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Dibucaine

HCID 3025
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
85-79-0
Standard SMILES
CCCCOc1cc(C(=O)NCCN(CC)CC)c2ccccc2n1
InChIKey
PUFQVTATUTYEAL-UHFFFAOYSA-N
Molecular formula
C20H29N3O2
Average molar mass
343.5 g/mol
Monoisotopic mass
343.22597718

Overview

Cinchocaine is a monocarboxylic acid amide that is the 2-(diethylamino)ethyl amide of 2-butoxyquinoline-4-carboxylic acid. One of the most potent and toxic of the long-acting local anesthetics, its parenteral use was restricted to spinal anesthesia. It is now generally only used (usually as the hydrochloride) in creams and ointments and in suppositories for temporary relief of pain and itching associated with skin and anorectal conditions. It has a role as a topical anaesthetic. It is a monocarboxylic acid amide, an aromatic ether and a tertiary amino compound.

Names & identifiers

Preferred name
Dibucaine
IUPAC
2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide
English name
Cinchocaine
Molecular formula
C20H29N3O2
Molecular weight
343.46

Names & synonyms

dibucaineCinchocaine85-79-0NupercainalDermacaineDibucaine BaseDibucain2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamideCinchocainumCincocainaCincocainioDibucaine [USP]
Show more names
percamineINN / BANNupercaineZinn cocaine
2-butoxy-N-(2-(diethylamino)ethyl)quinoline-4-carboxamide2-Butoxyquinoline-4-carboxylic acid diethylaminoethylamideDibucaine (USP)DTXSID30452712-Butoxy-N-(2-(diethylamino)ethyl)cinchoninamide2-Butoxy-N-(beta-diethylaminoethyl)cinchoninamide2-N-Butoxy-N-(2-diethylaminoethyl)cinchoninamideN-(2-(Diethylamino)ethyl)-2-butoxycinchoninamide

Database identifiers

CAS
85-79-0
PubChem CID
3025
DTXSID
DTXSID3045271
ChEMBL
CHEMBL1086
ChEBI
CHEBI:247956
UNII
L6JW2TJG99
EC Number
201-632-1
Nikkaji
J3.887C

Properties

Computed structural properties

XLogP
4.4
Topological polar surface area
54.5 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
10
Heavy atoms
25
Formal charge
0
Complexity
387

Experimental & physicochemical properties

Drugs · 2 items

Pharmaceuticals

Pharmaceuticals -> Listed in ZINC15

SpringerMaterials PropertiesNuclear quadrupole resonance spectroscopy
LogP · 3 items

log Kow= 4.40

4.2

4.19

OdorOdorless
Color/FormColorless or almost colorless powder
Solubility · 5 items

Hydroscopic crystals; decomp @ 90-98 °C; faintly alkaline to litmus (aq soln, 1 in 20); freely sol in alc, acetone, chloroform; sol in 0.5 part water; slightly sol in benzene, ethyl acetate, toluene (on warming); insol in ether, oils /Dibucaine hydrochloride/

INSOL IN WATER; SOL IN ETHANOL, CHLOROFORM, ETHER, PETROLEUM ETHER

Soluble in alcohol and acetone; slightly soluble in water.

3.89e-02 g/L

>51.5 [ug/mL] (The mean of the results at pH 7.4)

Human Drugs · 2 items

Breast Feeding; Lactation; Anesthetics, Local

Pharmaceuticals

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Danger

H302 (92.7%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P264+P265, P270, P280, P301+P317, P305+P354+P338, P317, P330, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

REACH registered substance: Cinchocaine (EC: 201-632-1)

Cinchocaine: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 4-Quinolinecarboxamide, 2-butoxy-N-[2-(diethylamino)ethyl]-: Environment tier I assessment
FDA Requirements · 1 item

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Hazard Classes and CategoriesAcute Tox. 4 (92.7%)

Safety & protection

Disposal Methods · 1 item

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Chemistry & industry

Pharmacology

ATC Code · 6 items

N - Nervous system

D - Dermatologicals

S - Sensory organs

S - Sensory organs

C - Cardiovascular system

QD - Dermatologicals

PharmacodynamicsDibucaine is an amide-type local anesthetic, similar to lidocaine.
Mechanism of Action · 6 items

Local anesthetics block both the initiation and conduction of nerve impulses by decreasing the neuronal membrane's permeability to sodium ions through sodium channel inhibition. This reversibly stabilizes the membrane and inhibits depolarization, resulting in the failure of a propagated action potential and subsequent conduction blockade.

