Poisonous alkaloid similar to strychnine
Brucine Names IUPAC name 2,3-Dimethoxystrychnidin-10-one
Systematic IUPAC name (4bR ,4b1 S ,7aS ,8aR ,8a1 R ,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 names2,3-Dimethoxystrychnine
Identifiers ChEBI ChEMBL ChemSpider ECHA InfoCard 100.006.014 EC Number KEGG RTECS number UNII UN number 1570 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
Y Key: RRKTZKIUPZVBMF-IBTVXLQLSA-N
Y 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
Properties C 23 H 26 N 2 O 4 Molar mass −1 Melting point 178 °C (352 °F; 451 K) Hazards GHS labellingDanger 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 their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Brucine is analkaloid closely related tostrychnine , most commonly found in theStrychnos nux-vomica toxic than brucine. Inchemical synthesis , it can be used as a tool forstereospecific chemical syntheses .
Brucine's name derives from this of the genusBrucea James Bruce who brought backBrucea antidysenterica from Ethiopia.
Brucine was discovered in 1819 by the French chemistPelletier and the French pharmacistCaventou in thebark of theStrychnos nux-vomica tree.[ 1] chemical 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]
Brucine can be detected and quantified usingliquid chromatography-mass spectrometry .[ 3] chromic acid .[ 4]
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] stationary phase inHPLC to selectively bind one of two anionic enantiomers.[ 6] fractional crystallization inacetone to resolve dihydroxyfatty acids ,[ 7] aryl carbinols .[ 8] potassium 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] breast cancer ,[ 11] therapeutic window has limited its use as a treatment forcancer .
Brucine is also used intraditional Chinese medicine as ananti-inflammatory andanalgesic agent,[ 12] Ayurveda andhomeopathy drugs.[ 13]
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 Alexandre 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 [ 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.
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] LD50 varies considerably.
Brucine's mechanism of action ^ 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 ^ Buckingham, J (2007).Bitter Nemesis: The Intimate History of Strychnine . CRC Press. p. 225. ^ 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 . ^ Glasby, J. (1975).Encyclopedia of the alkaloids ISBN 9780306308451 ^ Koskinen, A (1993).Asymmetric synthesis of natural products 17 ,28– 29. ^ 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 . ^ 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 . ^ 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 . ^ 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 . ^ 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 . ^ 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 . ^ 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 . ^ 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 . ^ "List of denaturants authorized for denatured spirits" .www.law.cornell.edu . Cornell Law School. 30 August 2016. Retrieved2019-08-24 .^ Dumas, Alexandre (1845).The Count of Monte Cristo . Feedbooks. p. 622. ^ "Synopsis for The Mechanic" .IMDb . Retrieved30 April 2015 .^ Gosselin, R. E.; Smith, R. P.; Hodge, H. C. (1984).Clinical Toxicology of Commercial Products (5 ed.). Baltimore/London: Williams & Wilkins. ^ "Brucine" .Toxnet . NIH. Retrieved2018-10-07 .
Receptor (ligands )
GlyR Tooltip Glycine receptor Positive modulators: Alcohols (e.g.,brometone ,chlorobutanol (chloretone) ,ethanol (alcohol) ,tert -butanol (2M2P)tribromoethanol ,trichloroethanol ,trifluoroethanol )Alkylbenzene sulfonate Anandamide Barbiturates (e.g.,pentobarbital ,sodium thiopental )Chlormethiazole D12-116 Dihydropyridines (e.g.,nicardipine )Etomidate Ginseng constituents (e.g.,ginsenosides (e.g.,ginsenoside-Rf ))Glutamic acid (glutamate) Ivermectin Ketamine Neuroactive steroids (e.g.,alfaxolone ,pregnenolone (eltanolone) ,pregnenolone acetate ,minaxolone ,ORG-20599 )Nitrous oxide Penicillin G Propofol Tamoxifen Tetrahydrocannabinol Triclofos Tropeines (e.g.,atropine ,bemesetron ,cocaine ,LY-278584 ,tropisetron ,zatosetron )Volatiles /gases (e.g.,chloral hydrate ,chloroform ,desflurane ,diethyl ether (ether) ,enflurane ,halothane ,isoflurane ,methoxyflurane ,sevoflurane ,toluene ,trichloroethane (methyl chloroform) ,trichloroethylene )Xenon Zinc Antagonists: 2-Aminostrychnine 2-Nitrostrychnine 4-Phenyl-4-formyl-N-methylpiperidine αEMBTL Bicuculline Brucine Cacotheline Caffeine Colchicine Colubrine Cyanotriphenylborate Dendrobine Diaboline Endocannabinoids (e.g.,2-AG ,anandamide (AEA) )Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline N-Methylstrychnine N,N-Dimethylmuscimol Nipecotic acid Pitrazepin Pseudostrychnine Quinolines (e.g.,4-hydroxyquinoline ,4-hydroxyquinoline-3-carboxylic acid ,5,7-CIQA ,7-CIQ ,7-TFQ ,7-TFQA )RU-5135 Sinomenine Strychnine Thiocolchicoside Tutin Negative modulators: Amiloride Benzodiazepines (e.g.,bromazepam ,clonazepam ,diazepam ,flunitrazepam ,flurazepam )Corymine Cyanotriphenylborate Daidzein Dihydropyridines (e.g.,nicardipine ,nifedipine ,nitrendipine )Furosemide Genistein Ginkgo constituents (e.g.,bilobalide ,ginkgolides (e.g.,ginkgolide A ,ginkgolide B ,ginkgolide C ,ginkgolide J ,ginkgolide M ))Imipramine NBQX Neuroactive steroids (e.g.,3α-androsterone sulfate ,3β-androsterone sulfate ,deoxycorticosterone ,DHEA sulfate ,pregnenolone sulfate ,progesterone )Opioids (e.g.,codeine ,dextromethorphan ,dextrorphan ,levomethadone ,levorphanol ,morphine ,oripavine ,pethidine ,thebaine )Picrotoxin (i.e.,picrotin andpicrotoxinin )PMBA Riluzole Tropeines (e.g.,bemesetron ,LY-278584 ,tropisetron ,zatosetron )Verapamil Zinc NMDAR Tooltip N-Methyl-D-aspartate receptor
Transporter (blockers )
GlyT1 Tooltip Glycine transporter 1 GlyT2 Tooltip Glycine transporter 2
