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Home> Encyclopedia >   /  Inorganic Chemicals  /  Organic Intermediates  /  Pharmaceuticals and Biochemicals  /  Pharmaceuticals and Biochemicals  /  Pharmaceuticals and Biochemicals
14252-80-3 structure

bupivacaine hydrochloride

Iupac Name:1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide;hydrochloride
CAS No.:14252-80-3
EINECS(EC#): 241-917-8
Molecular Weight:324.893
Molecular Formula:C18H29ClN2O (isomer)
1. Names and Identifiers
1.1 Synonyms

(+-)-1-butyl-2',6'-pipecoloxylidide monohydrochloride, monohydrate (+-)-Bupivacaine hydrochloride (S)-Bupivacaine hydrochloride 14252-80-3 14252-80-3 (HCl) 15233-43-9 18010-40-7 1-butyl-2-[(2,6-dimethylphenyl)carbamoyl]piperidinium chloride 1-butyl-2-piperidylformo-2',6'-xylidide hydrochloride 1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide 1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide hydrochloride 1-butyl-n-(2,6-dimethylphenyl)-2-piperidinecarboxamide hydrochloride dl-1-n-butylpiperidine-2-carboxylic acid 2,6-dimethylanilide hydrochloride 1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide monohydrochloride 1-butyl-n-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrochloride 1-Butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide--hydrogen chloride (1/1) 2',6'-Pipecoloxylidide, 1-butyl-, hydrochloride 2',6'-pipecoloxylidide, 1-butyl-, monohydrochloride 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, hydrochloride (1:1) 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, monohydrochlorde, monohydrate 2-piperidinecarboxamide, 1-butyl-n-(2,6-dimethylphenyl)-, monohydrochloride 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, monohydrochloride, monohydrate 2-piperidinecarboxamide,1-butyl-n-(2,6-dimethylphenyl)-monohydrochloride,m 2-Piperidinecarboxamide,6-dimethylphenyl)-, hydrochloride 52b803 73360-54-0 (HCl.H2O) AB2000569 ACT04725 AH 2250 ah-2250 AK481431 AKOS015889322 AN-18756 AOB6341 API0001784 AX8018312 B3925 BCP22697 BCP22708 BCP9000461 bicain Bloqueina bupicacain hydrochlorid-1-wasser bupivacain hydrochloride Bupivacaine (hydrochloride) bupivacaine hcl BUPIVACAINE HYDROCHLORIDE bupivacaine hydrochloride (anhydrous) Bupivacaine hydrochloride (Marcain) Bupivacaine hydrochloride [JAN] bupivacaine hydrochloride [usan] Bupivacaine hydrochloride 1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide hydrochloride Bupivacaine hydrochloride anhydrous BUPIVACAINE HYDROCHLORIDE CAS NO.14252-80-3 Bupivacaine hydrochloride kit Bupivacaine hydrochloride preservation free Bupivacaine hydrochloride rs Bupivacaine Hydrochloride, USP bupivacaine monohydrochloride Bupivocoine HCl Carbostesin CCG-39367 CHEBI:31322 CHEBI:77441 CHEMBL1200396 CS-2505 CTK8F8361 dl-1-n-Butylpiperidine-2-carboxylic Acid 2,6-Dimethylanilide Hydrochloride DTXSID0030877 EINECS 241-917-8 FD-0235 FT-0607564 FT-0623287 FT-0658830 FT-0663897 FT-0663899 H875 HE305322 HMS1568N12 HMS1922I12 HY-B0405A IN STOCK BUPIVACAINE HYDROCHLORIDE CAS NO.14252-80-3 J-011502 K-4565 KB-48484 KS-00000M4Q KS-00000XIC lac 43 LAC-43 levobupivacaine hydrochloride (anhydrous) Local Anesthetic Pharmaceutical Raw Material Bupivacaine HCl CAS 14252-80-3 LS-185059 LS-2113 marcain Marcaine hydrochloride preservation free Marcaine Spinal marcainehydrochloride MCULE-5414144502 MLS001361336 MLS002154259 MNarcaine hydrochloride N-(2,6-dimethylphenyl)(1-butyl(2-piperidyl))carboxamide, chloride NCGC00095072-01 NCGC00095072-02 nsc119660 NSC-119660 NSC758631 NSC-758631 Pharmakon1600-01503818 PRESTWICK_894 Q-100158 Q27888209 rac-1-butyl-2-[(2,6-dimethylphenyl)carbamoyl]piperidinium chloride rac-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrochloride s2454 SC-24334 SC-94629 SCHEMBL34374 Sensorcaine SIEYLFHKZGLBNX-UHFFFAOYSA-N sky 0302 SMR000058218 SPECTRUM1503818 SR-05000001874 SR-05000001874-3 ST013772 SW197015-3 Vivacaine Win 11,318 Win 11318 HCl WIN-11318

