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Brucine

From Wikipedia, the free encyclopedia
Poisonous alkaloid similar to strychnine
Not to be confused withBrucite.
Brucine
Names
IUPAC name
2,3-Dimethoxystrychnidin-10-one
Systematic IUPAC name
(4bR,4b1S,7aS,8aR,8a1R,12aS)-2,3-Dimethoxy-4b1,5,6,7a,8,8a,8a1,11,12a,13-decahydro-14H-12-oxa-7,14a-diaza-7,9-methanocyclohepta[cd]cyclopenta[g]fluoranthen-14-one
Other names
2,3-Dimethoxystrychnine
10,11-Dimethoxystrychnine
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard100.006.014Edit this at Wikidata
EC Number
  • 206-614-7
KEGG
RTECS number
  • EH8925000
UNII
UN number1570
  • InChI=1S/C23H26N2O4/c1-27-16-8-14-15(9-17(16)28-2)25-20(26)10-18-21-13-7-19-23(14,22(21)25)4-5-24(19)11-12(13)3-6-29-18/h3,8-9,13,18-19,21-22H,4-7,10-11H2,1-2H3/t13-,18-,19-,21-,22-,23+/m0/s1 checkY
    Key: RRKTZKIUPZVBMF-IBTVXLQLSA-N checkY
  • InChI=1/C23H26N2O4/c1-27-16-8-14-15(9-17(16)28-2)25-20(26)10-18-21-13-7-19-23(14,22(21)25)4-5-24(19)11-12(13)3-6-29-18/h3,8-9,13,18-19,21-22H,4-7,10-11H2,1-2H3/t13-,18-,19-,21-,22-,23+/m0/s1
    Key: RRKTZKIUPZVBMF-IBTVXLQLBR
  • O=C7N2c1cc(OC)c(OC)cc1[C@@]64[C@@H]2[C@@H]3[C@@H](OC/C=C5\[C@@H]3C[C@@H]6N(CC4)C5)C7
Properties
C23H26N2O4
Molar mass394.471 g·mol−1
Melting point178 °C (352 °F; 451 K)
Hazards
GHS labelling:
GHS06: Toxic
Danger
H300,H330,H412
P260,P264,P270,P271,P273,P284,P301+P310,P304+P340,P310,P320,P321,P330,P403+P233,P405,P501
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Chemical compound

Brucine is analkaloid closely related tostrychnine, most commonly found in theStrychnos nux-vomica tree. Brucine poisoning is rare, since it is usually ingested with strychnine, and strychnine is moretoxic than brucine. Inchemical synthesis, it can be used as a tool forstereospecific chemical syntheses.

Brucine's name derives from this of the genusBrucea, named afterJames Bruce who brought backBrucea antidysenterica from Ethiopia.

History

[edit]

Brucine was discovered in 1819 by the French chemistPelletier and the French pharmacistCaventou in thebark of theStrychnos nux-vomica tree.[1] While itschemical structure was not deduced until much later, it was determined that it was closely related to strychnine in 1884 when the chemist Hanssen converted both strychnine and brucine into the same molecule.[2]

Identification

[edit]

Brucine can be detected and quantified usingliquid chromatography-mass spectrometry.[3] Historically, brucine was distinguished from strychnine by its reactivity towardchromic acid.[4]

Applications

[edit]

Chemical applications

[edit]

Since brucine is a largechiral molecule, it has been used inchiral resolution. Fisher first reported its use as a resolving agent in 1899, and it was the first natural product used as anorganocatalyst in a reaction resulting in anenantiomeric enrichment byMarckwald, in 1904.[5] Its bromide salt has been used as thestationary phase inHPLC to selectively bind one of two anionic enantiomers.[6] Brucine has also been used for fractional crystallization inacetone to resolve dihydroxyfatty acids,[7] as well as diarylcarbinols.[8] If formic acid is added to a mixture of brucine andpotassium nitrate, its color instantly turns red. This reaction has been used for the direct colorimetric detection ofnitrates.[9]

Medical applications

[edit]

While brucine has been shown to have goodanti-tumor effects, on bothhepatocellular carcinoma[10] andbreast cancer,[11] its narrowtherapeutic window has limited its use as a treatment forcancer.

Brucine is also used intraditional Chinese medicine as ananti-inflammatory andanalgesic agent,[12] as well as in someAyurveda andhomeopathy drugs.[13]

Alcohol denaturant

[edit]

Brucine is one of the many chemicals used as adenaturant to makealcohol unfit for human consumption.[14]

Cultural references

[edit]

One of the most famous cultural references to brucine occurs inThe Count of Monte Cristo, the novel by French authorAlexandre Dumas. In a discussion ofmithridatism, Monte Cristo states:

“Well, suppose, then, that this poison was brucine, and you were to take a milligramme the first day, two milligrams the second day, and so on…at the end of a month, when drinking water from the same carafe, you would kill the person who drank with you, without your perceiving…that there was any poisonous substance mingled with this water.”[15]

Brucine is also mentioned in the 1972 version ofThe Mechanic, in which the hitman Steve McKenna betrays his mentor, ageing hitman Arthur Bishop, using a celebratory glass of wine spiked with brucine, leaving Bishop to die of an apparent heart attack.[16]

Such fictions run contrary to reality in the very properties which make brucine useful as a denaturant, and useless as a covert poison. While being only about one-eighth as toxic as strychnine, its threshold ofbitterness occurs at 69 % greaterdilution. A drink laden with brucine, overwhelmingly bitter at far belowlethal concentration, would cause an intended victim to gag on the first sip.

