Bulbocapnine

Chembox new
Name = Bulbocapnine
ImageFile = Bulbocapnine skeletal.svg
ImageName =
IUPACName = ("S")-6,7,7a,8-tetrahydro-11-methoxy-7-methyl-5"H"-benzo ["g"] -1,3-benzodioxolo- [6,5,4-"de"] quinolin-2-ol
Section1 = Chembox Identifiers
CASNo = 298-45-3
SMILES = Oc3c-2c(ccc3OC)CC1c4c-2c5OCOc5cc4CCN1C
Section2 = Chembox Properties
Formula = C₂₀H₂₁NO₄
MolarMass = 325.36 g/mol
Density =
MeltingPt = 201-203 °C, racemate 213-214 °C
BoilingPt =

Bulbocapnine is an alkaloid found in "Corydalis" and "Dicentra", herbs in the family Fumariaceae that can cause fatal poisoning in sheep and cattle. It has been shown to act as an acetylcholinesterase inhibitor, [Adsersen A, Kjølbye A, Dall O, Jäger AK. Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Corydalis cava Schweigg. & Kort. "Journal of Ethnopharmacology". 2007 Aug 15;113(1):179-82. PMID 17574358] and inhibits biosynthesis of dopamine via inhibition of the enzyme tyrosine hydroxylase. [Zhang YH, Shin JS, Lee SS, Kim SH, Lee MK. Inhibition of tyrosine hydroxylase by bulbocapnine. "Planta Medica". 1997 Aug;63(4):362-3. PMID 9270381] [Shin JS, Kim KT, Lee MK. Inhibitory effects of bulbocapnine on dopamine biosynthesis in PC12 cells. "Neuroscience Letters". 1998 Mar 20;244(3):161-4. PMID 9593514]

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" [ [http://www.mercksource.com/pp/us/cns/cns_hl_dorlands.jspzQzpgzEzzSzppdocszSzuszSzcommonzSzdorlandszSzdorlandzSzdmd_b_26zPzhtm Dorlands Medical Dictionary at Merck] ] . The psychiatrist Robert Heath carried out experiments on prisoners at the Louisiana State Penitentiary using bulbocapnine to induce stupor. [Scheflin, A.W. & Opton, E.M. (1978) "The Mind Manipulators: a non-fiction account." (Paddington Press: New York) ISBN 0448229773 pp. 314-315.] .

The author William Burroughs references the drug in his book "Naked Lunch", where the fictional Dr. Benway uses it to induce obedience in torture victims.

ee also

*Apomorphine
*Glaucine
*Nuciferine
*Pukateine
*Stepholidine
*Tetrahydropalmatine

References