1.2 Inchi
InChI=1S/C18H28N2O.ClH/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3;/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21);1H
1.3 InChkey
SIEYLFHKZGLBNX-UHFFFAOYSA-N
1.4 Canonical Smiles
CCCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C.Cl
2. Properties
2.1 Appearance
white solid
2.2 Melting Point
249-251 °C
2.3 Boiling Point
423.4 °C at 760 mmHg
2.4 Vapour
2.24E-07mmHg at 25°C
2.5 Flash Point
209.9 °C
2.6 Solubility
soluble
2.7 HS Code
2942000000
2.8 Storage temp
Refrigerator
3. Safety and Handling
3.1 Hazard Codes
T+
3.2 Risk Statements
R26/27/28
3.3 Safety Statements
S22;S36/37/39;S45
3.4 HazardClass
6.1(b)
3.5 Safety

Hazard Codes:?VeryT+
Risk Statements: 26/27/28?
R26/27/28:Very toxic by inhalation, in contact with skin and if swallowed.
Safety Statements: 22-36/37/39-45?
S22:Do not breathe dust.?
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.?
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
RIDADR: UN 2811 6.1/PG 2
WGK Germany: 3
RTECS: TK6125000
HazardClass: 6.1(b)
PackingGroup: III

3.6 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :
TK6125000
CHEMICAL NAME :
2',6'-Pipecoloxylidide, 1-butyl-, hydrochloride, (+-)-
CAS REGISTRY NUMBER :
14252-80-3
LAST UPDATED :
199707
DATA ITEMS CITED :
11
MOLECULAR FORMULA :
C18-H28-N2-O.Cl-H
MOLECULAR WEIGHT :
324.94
WISWESSER LINE NOTATION :
T6NTJ A4 BVMR B1 F1 &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
43 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 200,359,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
6 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 200,359,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
58700 ug/kg
TOXIC EFFECTS :
Behavioral - anticonvulsant Behavioral - somnolence (general depressed activity)
REFERENCE :
AACRAT Anesthesia and Analgesia (New York). (Elsevier Science Pub. Co., Inc., 52 Vanderbilt Ave., New York, NY 10017) V.36- 1957- Volume(issue)/page/year: 60,385,1981
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
59 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 200,359,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
6100 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ANPRBG Anesthesia Progress. (Elsevier Science Publishing Co.,Inc., 655 Avenue of the Americas, New York, NY 10010) V.13- 1966- Volume(issue)/page/year: 36,79,1989
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
22753 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
DDREDK Drug Development Research. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1981- Volume(issue)/page/year: 21,277,1990
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
18 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 200,359,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
3400 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 200,359,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Parenteral
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
48 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 200,359,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intratracheal
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
11 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AIPTAK Archives Internationales de Pharmacodynamie et de Therapie. (Heymans Institute of Pharmacology, De Pintelaan 185, B-9000 Ghent, Belgium) V.4- 1898- Volume(issue)/page/year: 200,359,1972
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
50 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,680,1982
3.7 PackingGroup
III
3.8 Skin, Eye, and Respiratory Irritations
Possible eye, skin, ... and/or respiratory tract irritation. /Bupivacaine hydrochloride/
3.9 Cleanup Methods
Wear approved respiratory protection, chemically compatible gloves, and protective clothing. Wipe up spillage or collect spillage in appropriately labeled container for disposal. Wash spill site. /Bupivacaine hydrochloride/
3.10 Transport
UN 2811
3.11 Fire Fighting Procedures
As with all fires, evacuate personnel to a safe area. Firefighters should use self-contained breathing equipment and protective clothing. /Bupivacaine hydrochloride/
Water spray, dry chemical, carbon dioxide, or foam as appropriate for surrounding fire and materials. /Bupivacaine hydrochloride/
3.12 Fire Potential
This material is assumed to be combustible. /Bupivacaine hydrochloride/