... PREVENT THE GENERATION & THE CONDUCTION OF THE NERVE IMPULSE. THEIR PRIMARY SITE OF ACTION IS THE CELL MEMBRANE. ... BLOCK CONDUCTION BY DECREASING OR PREVENTING THE TRANSIENT INCREASE IN THE PERMEABILITY OF EXCITABLE MEMBRANES TO NA IONS THAT IS NORMALLY PRODUCED BY A SLIGHT DEPOLARIZATION ... /LOCAL ANESTHETICS/

AS ANESTHETIC ACTION PROGRESSIVELY DEVELOPS IN A NERVE, THE THRESHOLD FOR ELECTRICAL EXCITABILITY GRADUALLY INCREASES, THE RATE OF RISE OF THE ACTION POTENTIAL DECLINES, IMPULSE CONDUCTION SLOWS, & THE SAFETY FACTOR FOR CONDUCTION DECREASES; THESE FACTORS DECREASE PROBABILITY OF PROPAGATION OF THE ACTION POTENTIAL, AND NERVE CONDUCTION FAILS. /LOCAL ANESTHETICS/

... CAN BLOCK K ION CHANNELS. ... BLOCKADE OF CONDUCTION IS NOT ACCOMPANIED BY ANY LARGE OR CONSISTENT CHANGE IN RESTING MEMBRANE DUE TO BLOCK OF K ION CHANNELS. /LOCAL ANESTHETICS/

... SITE AT WHICH LOCAL ANESTHETICS ACT, AT LEAST IN THEIR CHARGED FORM, IS ACCESSIBLE ONLY FROM THE INNER SURFACE OF THE MEMBRANE. ... LOCAL ANESTHETICS APPLIED EXTERNALLY FIRST MUST CROSS THE MEMBRANE BEFORE THEY CAN EXERT A BLOCKING ACTION. /LOCAL ANESTHETICS/

... ACT ON ANY PART OF NERVOUS SYSTEM & ON EVERY TYPE OF NERVE FIBER. /LOCAL ANESTHETICS/

Metabolism/Metabolites · 2 items

Primarily hepatic.

METABOLISM OF AMIDE-LINKED LOCAL ANESTHETICS IS MORE COMPLEX /THAN ESTER TYPES/ ...

FDA Pharmacological Classification · 6 items

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Decomposition
When heated to decomposition it emits toxic fumes of nitroxides.
Melting Point · 4 items

99-101 °C (HCl salt)

64 °C

Melting point: 62-65 °C

99 - 101 °C (hydrochloride salt)

Physical DescriptionSolid
Stability/Shelf LifeSENSITIVE TO LIGHT
Dissociation Constants8.85

Physicochemical properties

Melting point
64 ° · 64°
Boiling point
478.73 °C · 478.73°C (rough estimate)
Density
1.1145 · 1.1145 (rough estimate)
refractive index
1.63 · 1.6300 (estimate)
storage temp.
-20 °C · Store at -20°C
solubility
45 · DMSO:45.0(Max Conc. mg/mL);131.02(Max Conc. mM)
pka
-5.3 · pKa -5.3(aq. H2SO4) (Uncertain)
form
Solid:particulate/powder
color
White to yellow
Water Solubility
68.01 mg/L · 68.01mg/L(temperature not stated)
InChI
InChI=1S/C20H29N3O2/c1-4-7-14-25-19-15-17(16-10-8-9-11-18(16)22-19)20(24)21-12-13-23(5-2)6-3/h8-11,15H,4-7,12-14H2,1-3H3,(H,21,24)
InChIKey
PUFQVTATUTYEAL-UHFFFAOYSA-N
SMILES
N1C2C(=CC=CC=2)C(C(NCCN(CC)CC)=O)=CC=1OCCCC
LogP
4.4 at · 4.4 at 25℃ and pH7
CAS DataBase Reference
85 · 85-79-0(CAS DataBase Reference)
FDA 21 CFR
310.545 · 310.545
FDA UNII
6 JW2TJG99 · L6JW2TJG99
ATC code
5 AD04,D04AB02,N01BB06,S01HA06,S02DA04 · C05AD04,D04AB02,N01BB06,S01HA06,S02DA04
NIST Chemistry Reference
Dibucaine(85-79-0)
Symbol(GHS)
7 · GHS07,GHS05
Signal word
Danger
Hazard statements
302 · H302-H318
Precautionary statements
264 · P264-P270-P301+P312-P330-P501-P280-P305+P351+P338-P310
Hazard Codes
Xn
Risk Statements
22 · 22-41
Safety Statements
26 · 26-39
RTECS
3150000 · GD3150000
Hazardous Substances Data
85 · 85-79-0(Hazardous Substances Data)
REACH Registrations
Active

