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Dibucaine hydrochloride

Names

[ CAS No. ]:
61-12-1

[ Name ]:
Dibucaine hydrochloride

[Synonym ]:
2-Butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide hydrochloride (1:1)
Dibucaine hydrochloride
MFCD00012735
Benzolin (VAN)
Cincaine
benzolin
2-Butoxy-N-[2-(diethylamino)ethyl]-4-quinolinecarboxamide Monohydrochloride
4-Quinolinecarboxamide, 2-butoxy-N-[2-(diethylamino)ethyl]-, hydrochloride (1:1)
EINECS 200-498-1
2-Butoxy-N-[2-(diethylamino)ethyl]-4-quinolinecarboxamide hydrochloride (1:1)
2-butoxy-N-[2-(diethylamino)ethyl]quinoline-4-carboxamide,hydrochloride
Dibucaine HCl
Dibucaine (hydrochloride)

Biological Activity

[Description]:

Dibucaine Hydrochloride is a local anesthetic of the amide type now generally used for surface anesthesia.Target: Sodium ChannelDibucaine is an amide local anesthetic. Dibucaine reduced the degradation of BSA-gold complex in the reservosomes, which was not caused either by an inhibition of the whole proteolytic activity of the parasite or by a reduction on the expression levels of cruzipain [1].Dibucaine, a quaternary ammonium compound, inhibited SChE to a minimum within 2 min in a reversible manner. The inhibition was very potent. It had an IC(50) of 5.3 microM with BuTch or 3.8 microM with AcTch. The inhibition was competitive with respect to BuTch with a K(i) of 1.3 microM and a linear-mixed type (competitive/noncompetitive) with respect to AcTch with inhibition constants, K(i) and K(I) of 0.66 and 2.5 microM, respectively. Dibucaine possesses a butoxy side chain that is similar to the butryl group of BuTch and longer by an ethylene group from AcTch [2].

[Related Catalog]:

Signaling Pathways >> Membrane Transporter/Ion Channel >> Sodium Channel
Research Areas >> Neurological Disease
Natural Products >> Others

[References]

[1]. Souto-Padron, T., A.P. Lima, and O. Ribeiro Rde, Effects of dibucaine on the endocytic/exocytic pathways in Trypanosoma cruzi. Parasitol Res, 2006. 99(4): p. 317-20.

[2]. Elamin, B., Dibucaine inhibition of serum cholinesterase. J Biochem Mol Biol, 2003. 36(2): p. 149-53.


[Related Small Molecules]

EIPA | Riluzole | Ginsenoside Rg3 | Cariporide | Eleclazine hydrochloride | GS967 | Tenapanor | Triamterene | Ranolazine dihydrochloride | PF 05089771 | flecainide acetate | A-803467 | CNV1014802 (hydrochloride) | Zonisamide | Cinchocaine

Chemical & Physical Properties

[ Density]:
1.071g/cm3

[ Boiling Point ]:
496.3ºC at 760 mmHg

[ Melting Point ]:
99-101 °C(lit.)

[ Molecular Formula ]:
C20H30ClN3O2

[ Molecular Weight ]:
379.924

[ Flash Point ]:
254ºC

[ Exact Mass ]:
379.202667

[ PSA ]:
54.46000

[ LogP ]:
4.67820

[ Storage condition ]:
Refrigerator

[ Stability ]:
Stable. Incompatible with strong oxidizing agents. Protect from moisture.

MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
GD3325000
CHEMICAL NAME :
Cinchoninamide, 2-butoxy-N-(2-(diethylamino)ethyl)-, monohydrochloride
CAS REGISTRY NUMBER :
61-12-1
LAST UPDATED :
199707
DATA ITEMS CITED :
17
MOLECULAR FORMULA :
C20-H29-N3-O2.Cl-H
MOLECULAR WEIGHT :
379.98
WISWESSER LINE NOTATION :
T66 BNJ CO4 EVM2N2&2 &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration into the eye
SPECIES OBSERVED :
Rodent - rabbit
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
22 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
27 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
52 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
29 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
25400 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
3800 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
7743 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
2 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
5 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraspinal
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
2 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
15300 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
3097 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Parenteral
SPECIES OBSERVED :
Amphibian - frog
DOSE/DURATION :
55 mg/kg
TOXIC EFFECTS :
Peripheral Nerve and Sensation - spastic paralysis with or without sensory change Behavioral - changes in motor activity (specific assay) Cardiac - other changes
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Bird - wild bird species
DOSE/DURATION :
42 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value

MUTATION DATA

TYPE OF TEST :
DNA adduct
TEST SYSTEM :
Bacteria - Escherichia coli
DOSE/DURATION :
15 umol/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 89,95,1981 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - M1054 No. of Facilities: 308 (estimated) No. of Industries: 4 No. of Occupations: 4 No. of Employees: 2429 (estimated)

Safety Information

[ Symbol ]:

GHS05, GHS07

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H318

[ Precautionary Statements ]:
P280-P305 + P351 + P338

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Faceshields;Gloves

[ Hazard Codes ]:
Xn:Harmful

[ Risk Phrases ]:
R22;R41

[ Safety Phrases ]:
S26-S39

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
GD3325000

[ HS Code ]:
2934999090

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%


Related Compounds