3.13 Formulations/Preparations
Bupivacaine Hydrochloride Preparations Route of Administration Dosage Form Strength Brand or Generic Name (Manufacturer) Parenteral Injection 0.25% Bupivacaine Hydrochloride Injection (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Parenteral Injection 0.25% Marcaine Hydrochloride (Hospira) Parenteral Injection 0.25% Sensorcaine (AstraZeneca) Parenteral Injection 0.5% Bupivacaine Hydrochloride Injection (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Parenteral Injection 0.5% Marcaine Hydrochloride (Hospira) Parenteral Injection 0.5% Sensorcaine (AstraZeneca) Parenteral Injection 0.75% Bupivacaine Hydrochloride Injection (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Parenteral Injection 0.75% Marcaine-MPF Hydrochloride (Sanofi) Parenteral Injection 0.75% Sensorcaine-MPF (Astra-Zeneca)
Bupivacaine Hydrochloride in Dextrose Preparations Route of Administration Dosage Form Strength Brand or Generic Name (Manufacturer) Parenteral Injection 0.75% in 8.25% Dextrose Bupivacaine Spinal (Available from one or more manufacturer, distributor, and/or repackager by generic (nonproprietary) name) Parenteral Injection 0.75% in 8.25% Dextrose Marcaine Spinal (Hospira) Parenteral Injection 0.75% in 8.25% Dextrose Sensorcaine-MPF Spinal (AstraZeneca)
3.14 Exposure Standards and Regulations
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, including bupivacane hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Bupivacane hydrochloride/
3.15 Other Preventative Measures
Airborne exposure should be controlled primarily by engineering controls such as general dilution ventilation, local exhaust ventilation, or process enclosure. Local exhaust ventilation is generally preferred to general exhaust because it can control the contaminant at its source, preventing dispersion into the work area. An industrial hygiene survey involving air monitoring may be used to determine the effectiveness of engineering controls. Effectiveness of engineering controls intended for use with highly potent materials should be assessed by use of nontoxic surrogate materials Local exhaust ventilation such as a laboratory fume hood or other vented enclosure is recommended, particularly for grinding, crushing weighing, or other dust-generating procedures. /Bupivacaine hydrochloride/
As a general rule, when handling USP Reference Standards, avoid all contact and inhalation of dust, mists, and/or vapors associated with the material. Clean equipment and work surfaces with suitable detergent or solvent after use. After removing gloves, wash hands and other exposed skin thoroughly. /Bupivacaine hydrochloride/
For handling solutions, ensure that the glove material is protective against the solvent being used. Use handling practices that minimize direct hand contact. Employees who are sensitive to natural rubber (latex) should use nitrile or other synthetic nonlatex gloves. Use of powdered latex gloves should be avoided due to the risk of latex allergy. /Bupivacaine hydrochloride/
Maintain eyewash facilities in the work area. /Bupivacaine hydrochloride/
SRP: Contaminated protective clothing should be segregated in a manner that results in no direct personal contact by personnel who handle, dispose of, or clean the clothing. Quality assurance procedures to confirm the efficacy of the cleaning procedures should be implemented prior to the decontaminated protective clothing being returned for reuse by the workers. Contaminated clothing (including shoes/socks) should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
3.16 Protective Equipment and Clothing
Safety glasses with sideshields are recommended. Face shields or goggles may be required if splash potential exists or if corrosive materials are present. Approved eye protection (eg, bearing the ANSI Z87 or CSA stamp) is preferred. /Bupivacaine hydrochloride/
Where respirators are deemed necessary to reduce or control occupational exposures, use NIOSH-approved respiratory protection and have an effective respirator program in place. /Bupivacaine hydrochloride/
For handling of laboratory scale quantities, a cloth lab coat is recommended. Where significant quantities are handled, work clothing may be necessary to prevent take-home contamination. /Bupivacaine hydrochloride/
3.17 Specification

