Brucine

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.

Not to be confused with Brucite.
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 InfoCard 100.006.014
EC Number
  • 206-614-7
KEGG
PubChem CID
RTECS number
  • EH8925000
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
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
C23H26N2O4
Molar mass 394.471 g·mol−1
Melting point 178 °C (352 °F; 451 K)
Hazards
GHS labelling:
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 their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

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

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.