94-24-6 | CAS DataBase

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94-24-6 Structure

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IdentificationMore[Name]

Tetracaine[CAS]

94-24-6[Synonyms]

2-(DIMETHYLAMINO)ETHYL 4-(N-BUTYLAMINO)BENZOATE
4-(BUTYLAMINO)BENZOIC ACID 2-(DIMETHYLAMINO)ETHYL ESTER
LABOTEST-BB LT00772366
TETRACAINE
TETRACAINE BASE
2-(Dimethylamino)ethyl 4-(butylamino)benzoate
2-(Dimethylamino)ethyl p-(butylamino)benzoate
2-Dimethylaminoethylester kyseliny p-butylaminobenzoove
2-dimethylaminoethylesterkyselinyp-butylaminobenzoove
2-dimethylaminoethylp-butylaminobenzoate
4-(butylamino)-benzoicaci2-(dimethylamino)ethylester
amethocaine
Anetain
Benzoic acid, 4-(butylamino)-, 2-(dimethylamino)ethyl ester
Benzoic acid, p-(butylamino)-, 2-(dimethylamino)ethyl ester
beta-Dimethylaminoethyl p-butylaminobenzoate
Contralgin
Diaethylaminoaethanol ester der p-butylaminobenzoesaeure
diaethylaminoaethanolesterderp-butylaminobenzoesaeure
Dicain[EINECS(EC#)]

202-316-6[Molecular Formula]

C15H24N2O2[MDL Number]

MFCD00053787[Molecular Weight]

264.36[MOL File]

94-24-6.molChemical PropertiesBack Directory[Appearance]

White or light-yellow, waxy solid. Very slightly soluble in water; soluble in alcohol, ether, benzene, chloroform.[Melting point ]

41.0 to 45.0 °C[Boiling point ]

407.59°C (rough estimate)[density ]

1.0200 (rough estimate)[refractive index ]

1.5800 (estimate)[storage temp. ]

2-8°C[solubility ]

soluble in Methanol[form ]

powder to crystal[pka]

pKa 8.33±0.03(H2O t = 20.0 I = 0.10 (KCl)) (Uncertain)[color ]

White to Almost white[Water Solubility ]

156mg/L(temperature not stated)[InChI]

InChI=1S/C15H24N2O2/c1-4-5-10-16-14-8-6-13(7-9-14)15(18)19-12-11-17(2)3/h6-9,16H,4-5,10-12H2,1-3H3[InChIKey]

GKCBAIGFKIBETG-UHFFFAOYSA-N[SMILES]

C(OCCN(C)C)(=O)C1=CC=C(NCCCC)C=C1[LogP]

3.510[CAS DataBase Reference]

94-24-6(CAS DataBase Reference)[NIST Chemistry Reference]

Tetracaine(94-24-6)Questions And AnswerBack Directory[Uses]

Tetracaine is used in assessing the potential for drug-nanoparticle surface interactions to improve drug penetration into the skin.[Description]

Tetracaine is a local anesthetic or numbing medicine that is used to numb the throat, eyes, or nose. Normally, the drug is administered before starting a surgery to decrease pain from the procedure. Tetracaine is applied to the eyes 30 minutes before the start of an intravenous and its effects can last up to 15 minutes. [Mechanism of Action]

Tetracaine acts by blocking the nerve systems. It does this by blocking the sodium ion channels needed for the conduction and initiation of neural impulses, thereby affecting the local anesthesia. Tetracaine acts by altering the function of calcium release channels that controls the release of calcium frim intracellular cells. [Precautions]

No studies have revealed whether the medicine can affect an unborn child; however, it is important to inform the doctor if pregnant while using it.

Informing the doctor is paramount if breastfeeding a baby, as no known research has illustrated whether tetracaine can pass into breast milk or harm a nursing baby.

To make tetracaine safe, it is important to inform the doctor if one has a history of spinal or brain injury, heart diseases, eye problems, a blood vessel disorder, open sores, skin injury in the area where the medicine will be applied.

Tetracaine should never be orally taken since it is typically designed for use on the skin only. If the medicine gets in the mouth, nose, vagina, or rectum, rinse with water. [Application]

Tetracaine topical (for the skin) is used to numb various body parts before a surgical procedure or a medical test. Conversely, tetracaine ophthalmic drops are used as local anesthetic for the eyes. [Dosage]

Always follow all direction on the prescription label. Do not use the medicine in smaller or larger amounts or for longer than recommended. [Side Effects]

Seek emergency medical advice in case of any of the following allergic reactions: difficult breathing, hives, swelling of the throat, tongue, lips, or face. Stop using the drug and call the physician if one has severe burning, swelling, stinging, or other irritation of the treated skin. Other alarming symptoms include eye watering, irritation, and increased sensitivity to light.

Common side effects include burning, stinging, or itching at the point of application of the medicine; numbness in places where tetracaine has been accidentally applied or skin redness or tenderness.

