CC5=C4C(=C(C=C5)OC)O)OCO3
Commons category
Bulbocapnine
Sources (2)

via Wikidata · CC0

~2 min read

Encyclopedic overview

6 sections
Contents
  • Effects
  • In popular culture
  • In literature
  • In television
  • See also
  • 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 Corydalis caseana) the fatal poisoning of sheep and cattle. It has been shown to act as an acetylcholinesterase inhibitor, and inhibits biosynthesis of dopamine via inhibition of the enzyme tyrosine hydroxylase. 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. 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".

A psychiatrist at Tulane University named Robert Heath carried out experiments on prisoners at the Louisiana State Penitentiary using bulbocapnine to induce stupor. 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.

Excerpted from Wikipedia’s “(S)-(+)-bulbocapnine” article, available under the CC BY-SA 4.0 licence.

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