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Bulbocapnine information


Bulbocapnine
Clinical data
Other namesBulbokaprin
Identifiers
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
CAS Number
  • 298-45-3
PubChem CID
  • 12441
ChemSpider
  • 11934
UNII
  • O0TGI865QO
KEGG
  • C09367
ChEBI
  • CHEBI:3211
ChEMBL
  • ChEMBL157912
CompTox Dashboard (EPA)
  • DTXSID20183940 Edit this at Wikidata
ECHA InfoCard100.005.511 Edit this at Wikidata
Chemical and physical data
FormulaC19H19NO4
Molar mass325.364 g·mol−1
3D model (JSmol)
  • Interactive image
Melting point201 to 203 °C (394 to 397 °F)
Racemate 213–214 °C
SMILES
  • O1c4c(OC1)c3c2c(O)c(OC)ccc2C[C@H]5c3c(c4)CCN5C
InChI
  • 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

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] 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]

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]

  1. ^ CRC World Dictionary of Medicinal and Poisonous Plants: Common Names ... p.1142.
  2. ^ Adsersen A, Kjølbye A, Dall O, Jäger AK (August 2007). "Acetylcholinesterase and butyrylcholinesterase inhibitory compounds from Corydalis cava Schweigg. & Kort". Journal of Ethnopharmacology. 113 (1): 179–182. doi:10.1016/j.jep.2007.05.006. PMID 17574358.
  3. ^ Zhang YH, Shin JS, Lee SS, Kim SH, Lee MK (August 1997). "Inhibition of tyrosine hydroxylase by bulbocapnine". Planta Medica. 63 (4): 362–363. doi:10.1055/s-2006-957702. PMID 9270381. S2CID 29474171.
  4. ^ Shin JS, Kim KT, Lee MK (March 1998). "Inhibitory effects of bulbocapnine on dopamine biosynthesis in PC12 cells". Neuroscience Letters. 244 (3): 161–164. doi:10.1016/s0304-3940(98)00148-7. PMID 9593514. S2CID 2415472.
  5. ^ Lashuel HA, Hartley DM, Balakhaneh D, Aggarwal A, Teichberg S, Callaway DJ (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. 277 (45): 42881–42890. doi:10.1074/jbc.M206593200. PMID 12167652.
  6. ^ "Dorlands Medical Dictionary at Merck". Archived from the original on 2008-03-01. Retrieved 2006-12-25.
  7. ^ Scheflin AW, Opton EM (1978). The Mind Manipulators: A non-fiction Account. New York: Paddington Press. pp. 314–315. ISBN 0-448-22977-3.
  8. ^ "CIA Revelations: Behavior Control" (PDF). Radio TV Reports. ABC News. 20 July 1977. Archived from the original (PDF) on January 23, 2017. Retrieved 24 January 2017.

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Bulbocapnine

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Corydalis

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Corydalis cava and some other tuberous species contain the alkaloid bulbocapnine, which is occasionally used in medicine but scientific evidence is lacking...

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Catalepsy

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naïve young man falls foul of a criminal gang who employ a curious, bulbocapnine-like drug which induces catalepsy, as a result of which he narrowly escapes...

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Robert Galbraith Heath

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heterosexuality using DBS. Heath also experimented with psychosurgery, the drug bulbocapnine to induce stupor, and LSD, using African-American prisoners in the Louisiana...

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Glaucine

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as "head candy". Aporphine Boldine Nuciferine Apomorphine Pukateine Bulbocapnine Drotaverine Nantenine Stepholidine Tetrahydropalmatine Lapa GB, Sheichenko...

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Aporphine alkaloids

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(heart flowers), and also in the horn poppy. Apoglaziovine Apomorphine Bulbocapnine Corydine Domesticine Glaucine Isoboldine Isothebaine Nuciferine The aporphine...

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Aporphine

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D2 antagonist with a Ki of 527nM. Aporphine and its related alkaloids bulbocapnine, boldine, glaucine, and corytuberine are antipsychotic, exert naloxone-reversible...

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Tobacco

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Inhibitors: 2-Hydroxyestradiol 2-Hydroxyestrone 3-Iodotyrosine Aquayamycin Bulbocapnine Metirosine Oudenone DBHTooltip Dopamine beta-monooxygenase Substrates→Products:...

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Caffeine

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Corydalis cava

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Corydalis cava and some other tuberous species contain the alkaloid bulbocapnine, which is occasionally used in medicine but for which scientific evidence...

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Diphenhydramine

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Botulinum toxin

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List of dopaminergic drugs

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Tuaminoheptane (tuamine) 3,4-Dihydroxystyrene 3-Iodotyrosine • Aquayamycin • Bulbocapnine • Metirosine • Oudenone Benserazide • Carbidopa • Genistein • Methyldopa...

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In a Glass Darkly

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(fictional) drug, however, are curiously reminiscent of those of the alkaloid bulbocapnine, which occurs in the medicinal herb Corydalis cava, a plant known to...

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Methylene blue

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Choline

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Carbendazim

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Donepezil

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Anticholinergic

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Nuciferine

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apomorphine and other aporphine derivatives. Apomorphine Aporphine Glaucine Bulbocapnine Nantenine Pukateine Stepholidine Tetrahydropalmatine Seligman, Sian (2023-01-13)...

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Pyridostigmine

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Ethylcholine mustard

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Harmala alkaloid

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Dicyclohexyl phosphorofluoridate

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Monoamine oxidase inhibitor

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Neostigmine

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Entacapone

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