Description
Dimethocaine hydrochloride is a synthetic compound that belongs to the class of local anesthetics. It has gained tremendous attention from researchers in the recent past, mainly because of its potential applications in the fields of medicine, pharmacology, and forensic science.
This paper provides an in-depth analysis of dimethocaine hydrochloride, examining its definition and background, physical and chemical properties, synthesis, characterization, analytical methods, biological properties, and toxicity and safety in scientific experiments. The paper will also explore the current state of research, potential implications in various fields of research and industry, limitations, and future directions.
Definition And Background
Dimethocaine hydrochloride is a synthetic type of ester that is classified as a local anesthetic. It is also known as larocaine, dimethocaine powder, or DMC. The compound has an anesthetic potency that is about ten times greater than cocaine and is less toxic.
It was first synthesized in the 1930s, and its pharmacological properties have been a subject of study since then. Studies have shown that dimethocaine hydrochloride has a high affinity for the dopamine transporter, which is the same target for cocaine.
Physical And Chemical Properties
Dimethocaine hydrochloride has a molecular formula of C16H26N2O2. It is a white crystalline powder that has a melting point of 156-158°C. It is soluble in alcohol, chloroform, and ether, but practically insoluble in water.
The compound has a pKa value of 8.9 and a logP value of 2.8. The logP value indicates that the compound has a moderate lipophilicity.
Synthesis and Characterization
Dimethocaine hydrochloride can be synthesized by a one-pot reaction involving the reaction of an appropriate p-nitrobenzoyl ester with piperidine. The reaction involves the reduction of the nitro group under basic conditions, followed by the introduction of a hydrazide molecule. The hydrazide molecule then reacts with the intermediate to form the final product, dimethocaine hydrochloride.
The characterization of dimethocaine hydrochloride can be done using various techniques such as nuclear magnetic resonance (NMR), Fourier-transform infrared spectroscopy (FTIR), and mass spectrometry (MS). NMR provides detailed information about the structure and conformational properties of the compound. FTIR helps in identifying functional groups present in the compound, while MS helps in determining the molecular weight and fragmentation pattern of the compound.
General Information
CAS Number
553-63-9
Product Name
Dimethocaine hydrochloride
IUPAC Name
[3-(diethylamino)-2,2-dimethylpropyl] 4-aminobenzoate;hydrochloride
Molecular Formula
C16H27ClN2O2
Molecular Weight
314.8 g/mol
InChI
InChI=1S/C16H26N2O2.ClH/c1-5-18(6-2)11-16(3,4)12-20-15(19)13-7-9-14(17)10-8-13;/h7-10H,5-6,11-12,17H2,1-4H3;1H
InChI Key
WWTWKTDXBNHESE-UHFFFAOYSA-N
SMILES
CCN(CC)CC(C)(C)COC(=O)C1=CC=C(C=C1)N.Cl
Solubility
DMSO (Slightly), Water (Slightly)
Synonyms
1-Aminobenzoyl-2,2-dimethyl-3-diethylaminopropanol Hydrochloride; 3-Diethylamino-2,2-dimethylpropyl p-aminobenzoate Hydrochloride; Diethylaminoneopentyl Alcohol Hydrochloride p-Aminobenzoate; Larocaine Hydrochloride;
Canonical SMILES
CCN(CC)CC(C)(C)COC(=O)C1=CC=C(C=C1)N.Cl
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