Grundinformationen
- Standard-SMILES
COc1cc2c(cc1OC)[C@@]13CCN4CC5=CCO[C@H]6CC(=O)N2[C@H]1[C@H]6[C@H]5C[C@H]43- InChIKey
RRKTZKIUPZVBMF-IBTVXLQLSA-N- Summenformel
- C23H26N2O4
- Durchschnittliche Molmasse
- 394,5 g/mol
- Monoisotopische Masse
- 394,18925731
Überblick
Brucine appears as a white crystalline solid. Combustible but may require some effort to ignite. Toxic by inhalation (vapor, dust, etc.) and ingestion.
Namen und Bezeichner
- Bevorzugter Name
- Brucine
- IUPAC
- (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]quinolin-14-one
Namen und Synonyme
Weitere Namen anzeigen
Datenbank-Bezeichner
- CAS
357-57-3- PubChem CID
- 442021
- DTXSID
DTXSID2024662- ChEMBL
CHEMBL501756- ChEBI
CHEBI:3193- UNII
- 6NG17YCK6H
- EC Number
- 206-614-7
- Nikkaji
- J5.693F
Eigenschaften
Berechnete Struktureigenschaften
- XLogP
- 1
- Polarare Oberfläche (TPSA)
- 51,2 Ų
- H-Brücken-Donoren
- 0
- H-Brücken-Akzeptoren
- 5
- Frei drehbare Bindungen
- 2
- Schwere Atome
- 29
- Formalladung
- 0
- Komplexität
- 785
Experimentelle und physikochemische Eigenschaften
LogP
Log Kow= 0.98
0.98
Color/Form
Needles from acetone + water
COLORLESS CRYSTAL OR WHITE, CRYSTALLINE POWDER
White, crystalline alkaloid
Colorless prisms (from ethanol/water)
Solubility
Crystals. Sol in water or alcohol. The solns are neutral or slightly acid. /Hydrochloride/
Prisms, dec 230 °C. Sol in water or alcohol. /Nitrate dihydrate/
Slightly soluble in ethyl ether and benzene; very soluble in ethanol.
Slightly sol in water, ether, glycerin and ethyl acetate.
Soluble in alcohol, chloroform, and benzene; slightly soluble in ether, glycerol, and ethyl acetate.
In water, 3.2X10+3 mg/l @ 15 °C
Boiling Point
470 °C
470 °C
470 °C @760 [mm Hg]
Melting Point
352 °F (NTP, 1992)
178 °C
178 °C
178 °C
Sicherheit und Regulatorisches
GHS-Klassifizierung
GHS Classification
Danger
H300: Fatal if swallowed [Danger Acute toxicity, oral]
P260, P264, P270, P271, P273, P284, P301+P316, P304+P340, P316, P320, P321, P330, P403+P233, P405, and P501 (click each P-code to see the statement)
Danger
H300+H330 (32.9%): Fatal if swallowed or if inhaled [Danger Acute toxicity, oral; acute toxicity, inhalation]
P260, P264, P270, P271, P273, P284, P301+P316, P304+P340, P316, P320, P321, P330, P403+P233, P405, and P501 (click each P-code to see the statement)
Gefahrenhinweise
Regulatory Information
Chemical: Strychnidin-10-one, 2,3-dimethoxy-
Strychnidin-10-one, 2,3-dimethoxy-, (brucine): HSNO Approval: HSR001529 Approved with controls
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Fire Hazards
Special Hazards of Combustion Products: Toxic oxides of nitrogen may form in fires. (USCG, 1999)
· Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes.
Combustible. Gives off irritating or toxic fumes (or gases) in a fire.
Health Hazards
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. (USCG, 1999)
· Highly toxic, may be fatal if inhaled, ingested or absorbed through skin.
RCRA Requirements
P018; As stipulated in 40 CFR 261.33, when brucine, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).
Sicherheit und Schutzausrüstung
Fire Fighting
Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
Use water spray, powder, foam, carbon dioxide.
First Aid Measures
Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.
Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .
First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.
Rinse mouth. Give a slurry of activated charcoal in water to drink. Refer for medical attention . Avoid unnecessary stimulation of the victim.
