10,11-Dimethoxystrychnine Chemical 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

solubility 

>15.6mg/mL in DMSO

form 

Powder

pka

8.28(at 25℃)

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.

LogP

0.980

CAS DataBase Reference

357-57-3(CAS DataBase Reference)

NIST Chemistry Reference

Brucine(357-57-3)

EPA Substance Registry System

Brucine (357-57-3)

Safety Information

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

Hazardous Substances Data

357-57-3(Hazardous Substances Data)

MSDS

• Language:English Provider:SigmaAldrich

10,11-Dimethoxystrychnine Usage And Synthesis

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.

Definition

ChEBI: Brucine is a monoterpenoid indole alkaloid and an organic heteroheptacyclic compound.

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

Potential Exposure

Drug, NaturalProduct. Brucine is used as denaturant for Ethanol, alsoresolving agent for isomer separation; in the manufacture ofother chemicals, in perfumes, as a medication for animals,and as a poison for rodents. It is an alkaloid, produced fromstrychnos seeds.

First aid

If this chemical gets into the eyes, remove anycontact lenses at once and irrigate immediately for at least15 min, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts theskin, remove contaminated clothing and wash immediatelywith soap and water. Seek medical attention immediately. Ifthis chemical has been inhaled, remove from exposure,begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR ifheart action has stopped. Transfer promptly to a medicalfacility. When this chemical has been swallowed, get medical attention. Give large quantities of water and inducevomiting. Do not make an unconscious person vomit.

storage

Color Code—Blue: Health Hazard: Store in asecure poison location. Protect against physical damage.Outside or detached storage is preferred. Color Code—Blue: Health Hazard/Poison: Store in a secure poison location. Prior to working with brucine you should be trainedon its proper handling and storage. Store in tightly closedcontainers in a cool, well-ventilated area away from strongoxidizers.

Shipping

Label: “POISONOUS/TOXIC MATERIALS.” Itfalls in Hazard Class 6.1 and Packing Group I.

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

Incompatibilities

Reacts with strong oxidizers. Finely dispersed material in air can cause dust explosions.

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