Brucine

HCID 442021CAS 357-57-3

기본 정보

표준 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
분자식
C23H26N2O4
평균 분자량
394.5 g/mol
단동위원소 질량
394.18925731

개요

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

이름 및 식별자

우선 이름
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

이름 및 동의어

BRUCINE357-57-310,11-DimethoxystrychnineBrucinum2,3-Dimethoxystrychnine(-)-Brucine2,3-Dimethoxystrychnidin-10-oneBruzinl-BrucineBrucine alkaloidStrychnidin-10-one, 2,3-dimethoxy-10,11-Dimethystrychnine
이름 더 보기
DTXSID2024662Brucina2,3-Dimethoxy-strychnine6NG17YCK6HStrychnine, 2,3-dimethoxy-Dimethoxy strychnineNSC-757797DTXCID204662

데이터베이스 식별자

CAS
357-57-3
PubChem CID
442021
DTXSID
DTXSID2024662
ChEMBL
CHEMBL501756
ChEBI
CHEBI:3193
UNII
6NG17YCK6H
EC Number
206-614-7
Nikkaji
J5.693F

물성

구조 계산 물성

XLogP
1
극성 표면적
51.2 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
5
회전 가능 결합 수
2
무거운 원자 수
29

실험 및 물리화학적 성질

Chemical ClassesBiological Agents -> Plant Toxins
DrugsDEA NFLIS-Drug Category -> Stimulants
CosmeticsCosmetic ingredients (Brucine) -> CIR (Cosmetic Ingredient Review)
LogP · 2건

Log Kow= 0.98

0.98

OdorOdorless
TasteVery bitter taste

안전 및 규제

GHS 분류

GHS Classification · 6건

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)

유해성 정보

Regulatory Information · 3건

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.)

Other Safety InformationIMAP assessments - Brucine: Human health tier II assessment
DOT LabelPoison
Fire Hazards · 3건

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.

Fire PotentialIt is combustible though it may require some effort to ignite.
Health Hazards · 2건

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.

안전 및 보호

Fire Fighting · 2건

Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:

Use water spray, powder, foam, carbon dioxide.

First Aid Measures · 4건

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 · 2건

· 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 · 2건

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:

Safe StorageSeparated from strong oxidants and food and feedstuffs. Dry. Well closed.
Exposure Control and Personal Protection· Wear positive pressure self-contained breathing apparatus (SCBA).

독성 정보

Treatment · 1건

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)

Health EffectsDeath may result from asphyxia or sheer exhaustion. (L1227)
Ecotoxicity Values · 2건

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 · 3건

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).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Exposure Routes · 2건

The substance can be absorbed into the body by inhalation of its aerosol and by ingestion.

Oral (ingestion) (L1817) ; dermal (L1817)

규제 정보

RCRA Requirements · 1건

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 · 1건

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 · 1건

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).

화학 및 산업

약리 정보

Metabolism/MetabolitesBRUCINE YIELDS BRUCINE-N-OXIDE IN BACILLUS; YIELDS 2-HYDROXY-3-METHOXYSTRYCHNINE & 3-HYDROXY-2-METHOXYSTRYCHNINE IN RABBITS.
MeSH Pharmacological Classification · 3건

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)

용도 및 제조

Uses · 6건

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 · 3건

(1972) 2.12X10+7 GRAMS (BRUCINE & CMPDS)

(1975) 1.20X10+7 GRAMS (BRUCINE & CMPDS)

(1984) 2.84X10+8 g

Methods of Manufacturing · 4건

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 · 4건

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.

General Manufacturing InformationStrychnidin-10-one, 2,3-dimethoxy-: ACTIVE

관련 반응

31건

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