?Bupivacaine hydrochloride , its cas register number is 14252-80-3. It also can be called Bupivacaine hydrochloride [USAN] ; (+-)-1-Butyl-2',6'-pipecoloxylidide monohydrochloride,monohydrate ; 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, monohydrochloride, monohydrate ; Bupicacain hydrochlorid-1-wasser ; Bupivacaine ; Bupivacaine hydrochloride preservative free ; Marcaine hydrochloride ; Marcaine hydrochloride preservative free ; Marcaine spinal ; Sensorcaine .It is a?white solid.

3.18 Octanol/Water Partition Coefficient
log Kow = 3.41
3.19 Disposal Methods
SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.
4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 2

Acute toxicity - Dermal, Category 2

Acute toxicity - Inhalation, Category 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Danger

Hazard statement(s)

H300 Fatal if swallowed

H310 Fatal in contact with skin

H330 Fatal if inhaled

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P270 Do not eat, drink or smoke when using this product.

P262 Do not get in eyes, on skin, or on clothing.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P260 Do not breathe dust/fume/gas/mist/vapours/spray.

P271 Use only outdoors or in a well-ventilated area.

P284 [In case of inadequate ventilation] wear respiratory protection.

Response

P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026

P321 Specific treatment (see ... on this label).

P330 Rinse mouth.

P302+P352 IF ON SKIN: Wash with plenty of water/...

P310 Immediately call a POISON CENTER/doctor/\u2026

P361+P364 Take off immediately all contaminated clothing and wash it before reuse.

P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing.

P320 Specific treatment is urgent (see ... on this label).

Storage

P405 Store locked up.

P403+P233 Store in a well-ventilated place. Keep container tightly closed.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

7. Precursor and Product
product :
14252-80-3
14252-80-3
8. Computational chemical data
  • Molecular Weight:324.893g/mol
  • Molecular Formula:C18H29ClN2O
  • Compound Is Canonicalized:True
  • Exact Mass:324.197
  • Monoisotopic Mass:324.197
  • Complexity:321
  • Rotatable Bond Count:5
  • Hydrogen Bond Donor Count:2
  • Hydrogen Bond Acceptor Count:2
  • Topological Polar Surface Area:32.3A^2
  • Heavy Atom Count:22
  • Defined Atom Stereocenter Count:0
  • Undefined Atom Stereocenter Count:1
  • Defined Bond Stereocenter Count:0
  • Undefined Bond Stereocenter Count:0
  • Isotope Atom Count:0
  • Covalently-Bonded Unit Count:2
  • CACTVS Substructure Key Fingerprint: AAADceB7IAAEAAAAAAAAAAAAAAAAAAAAAAA8QAAAAAAAAAABAAAAHgAQAAAADCjBmAQywIPAAACI AiVSUACCAAAhAAAIiAGIRIgIYDLAkbGUIAhglADIyAcYiEAOAAACAAACAAAAAAQAAAQAAAAAAAAA AA==
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