ChemicalBook >> CAS DataBase List >>10,11-Dimethoxystrychnine

10,11-Dimethoxystrychnine

CAS No.
357-57-3
Chemical Name:
10,11-Dimethoxystrychnine
Synonyms
Brucin;Brucina;BRUCINE;BrucineGr;l-Brucine;BrucineA.R.;(-)-BRUCINE;Brucine CRS;Brucine AR 25GM;BRUCINE ALKALOID
CBNumber:
CB1208445
Molecular Formula:
C23H26N2O4
Formula Weight:
394.46
MOL File:
357-57-3.mol

10,11-Dimethoxystrychnine Properties

Melting point
175-178 °C (dec.)(lit.)
alpha
-118 º (c=2.5 in chloroform)
Boiling point
518.67°C (rough estimate)
Density
1.2119 (rough estimate)
refractive index
1.6300 (estimate)
storage temp.
Store at RT
pka
8.28(at 25℃)
form
Powder
color
White to light beige
Water Solubility
Soluble in alcohol, chloroform, and benzene, slightly soluble in water, ether, and glycerol
Merck
14,1455
Stability
Stable. Combustible. Incompatible with strong oxidizing agents.
CAS DataBase Reference
357-57-3(CAS DataBase Reference)
EWG's Food Scores
2-3
FDA UNII
6NG17YCK6H
NIST Chemistry Reference
Brucine(357-57-3)
EPA Substance Registry System
Brucine (357-57-3)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS06
Hazard statements  H300-H330-H412
Precautionary statements  P301+P310a-P304+P340-P320-P330-P405-P501a
Hazard Codes  T+
Risk Statements  26/28-52/53
Safety Statements  13-45-61
RIDADR  UN 1570 6.1/PG 1
WGK Germany  3
RTECS  EH8925000
TSCA  Yes
HazardClass  6.1(a)
PackingGroup  I
HS Code  29399900

10,11-Dimethoxystrychnine price More Price(22)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 399027 Brucine anhydrous, 98% 357-57-3 5G $43.3 2022-05-15 Buy
Sigma-Aldrich 399027 Brucine anhydrous, 98% 357-57-3 25G $118 2022-05-15 Buy
Sigma-Aldrich 8.18308 (-)-Brucine for resolution of racemates for synthesis 357-57-3 50 g $125.8 2021-12-16 Buy
Alfa Aesar J61178 Brucine 357-57-3 25g $76 2022-04-27 Buy
Alfa Aesar J61178 Brucine 357-57-3 100g $230 2022-04-27 Buy
Product number Packaging Price Buy
399027 5G $43.3 Buy
399027 25G $118 Buy
8.18308 50 g $125.8 Buy
J61178 25g $76 Buy
J61178 100g $230 Buy

10,11-Dimethoxystrychnine Chemical Properties,Uses,Production

Description

As a Chinese medicine, brucine was firstly recorded in Compendium of Materia Medica. The Chinese name for brucine is “Maqian” because it looks like ancient coins with horse icon, where “Ma” refers to “horse” and “qian” refers to “coins.” This traditional Chinese herb has cold, bitter, and toxic properties. It can be used to treat typhoid fever, throat pain, and lumps. Brucine is mainly extracted from the traditional Chinese medicine “Maqian.” In 1819, Pelletier and Caventou firstly isolated the alkaline brucine from the seeds and bark of Strychnos nux-vomica L.?Brucine is the dry and mature seeds of Loganiaceae Evergreen tree plants including Strychnos nux-vomica L. and Strychnos pierriana A.W. Hill.

Chemical Properties

White powder

Physical properties

Appearance: white crystalline powder; tastes very bitter. Solubility: slightly soluble in water; soluble in ether, chloroform, ethanol, methanol, and other organic solvents . Melting point: 175–178?°C. Specific optical rotation: ?118°.

Uses

Brucine is used as a denaturing alcohol, lubricant additive, separation of racemic mixtures. Proposed to reduce inflammatory mediators including COX-2, PGE2 and thromboxane B2. Able to induce cell apoptosis, with cytotoxic and antiproliferative effects.

Uses

Brucine occurs in the seeds of strychnosspecies (Strychnos nux vomica L. and otherspecies). It is used for denaturing alcoholsand oils; for separating racemic mixtures;and as an additive to lubricants. It is alsoused for colorimetric analysis of nitrate.Therapeutically, it is used as a stimulant.

Uses

10,11-Dimethoxystrychnine can be used for antineoplastic, convulsant.

General Description

A white crystalline solid. Combustible but may require some effort to ignite. Toxic by inhalation (vapor, dust, etc.) and ingestion.

Air & Water Reactions

Slightly soluble in water.

Hazard

Poison by ingestion and inhalation.

Health Hazard

The toxicity of brucine is similar to that ofstrychnine. It is a very poisonous alkaloid. Itis a strong convulsant; excites all portions ofthe central nervous system. Toxic symptomsinclude headache, tremor, muscular rigidity,and convulsions. Death may occur fromrespiratory arrest after a few convulsions.
LD50 value, subcutaneous (mice): 60 mg/kg.

Health Hazard

Chemical is toxic if inhaled, swallowed, or absorbed through skin. Inhalation produces intense bitter taste. Ingestion causes nausea, vomiting, restlessness, excitement, twitching, and (rarely) convulsions. Contact with dust irritates eyes.

Fire Hazard

Special Hazards of Combustion Products: Toxic oxides of nitrogen may form in fires.