Safety

[edit]

Brucine intoxication occurs very rarely, since it is usually ingested with strychnine. Symptoms of brucine intoxication include musclespasms,convulsions,rhabdomyolysis, andacute kidney injury. Brucine’s mechanism of action closely resembles that ofstrychnine. It acts as anantagonist atglycine receptors and paralyzesinhibitory neurons.

The probablelethal dose of brucine in adults is 1 g.[17] In other animals, theLD50 varies considerably.

AnimalRoute of entryLD50[18]
MouseSubcutaneous60 mg/kg
RatIntraperitoneal91 mg/kg
RabbitOral4 mg/kg
Brucine's mechanism of action
Brucine's mechanism of action

References

[edit]
  1. ^Wormley, T (1869).Micro-chemistry of poisons including their physiological, pathological, and legal relations: Adapted to the use of the medical jurist, physician, and general chemist. New York: W. Wood.
  2. ^Buckingham, J (2007).Bitter Nemesis: The Intimate History of Strychnine. CRC Press. p. 225.
  3. ^Teske, J; Weller, J; Albrecht, U; Fieguth, A (2011)."Fatal Intoxication Due to Brucine".Journal of Analytical Toxicology.35 (4):248–253.doi:10.1093/anatox/35.4.248.PMID 21513620.
  4. ^Glasby, J. (1975).Encyclopedia of the alkaloids. New York: Plenum Press. p. 214.ISBN 9780306308451.
  5. ^Koskinen, A (1993).Asymmetric synthesis of natural products. Chichester: J. Wiley. pp. 17,28–29.
  6. ^Zarbua, K; Kral, V (2002). "Quaternized brucine as a novel chiral selector".Tetrahedron: Asymmetry.13 (23):2567–2570.doi:10.1016/s0957-4166(02)00715-2.
  7. ^Malkar, N; Kumar, V (1998). "Optical resolution of (±)-Threo-9,10,16-trihydroxy hexadecanoic acid using (−)brucine".Journal of the American Oil Chemists' Society.75 (10):1461–1463.doi:10.1007/s11746-998-0202-9.S2CID 83662051.
  8. ^Toda, F; Tanaka, K; Koshiro, K (1991). "A New Preparative Method for Optically Active Diarylcarbinols".Tetrahedron: Asymmetry.2 (9):873–874.doi:10.1016/s0957-4166(00)82198-9.
  9. ^Baker, Aaron Sidney (1967-05-01)."Colorimetric determination of nitrate in soil and plant extracts with brucine".ACS Publications.doi:10.1021/jf60153a004. Retrieved2025-03-01.
  10. ^Qin, J (2012)."Anti-Tumor Effects of Brucine Immune-Nanoparticles on Hepatocellular Carcinoma".International Journal of Nanomedicine.7:369–379.doi:10.2147/IJN.S27226.PMC 3273973.PMID 22334771.
  11. ^Serasanambati, M; Chilakapati, S; Vanagavaragu, J; Cilakapati, D (2014)."Inhibitory effect of gemcitabine and brucine on MDA MB-231 human breast cancer cells".International Journal of Drug Delivery.6. Archived fromthe original on 2016-03-04. Retrieved2015-05-02.
  12. ^Zhang, J; Wang, S; Chen, X; Zhide, H; Xiao, M (2003). "Capillary Electrophorese with Field-Enhanced Stacking for Rapid and Sensitive Determination of Strychnine and Brucine".Analytical and Bioanalytical Chemistry.376 (2):210–213.doi:10.1007/s00216-003-1852-y.PMID 12692702.S2CID 7832819.
  13. ^Rathi, A; Srivastava, N; Khatoon, S; Rawat, A (2008). "TLC Determination of Strychnine and Brucine of Strychnos nun vomica in Ayurveda and Homeopathy Drugs".Chromatographia.67 (7–8):607–613.doi:10.1365/s10337-008-0556-z.S2CID 94626190.
  14. ^"List of denaturants authorized for denatured spirits".www.law.cornell.edu. Cornell Law School. 30 August 2016. Retrieved2019-08-24.
  15. ^Dumas, Alexandre (1845).The Count of Monte Cristo. Feedbooks. p. 622.
  16. ^"Synopsis for The Mechanic".IMDb. Retrieved30 April 2015.
  17. ^Gosselin, R. E.; Smith, R. P.; Hodge, H. C. (1984).Clinical Toxicology of Commercial Products (5 ed.). Baltimore/London: Williams & Wilkins.
  18. ^"Brucine".Toxnet. NIH. Retrieved2018-10-07.

External links

[edit]
Wikisource has the text of the1911Encyclopædia Britannica article "Brucine".
Receptor
(ligands)
GlyRTooltip Glycine receptor
NMDARTooltip N-Methyl-D-aspartate receptor
Transporter
(blockers)
GlyT1Tooltip Glycine transporter 1
GlyT2Tooltip Glycine transporter 2
Authority control databases: NationalEdit this at Wikidata
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