Toxicology

Interactions · 2 items

... DURATION OF ACTION /OF SPINAL ANESTHESIA/ ... MAY BE INCREASED ... BY ADDING EPINEPHRINE TO THE SOLUTION. /LOCAL ANESTHETICS/

BY DECREASING THE RATE OF ABSORPTION, /EPINEPHRINE/ NOT ONLY LOCALIZES THE ANESTHETIC AT THE DESIRED SITE BUT ALSO ALLOWS THE RATE AT WHICH IT IS DESTROYED IN THE BODY TO KEEP PACE WITH THE RATE AT WHICH IT IS ABSORBED INTO THE CIRCULATION. THIS REDUCES ITS SYSTEMIC TOXICITY. /LOCAL ANESTHETICS/

Human Toxicity Excerpts · 2 items

DIBUCAINE HCL CAUSED PHOTOALLERGIC DERMATITIS IN 13-YR-OLD GIRL WHEN USED AS LOCAL ANESTHETIC IN TREATMENT OF DENTAL CARIES.

A 2-year-old child apparently ingested dibucaine hydrochloride (0.5% Nupercainal Cream), acted strangely, staggered, then seized, became cyanotic, vomited, developed a cardiorespiratory arrest, and died. /Dibucaine hydrochloride/

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Non-Human Toxicity Values · 4 items

LD50 Mouse ip 24,500 ug/kg

LD50 Mouse sc 28,500 ug/kg

LD50 Rabbit sc 8500 ug/kg

LD50 Rabbit iv 2500 ug/kg

Regulatory information

FDA Requirements · 1 item

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

Safety data

rtecs
GD3150000
risk_code
22-41
Signal word
Danger
Symbol(GHS)
GHS07,GHS05
hazard_code
Xn
safety_code
26-39
Hazard statements
H302-H318
REACH Registrations
Active
Precautionary statements
P264-P270-P301+P312-P330-P501-P280-P305+P351+P338-P310
Hazardous Substances Data
85-79-0(Hazardous Substances Data)

L6JW2TJG99

DIBUCAINE

Established Pharmacologic Class [EPC] - Standardized Chemical Allergen

Physiologic Effects [PE] - Increased Histamine Release

Physiologic Effects [PE] - Cell-mediated Immunity

Chemical Structure [CS] - Allergens

MeSH Pharmacological Classification · 1 item

Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate.

Absorption, Distribution and Excretion · 5 items

In general, ionized forms (salts) of local anesthetics are not readily absorbed through intact skin. However, both nonionized (bases) and ionized forms of local anesthetics are readily absorbed through traumatized or abraded skin into the systemic circulation.

THE DRUG IS PARTIALLY METABOLIZED & A PORTION IS ELIMINATED UNCHANGED.

... RADIOACTIVE /SPINAL/ LOCAL ANESTHETICS ARE CONCN WITHIN SPINAL NERVE ROOTS AS WELL AS POSTERIOR & LATERAL COLUMNS OF SPINAL CORD. ... RATE OF ENZYMATIC HYDROLYSIS OF LOCAL ANESTHETIC AGENTS BY SPINAL FLUID IS SLOW. /LOCAL ANESTHETICS/

DURATION ... DEPENDS UPON RATE @ WHICH DRUG IS REMOVED FROM CEREBROSPINAL FLUID & FROM NERVE ROOTS WHERE IT EXERTS ITS ACTION. /LOCAL ANESTHETICS/

AT AUTOPSY, DIBUCAINE WAS DEMONSTRATED FROM UPPER SPINAL CORD (3.11 MUG/0.1 G), LOWER SPINAL CORD (7.15 MUG/0.1 G), LIVER (0.299 MUG/1.0 G) & KIDNEY (0.181 MUG/1.0 G).

Cellular LocationsCytoplasm
Metabolite PathwaysDibucaine Action Pathway

Uses & manufacturing

Uses · 4 items

MEDICATION (VET)

Therap cat: Anesthetic (local) /Hydrochloride/

Medicine (anesthetic)

Use (kg; approx.) in Germany (2009): >100

Methods of Manufacturing · 2 items

Miescher, US patent 1,825,623 (1931 to Ciba). /Dibucaine hydrochloride/

Quinoline derivative

Formulations/Preparations · 4 items

NUPERCAINAL (CIBA), TOPICAL: CREAM 0.5% WITH ACETONE SODIUM BISULFITE 0.37% IN 1.5 OZ CONTAINERS; OINTMENT 1% WITH ACETONE BISULFITE 0.5% IN 1 & 2 OZ CONTAINERS; AEROSOL SPRAY 0.25% WITH ALCOHOL 46% IN 6 OZ CONTAINERS; SUPPOSITORIES 2.5 MG /DIBUCAINE HCL/

BUCACET (LEMMON): EACH LOZENGE CONTAINS DIBUCAINE HCL 0.5 MG & CETALKONIUM CHLORIDE 4 MG. /DIBUCAINE HCL/

Grade: NF

Also available as the hydrochloride.