Agricultural Uses

Rodenticide: Used in the manufacture of other chemicals, in perfumes, as a medication for animals, and as a poison for rodents

Trade name

DOLCO MOUSE CEREAL®; PIED PIPER MOUSE SEED® (Brucine)

Pharmacology

1. Analgesic effects: Brucine is reported to exert analgesic effects through both central and peripheral pathways. Possible mechanisms of the analgesic effects include blocking the voltage-gated sodium channel, inhibiting the synthesis of PGE2, acting on the adrenergic receptor and the L-arginine-NO pathway. Brucine (0.48?mg/kg) can significantly elevate the pain threshold in mice.
2. Anti-tumor effects: Studies have shown that brucine inhibits the cell proliferation in breast cancer, liver cancer, leukemia, and Ehrlich ascites tumors by inducing tumor cell apoptosis, inhibiting angiogenesis, reversing tumor multidrug resistance, and regulating the expression of various cytokines. In addition, at the dose of 320?μg/ml, the in?vitro hepatocarcinoma cell growth inhibition rate of brucine is nearly 100%.
3. Anti-pathogen effects: In vitro study shows that 0.1% brucine can completely inhibit the growth of Haemophilus influenzae, Streptococcus pneumoniae, and alpha Streptococcus and Mlicrococcus catarrhalis. At the dose of 500?μg/ml, the inhibitory rate of brucine on human immunodeficiency virus reverse transcriptase is above 30%.
4. Other pharmacological effects: Anti-inflammation, regulation of the immune system, regulation of the cardiovascular system, antitussive, expectorant, and antiasthenic and antibacterial effects.

Clinical Use

The applications of brucine include reducing swelling; resolving mass; activating meridians to stop pain; attenuating rheumatism, stubborn paralysis, and numbness paralysis; alleviating bruises; etc. It has been used for nearly a thousand years and achieved prominent clinical efficacy. In the clinical practice, brucine is used as a compatibility prescription or compound medicine in treating rheumatism, rheumatoid arthritis, stroke hemiplegia, dementia, retinopathy, and orthopedic and other surgical diseases.
Brucine is the main active ingredient in Strychnos and plays an important role in treating diseases. However, brucine is also a toxic ingredient, which limits the scope of its clinical application. Further studies of its pharmacological effects and toxicity will improve its clinical application.

Safety Profile

A poison by subcutaneous, intravenous, and intraperitoneal routes. An alkaloid-like strychnine, but one-sixth as toxic. When heated to decomposition it emits toxic fumes of Nx,. See also STRYCHNINE

Purification Methods

Crystallise brucine once from water or aqueous Me2CO (as the tetrahydrate), then suspend it in CHCl3 and shake with anhydrous Na2SO4 (to dehydrate the brucine, which then dissolves). Precipitate it by pouring the solution into a large bulk of dry pet ether (b 40-60o), filter and heat to 120o in a high vacuum [Turner J Chem Soc 842 1951]. The tetrahydrate crystallises from a mixture of EtOH and H2O as colourless elongated needles [Eeles Acta Cryst 6 809 1953, Beilstein 27 III/IV 7875.] VERY POISONOUS

17301-81-4
357-57-3
Synthesis of 10,11-Dimethoxystrychnine from brucine N-oxide hydrate

10,11-Dimethoxystrychnine Preparation Products And Raw materials

STRYCHNIDIN-10-ONE,2,3-DIMETHOXY 10,11-Dimethystrychnine 10,11-DIMETHOXYSTRYCHNINE BRUCINE, MICROREAGENT FOR THE DETERMINAT ION OF NITRATE BRUCINE FREE BASE BRUCINE:STRYCHNIDIN-10-ONE,2,3-DIMETHOXY BrucineA.R. BrucineGr BrucineAnhydrous99% 2,3-DIMETHOXYSTRYCHNIDIN-10-ONE Strychidin-10-one,2,3-dimethoxy- BRUCINE ALKALOID/BASE/DIHYDRATE/SALT/SULPHATE 2,3-Dimethoxystrychinidin-10-one RCRA waste number PO-18 Brucine,99%,anhydrous Brucine, synthesis grade Brucine: (2,3-Dimethoxysrychnine) brucine 2,3-dimethoxystrychnine l-Brucine (4aR,4a1R,5aS,8aR,8a1S,15aS)-10,11-diMethoxy-4a1,5,5a,7,8,8a1,15,15a-octahydro-2H-4,6-Methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinolin-14(4aH)-one 2,3-Dimethoxystrychnidin-10-one 10,11-Dimethoxystrychnine (-)-BRUCINE FOR RESOLUTION OF RACEMATES BRUCINE GR FOR ANALYSIS 10 G BRUCINE GR FOR ANALYSIS 50 G 2,3-dimethoxy-strychnidin-10-on 2,3-Dimethoxystrychnidine-10-one 2,3-dimethoxy-strychnin 2,3-Dimethoxy-strychnine Brucin Brucina brucine,anhydrous Dimethoxy strychnine dimethoxystrychnine Rcra waste number P018 rcrawastenumberp018 Strychnine, 2,3-dimethoxy- (-)-BRUCINE BRUCINE BRUCINE ALKALOID BRUCINE TETRAHYDRATE (4aR,5aS,8aR,13aS,15aS,15bR)-10,11-dimethoxy-4a,5,5a,7,8,13a,15,15a,15b,16-decahydro-2H-4,6-methanoindolo[3,2,1-ij]oxepino[2,3,4-de]pyrrolo[2,3-h]quinoline-14-one Brucine CRS Brucine AR 25GM Brucine, GR 99%+ 357-57-3 C23H26N2O4 Optical Resolution Alkaloids for Resolution of Acids Indole Alkaloids Chiral Resolution Reagents Asymmetric Synthesis Chiral Resolving Reagents chemical reagent pharmaceutical intermediate phytochemical reference standards from Chinese medicinal herbs (TCM). standardized herbal extract