Accidental Release Measures
· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.
· Do not touch damaged containers or spilled material unless wearing appropriate protective clothing.
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
General First Aid:
Fire Fighting Procedures
Wear goggles and self-contained breathing apparatus /while fighting fires/. Extinguish with water, dry chemical, foam, or carbon dioxide.
If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire (material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use foam, dry chemical, carbon dioxide.
Cleanup Methods
1. Ventilate area of spill. 2. Collect spilled material in the most convenient and safe manner and deposit in sealed containers for reclamation, or for disposal in a secured sanitary landfill. Liquid containing strychnine should be absorbed in vermiculite, dry sand, earth, or a similar material. /Strychnine/
Pour into sodium bicarbonate or a mixture of sand-soda ash (9:1). After mixing, transfer into a paper carton filled with packing paper. Burn in an open furnace, or more efficiently in the furnace with afterburner and scrubber.
Environmental considerations - Land spill. Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water. /Strychnine/
Environmental considerations - Water spill; Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. If dissolved, in region of 10 ppm or greater concn, apply activated carbon at ten times the spilled amount. Remove trapped material with suction hoses. Use mechanical dredges or lifts to remove immobilized masses of pollutants and precipitates. /Strychnine/
Spread over with 9:1 mixture of sand and soda ash. After mixing, transfer into a paper carton, stuffed with ruffled paper. Burn in an open furnace with the utmost care or in the furnace with afterburner and scrubber.
Disposal Methods
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number P018, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.
(a) Dissolve in such combustible solvent as alcohols, benzene, etc. Spray the solution into the furnace with afterburner and scrubber. (b) Pour into sodium bicarbonate or a mixture of sand-soda ash (9:1). After mixing, transfer into a paper carton filled with packing paper. Burn in an open furnace, or more efficiently in the furnace with afterburner and scrubber.
A good candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A good candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids. /From table/
Spillage Disposal
Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.
Toxikologische Informationen
Treatment
Treatment of brucine poisoning involves an oral application of an activated charcoal infusion to absorb any poison within the digestive tract that has not yet been absorbed into the blood. Anticonvulsants such as phenobarbital or diazepam are administered to control convulsions, along with muscle relaxants such as dantrolene to combat muscle rigidity. (L1228)
Ecotoxicity Values
LC50 Lepomis macrochirus (bluegill sunfish) 36 ppm/96 hr (static bioassay in fresh water @ 23 °C, with mild aeration after 24 hr)
LC50 Menidia beryllina 20 ppm/96 hr (static bioassay in synthetic seawater @ 23 °C, with mild aeration after 24 hr)
Environmental Fate
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 81(SRC), determined from a structure estimation method(2), indicates that brucine is expected to have high mobility in soil(SRC). However, the ability of brucine to adsorb to sediments and soil can not be predicted with certainty since this compound may act markedly different than its estimated Koc value indicates(SRC). Volatilization of brucine from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 2.1X10-16 atm-cu m/mole(SRC) using a fragment constant estimation method(3). Brucine is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.0X10-10 mm Hg(SRC), determined from a fragment constant method(4). Half-life data for brucine indicate that biodegradation in soil may occur(SRC).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 81(SRC), determined from a structure estimation method(2), indicates that brucine is not expected to adsorb to suspended solids and sediment in water(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 2.1X10-16 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). A pKa of 8.28 indicates brucine will exist almost entirely in the ionized form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process. According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(6) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low.
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), brucine, which has an estimated vapor pressure of 1.0X10-10 mm Hg at 25 °C(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase brucine may be removed from the air by direct photolysis and dry deposition(SRC).
Exposure Routes
The substance can be absorbed into the body by inhalation of its aerosol and by ingestion.
Oral (ingestion) (L1817) ; dermal (L1817)
Toxicity Summary
The CIR Expert Panel concluded that the available data are insufficient to support the safety of Alcohol Denat., SD Alcohol 39, and SD Alcohol 40 denatured with Quassin, Brucine, and Brucine Sulfate in cosmetic products, and that the available data are insufficient to support the safety of Quassin, Brucine, and Brucine Sulfate as denaturants.
