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Bulbocapnine

Chemical compound

Summary

Chemical compound

Field	Value
drug_name	Bulbocapnine
image	File:Bulbocapnine skeletal.svg
image_class	skin-invert-image
image2	File:Bulbocapnine.png
image_class2	bg-transparent
CAS_number	298-45-3
PubChem	12441
ChemSpiderID	11934
UNII	O0TGI865QO
KEGG	C09367
ChEBI	3211
ChEMBL	157912
synonyms	Bulbokaprin
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
C	19	H=19	N=1	O=4
SMILES	O1c4c(OC1)c3c2c(O)c(OC)ccc2C[C@H]5c3c(c4)CCN5C
StdInChI	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
StdInChIKey	LODGIKWNLDQZBM-LBPRGKRZSA-N
melting_point	201 to 203
melting_notes
Racemate 213–214 °C

| Drugs.com =

| elimination_half-life =

Racemate 213–214 °C

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.

Effects

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

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).

References

CRC World Dictionary of Medicinal and Poisonous Plants: Common Names ... p.1142.
(August 2007). "Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Corydalis cava Schweigg. & Kort". Journal of Ethnopharmacology.
(August 1997). "Inhibition of tyrosine hydroxylase by bulbocapnine". Planta Medica.
(March 1998). "Inhibitory effects of bulbocapnine on dopamine biosynthesis in PC12 cells". Neuroscience Letters.
(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.
"Dorlands Medical Dictionary at Merck".
(1978). "The Mind Manipulators: A non-fiction Account". Paddington Press.
(20 July 1977). "CIA Revelations: Behavior Control". Radio TV Reports.
(September 1971). "Studies on the central effects of bulbocapnine". Psychopharmacologia.
(1984). "Contemporary Neurology".
(1945). "Experimental catatonia, a general reaction-form of the central nervous system and its implications for human pathology". The Williams & Wilkins Company.

Wikipedia Source

This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page.

acetylcholinesterase-inhibitors aporphine-alkaloids alkaloids-found-in-papaveraceae phenol-ethers nitrogen-heterocycles tyrosine-hydroxylase-inhibitors heterocyclic-compounds-with-5-rings methylenedioxyphenethylamines plant-toxins methoxy-compounds toxicology

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