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Brucine information


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
CAS Number
  • 357-57-3 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:3193
ChEMBL
  • ChEMBL501756 checkY
ChemSpider
  • 390579 checkY
ECHA InfoCard 100.006.014 Edit this at Wikidata
EC Number
  • 206-614-7
IUPHAR/BPS
  • 342
KEGG
  • C09084 checkY
PubChem CID
  • 442021
RTECS number
  • EH8925000
UNII
  • 6NG17YCK6H checkY
UN number 1570
CompTox Dashboard (EPA)
  • DTXSID2024662 Edit this at Wikidata
InChI
  • 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
SMILES
  • 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
Chemical formula
C23H26N2O4
Molar mass 394.471 g·mol−1
Melting point 178 °C (352 °F; 451 K)
Hazards
GHS labelling:
Pictograms
GHS06: Toxic
Signal word
Danger
Hazard statements
H300, H330, H412
Precautionary statements
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).
checkY verify (what is checkY☒N ?)
Infobox references

Brucine, is an alkaloid closely related to strychnine, most commonly found in the Strychnos nux-vomica tree. Brucine poisoning is rare, since it is usually ingested with strychnine, and strychnine is more toxic than brucine. In synthetic chemistry, it can be used as a tool for stereospecific chemical syntheses.

Brucine is named from the genus Brucea, named after James Bruce who brought back Brucea antidysenterica from Ethiopia.

and 26 Related for: Brucine information

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Brucine

Last Update:

Brucine, is an alkaloid closely related to strychnine, most commonly found in the Strychnos nux-vomica tree. Brucine poisoning is rare, since it is usually...

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Jane Stanford

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adult can be as little as 30 mg). The water also contained the alkaloid brucine and other substances, suggesting that the source was a rodent poison derived...

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Strychnine

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plants a 9,10-dimethoxy derivative of strychnine, the alkaloid brucine, is also present. Brucine is not as poisonous as strychnine. Historic records indicate...

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Strychnos alkaloids

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contain up to 2.5% strychnine and brucine. The primary representative of this group of alkaloids are strychnine and brucine. Other notable representatives...

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Strychnos ignatii

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Ignatius' beans. The beans of the plant contain the alkaloids strychnine and brucine. Ignatia. enotes.com Archived March 4, 2011, at the Wayback Machine Datta...

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Fish

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Vomitoxin Zeranol Zearalenone Plant toxins Amygdalin Anisatin Antiarin Brucine Chaconine Cicutoxin Coniine Daphnin Delphinine Divicine Djenkolic acid...

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Enantioselective synthesis

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most often attributed to Willy Marckwald, Universität zu Berlin, for a brucine-catalyzed enantioselective decarboxylation of 2-ethyl-2-methylmalonic acid...

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Cacotheline

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chemical formula C21H21N3O7. It is a nitro derivative of brucine obtained by reaction of brucine with nitric acid. It is used as an indicator in the titrimetric...

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Bitterant

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variety of applications as an aversive agent. Sucrose octaacetate Quercetin Brucine Quassin The threshold for stimulation of bitter taste by quinine averages...

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Dextromethorphan

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N-methylation. In this example, the purification was done by formation of a brucine salt.[citation needed] This process has also been patented by Roche. The...

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Phthalic anhydride

Last Update:

resolvable because they form diastereomeric salts with chiral amines such as brucine. A related ring-opening reaction involves peroxides to give the useful...

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Indole alkaloid

Last Update:

monoterpenoid fragment C9 C10 Corynanthe Ajmaline, aquamycin, strychnine, brucine Ajmalicine, yohimbine, reserpine, sarpagin, mitragynine Iboga Ibogaine...

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Toluene

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2-Nitrostrychnine 4-Phenyl-4-formyl-N-methylpiperidine αEMBTL Bicuculline Brucine Cacotheline Caffeine Colchicine Colubrine Cyanotriphenylborate Dendrobine...

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Tetrahydrocannabinol

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2-Nitrostrychnine 4-Phenyl-4-formyl-N-methylpiperidine αEMBTL Bicuculline Brucine Cacotheline Caffeine Colchicine Colubrine Cyanotriphenylborate Dendrobine...

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Alkaloid

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Strychnine tree. Its seeds are rich in strychnine and brucine....

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Pentobarbital

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2-Nitrostrychnine 4-Phenyl-4-formyl-N-methylpiperidine αEMBTL Bicuculline Brucine Cacotheline Caffeine Colchicine Colubrine Cyanotriphenylborate Dendrobine...

Word Count : 1924

Nitrous oxide

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2-Nitrostrychnine 4-Phenyl-4-formyl-N-methylpiperidine αEMBTL Bicuculline Brucine Cacotheline Caffeine Colchicine Colubrine Cyanotriphenylborate Dendrobine...

Word Count : 10073

Taurine

Last Update:

2-Nitrostrychnine 4-Phenyl-4-formyl-N-methylpiperidine αEMBTL Bicuculline Brucine Cacotheline Caffeine Colchicine Colubrine Cyanotriphenylborate Dendrobine...

Word Count : 2875

List of biomolecules

Last Update:

Bicuculline Bilirubin Biopolymer Biotin (Vitamin H) Brefeldin A Brassinolide Brucine Butyric acid Cadaverine Caffeine Calciferol (Vitamin D) Calcitonin Calmodulin...

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Flunitrazepam

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2-Nitrostrychnine 4-Phenyl-4-formyl-N-methylpiperidine αEMBTL Bicuculline Brucine Cacotheline Caffeine Colchicine Colubrine Cyanotriphenylborate Dendrobine...

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Chiral resolution

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Examples of chiral derivatizing agents are tartaric acid and the amine brucine. The method was introduced (again) by Louis Pasteur in 1853 by resolving...

Word Count : 896

Botulinum toxin

Last Update:

Vomitoxin Zeranol Zearalenone Plant toxins Amygdalin Anisatin Antiarin Brucine Chaconine Cicutoxin Coniine Daphnin Delphinine Divicine Djenkolic acid...

Word Count : 11725

Chloroform

Last Update:

2-Nitrostrychnine 4-Phenyl-4-formyl-N-methylpiperidine αEMBTL Bicuculline Brucine Cacotheline Caffeine Colchicine Colubrine Cyanotriphenylborate Dendrobine...

Word Count : 5618

Furosemide

Last Update:

2-Nitrostrychnine 4-Phenyl-4-formyl-N-methylpiperidine αEMBTL Bicuculline Brucine Cacotheline Caffeine Colchicine Colubrine Cyanotriphenylborate Dendrobine...

Word Count : 3648

Xenon

Last Update:

2-Nitrostrychnine 4-Phenyl-4-formyl-N-methylpiperidine αEMBTL Bicuculline Brucine Cacotheline Caffeine Colchicine Colubrine Cyanotriphenylborate Dendrobine...

Word Count : 11995

Colchicine

Last Update:

2-Nitrostrychnine 4-Phenyl-4-formyl-N-methylpiperidine αEMBTL Bicuculline Brucine Cacotheline Caffeine Colchicine Colubrine Cyanotriphenylborate Dendrobine...

Word Count : 5673

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