Ingredients for which the data are insufficient and their use in cosmetics is not supported
Brucine acts as an antagonist at the inhibitory or strychnine-sensitive glycine receptor, a ligand-gated chloride channel in the spinal cord and the brain. (L1230)
Signs and Symptoms
See Ingestion.
Redness.
Headache. Nausea. Vomiting. Muscle twitching. Restlessness. Convulsions. Laboured breathing.
Brucine causes muscular convulsions of increasing intensity and frequency and eventually death through asphyxia or sheer exhaustion. (L1227)
Medical Surveillance
1) Initial Medical Screening: Employees should be screened for history of certain medical conditions ... which might place the employee at incr risk from strychnine exposure. ... Persons with a history of convulsive disorders may be more susceptible to the effects of this agent. 2) Periodic Medical Examination: Any employee developing ... /convulsive disorders/ should be referred for further medical examination. /Strychnine/
Soil Adsorption/Mobility
Using a structure estimation method based on molecular connectivity indices(1), the Koc for brucine can be estimated to be 81(SRC). According to a classification scheme(2), this estimated Koc value suggests that brucine is expected to have high mobility in soil. The pKa of brucine is 8.28(3) indicating that this compound will exist in the protonated form in the environment and cations generally adsorb to organic carbon and clay more strongly than their neutral counterparts. Volatilization from moist soil surfaces is not expected to be an important fate process because the cation is not expected to volatilize. Therefore, the ability of brucine to adsorb to sediments an soil cannot be predicted with certainty since this compound may act markedly different than its estimated Koc value indicates(SRC).
Regulatorische Informationen
RCRA Requirements
P018; As stipulated in 40 CFR 261.33, when brucine, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to federal and/or state hazardous waste regulations. Also defined as a hazardous waste is any container or inner liner used to hold this waste or any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5(e)).
TSCA Requirements
Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Brucine is included on this list.
CERCLA Reportable Quantities
Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).
Chemie und Industrie
Pharmakologische Informationen
MeSH Pharmacological Classification
Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity.
Compounds capable of relieving pain without the loss of CONSCIOUSNESS.
Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)
Verwendung und Herstellung
Uses
CIR ingredient: Brucine
Extracted from the seeds and bark of Strychnos aculeata; Used for denaturing alcohol and oils; Also used as an additive to lubricants, a rodent poison, a CNS stimulant, and a chemical reagent; [HSDB] A poison resembling strychnine that is much less potent; [Reference #1]
Farming (Pesticides) [Category: Industry]
DENATURANT FOR ETHANOL; REAGENT FOR SEPARATING RACEMIC MIXTURES.
Rodent poison.
THE MOST COMMON DENATURANT /FOR ETHANOL/ USED NOW ... IN COSMETIC PREPARATIONS ...
U.S. Imports
(1972) 2.12X10+7 GRAMS (BRUCINE & CMPDS)
(1975) 1.20X10+7 GRAMS (BRUCINE & CMPDS)
(1984) 2.84X10+8 g
Methods of Manufacturing
EXTRACTED FROM THE SEEDS & BARK OF STRYCHNOS ACULEATA.
By extraction & subsequent crystallization from nux vomica or ignatia seeds.
From Strychnos seeds (Strychnos nux-vomica L. and S. igantti Berg., Loganiaceae).
Prepn from strychnine, q.v.: E. Tedeschi et al., Tetrahedron 24, 4573 (1968); P. Rosenmund et al., Ber. 101, 2754 (1968).
Formulations/Preparations
Forms brucine sulfate, hydrochloride, & nitrate (mp 230 °C).
THE MOST COMMON DENATURANT /FOR ETHANOL/ USED NOW ... IN COSMETIC PREPARATIONS, IS SD-40 WHICH HAS THE FOLLOWING FORMULATIONS: 3 OZ OF BRUCINE (ALKALOID) OR BRUCINE SULFATE
Alkaloid, NF grade; dihydrate, white powder grade; sulfate, NF grade
Available as the free base or as the sulfate salt.
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