Use ClassificationPharmaceuticals
General Manufacturing Information · 2 items

A SPECTROPHOTOMETRIC TEST /FOR ATYPICAL CHOLINESTERASE/ WAS DEVELOPED BY KALOW & GENEST (1957) WHICH INCL DIBUCAINE AS AN INHIBITOR...MADE IT POSSIBLE TO IDENTIFY TYPE OF ESTERASE PRESENT IN TEST SERA...ALSO...TO DETECT HETEROZYGOUS CARRIERS OF /ATYPICAL ESTERASE/ TRAIT.

...toxicity resulted in its removal from the U.S. market as an injectable preparation ... It is currently available as a cream and an ointment for use on the skin.

Applications · 2 items

UsesCinchocaine is a local anesthesic,used for Na+ channel blocker.

General DescriptionArticaine has a secondary nitrogen with a pKa of 7.8. It containsan aromatic thiophene ring bioisostere of the phenylring found in most other amide anesthetics. The log P of abenzene ring is 2.13 and the thiophene ring log P is 1.81,thus the thiophene ring is more hydrophilic than a phenylring. Although the thiophene ring has less lipid solubilitythan a phenyl ring, articaine is a lipid-soluble compound dueto the propylamine, the branched methyl and the substitutionson the thiophene ring. The onset of action of articaineis similar to lidocaine’s onset of action.

Preparation methods · 1 item

Preparation1. Synthesis of 2-chloro-N-[2-(diethylamino)ethyl]-4-quinoline carboxamide At room temperature, 200 g of 2-hydroxy-4-quinoline carboxylic acid and 1500 ml of toluene were added dropwise to a 3000 ml three-necked flask with stirring. The mixture was heated to 75 °C and reacted for 2 hours. The temperature was lowered to 25 °C and concentrated under reduced pressure. Then, 500 ml of toluene was added and the mixture was concentrated to dryness under reduced pressure. The solution was diluted directly with 2000 ml of toluene and added to a 5000 ml three-necked flask. 100 g of N,N-diethyldiethylamine was added. The mixture was heated to 70 °C and stirred until the reaction was complete. The temperature was lowered to room temperature, water was added and stirred for 30 minutes. The mixture was separated into liquid and liquid layers. The organic layer was washed twice with water and once with saturated brine. The solution was dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated to dryness to obtain 274 g of 2-chloro-N-[2-(diethylamino)ethyl]-4-quinoline carboxamide, i.e., octocamide, with a yield of 85%. 2. Synthesis of Cincocaine 200g of cincoamide, 550ml of n-butanol, and 300g of sodium n-butoxide were added to a 3000ml reaction flask. The mixture was gradually heated to reflux for 3 hours, then cooled to room temperature. 1000ml of purified water was added, and the mixture was stirred for 30 minutes. After standing for 30 minutes to separate the layers, the aqueous layer was discarded. The organic layer was dried with anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. Then, 500ml of toluene was added, and the mixture was heated to 60℃ and stirred for 30 minutes. After standing, the layers separated. The upper toluene layer was cooled to crystallize, yielding 146g of purified Cinchocaine, with a yield of 65% and a purity of 99.7%.

Upstream & downstream products

Upstream raw materials

2-Chloro-N-[2-(diethylamino)ethyl]-4-quinolinecarboxamide1-ButanolSodium hydroxideHexane

Downstream products

Dibucaine hydrochloride

Suppliers100 total

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Shanghai Biolang Biotechnology Co., Ltd.+86-15970428662 +86-13397199602 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
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Additional notes · 1 item

DefinitionChEBI: A monocarboxylic acid amide that is the 2-(diethylamino)ethyl amide of 2-butoxyquinoline-4-carboxylic acid. One of the most potent and toxic of the long-acting local anesthetics, its parenteral use was restricted to spinal anesthesia. It is now generally o ly used (usually as the hydrochloride) in creams and ointments and in suppositories for temporary relief of pain and itching associated with skin and anorectal conditions.