Nonclinical Toxicology
Studies conducted to reveal the genotoxicity of tetracaine have not indicated its mutagenesis, carcinogenicity, or impairment of fertility. Safety DataBack Directory[Hazard Codes ]

Xn,Xi[Risk Statements ]

R22:Harmful if swallowed.
R40:Limited evidence of a carcinogenic effect.
R42/43:May cause sensitization by inhalation and skin contact .
R43:May cause sensitization by skin contact.[Safety Statements ]

S22:Do not breathe dust .
S36/37:Wear suitable protective clothing and gloves .[RIDADR ]

UN 2811[WGK Germany ]

3[RTECS ]

DG4725000[HazardClass ]

6.1[PackingGroup ]

III[HS Code ]

29224999Hazard InformationBack Directory[Chemical Properties]

White or light-yellow, waxy solid. Very slightly soluble in water; soluble in alcohol, ether, benzene, chloroform.[Definition]

ChEBI: A benzoate ester in which 4-N-butylbenzoic acid and 2-(dimethylamino)ethanol have combined to form the ester bond; a local ester anaesthetic (ester caine) used for surface and spinal anaesthesia.[Biological Functions]

Tetracaine hydrochloride (Pontocaine) is an ester of PABA that is an effective topical local anesthetic agent and also is quite commonly used for spinal (subarachnoid) anesthesia. Epinephrine is frequently added to prolong the anesthesia.Tetracaine is considerably more potent and more toxic than procaine and cocaine. It has approximately a 5-minute onset and 2 to 3 hours of action.[General Description]

Tetracaine was developed to address the low potency andshort duration of action of procaine and chloroprocaine. The addition of the butyl side chain on the para nitrogen increasesthe lipid solubility of the drug and enhances the topical potencyof tetracaine. The plasma half-life is 120 to 150 seconds.Topically applied tetracaine to unbroken skin requires 30 to 45minutes to confer topical anesthesia. Tetracaine 4% gel is superiorthan eutectic mixture with lidocaine (EMLA) (an emulsionof lidocaine and prilocaine) in preventing pain associatedwith needle procedures in children. Tetracaine metabolism issimilar to procaine ester metabolism yielding parabutylaminobenzoicacid and dimethylaminoethanol and conjugatesexcreted in the urine. The pKa of the dimethylated nitrogen is8.4 and tetracaine is formulated as a hydrochloride salt with apH of 3.5 to 6.0. The increased absorption from topical siteshas resulted in reported toxicity. Overdoses of tetracaine mayproduce central nervous system (CNS) toxicity and seizure activitywith fatalities from circulatory depression reported.No selective cardiac toxicity is seen with tetracaine althoughhypotension has been reported. Tetracaine is employed for infiltrationanesthesia, spinal anesthesia, or topical use.[Biochem/physiol Actions]

Tetracaine also refers as 4-(Butylamino)benzoic acid 2-(dimethylamino)ethyl ester interfere with calcium movement in muscle and non-muscle cells and can inhibit potassium-induced as well as caffeine-induced shortening of outer hair cells (OHC′s). But, the product can′t inhibit electrically-induced shortening of OHC′s.The product can also stimulate caspase activation and inhibits pro-survival signalling pathways which in turn induce human renal cell apoptosis.[Veterinary Drugs and Treatments]

Tetracaine is more irritating than proparacaine but is sometimes used in veterinary medicine. It is indicated to produce local anesthesia of short duration for ophthalmic procedures including measurement of intraocular pressure (tonometry), removal of foreign bodies and sutures, and conjunctival and corneal scraping in diagnosis and gonioscopy. Tetracaine is also indicated to produce local anesthesia prior to surgical procedures in humans such as cataract extraction and pterygium excision, usually as an adjunct to locally injected anesthetics. Ophthalmic solutions used for intraocular procedures should be preservative-free. Preservatives may cause damage to the corneal epithelium if a significant quantity of solution enters the eye through the incision.Well-known Reagent Company Product InformationBack Directory[Sigma Aldrich]

94-24-6(sigmaaldrich)

1. Structure solution and refinement of tetracaine hydrochloride from X-ray powder diffraction data

Harriott Nowell, J. Paul Attfield,* New J. Chem., 2002, 26, 469–472

The crystal structure of tetracaine hydrochloride has been solved directly frompowder diffraction data using a global optimisation approach. The relatively large number of variables that were optimised in order to solve the crystal structure made this a challenging problem. Nevertheless, the structure was solved to a high degree of accuracy, in spite of the presence of a significant degree of preferred orientation in the sample, which introduces systematic errors into the solution process. The subsequent restrained Rietveld refinement made only small changes to the initial solution.

2. Solid-state assembly of carboxylic acid substituted pillar[5]arene and its host–guest complex with tetracaine

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Oksana Danylyuk* and Volodymyr Sashuk*. CrystEngComm,2015, 17,719–722

We have chosen tetracaine as a model drug to explore the ability of carboxylic PA5 to include large pharmaceutical molecules inside its macrocyclic cavity. Tetracaine is a potent anesthetic drug widely used in topical and spinal anesthesia, as well as in ophthalmology. However, as a local anesthetic, tetracaine shows a short duration of action and adverse side effects, such as cardiac and neurological toxicity, accompanied sometimes by skin or tissue irritation. In order to improve the applications of tetracaine, its inclusion into the macrocyclic cavities of cyclodextrins, p-sulfonatocalixarenes and cucurbiturils has been studied both in solution and in the solid state.

3. Solid-state interactions of calixarenes with biorelevant molecules

Oksana Danylyuk and Kinga Suwinska*. Chem. Commun., 2009, 5799–5813

In each case bilayer arrangements of host and guest molecules are observed. For tetracaine and tamoxifen all the guest molecules are located in the guest layer. However the interactions between the uncomplexed guest molecules and the host molecules are different in both structures. For tetracaine N–H…O hydrogen bonds occur between ‘free’ drug molecules and SO3- anionic groups of the para-sulfonatocalix[4]arene. Between guest molecules N–H…O hydrogen bonds as well as C–H…π and C–H…O interactions are present. In the crystal structure with tamoxifen no interactions between host and ‘free’ guest molecules exist; only C–H…π interactions occur between guest molecules.

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