| Identification | Back Directory | [Name]
Dimethocaine | [CAS]
94-15-5 | [Synonyms]
NSC 68927
Larocaine
Dimercaine
Brn 2215967
DiMethocine
Dimethocaine
dimethylcaine
Larocaine 99%
Dimethocaine>
Larocaine 94-15-5
Dimethocaine/Larocaine
Larocaine dimethocaine
553-63-9 (Hydrochloride)
High Purity 99% Dimethocaine
Dimethocaine Basic information
lidocaine benzocaine sevoflurane
Larocaine dimethocaine anesthetic
LAROCAINE; NSC 68927; BRN 2215967
2-[(diethylamino)methyl]-2-methyl-
China Factroy Supply 99%Pure Dimethocaine Powder
3-Diethylamino-2,2-dimethylpropyl 4-aminobenzoate
(3-Diethylamino-2,2-dimethyl)propyl 4-aminobenzoat
p-Aminobenzoic acid 3-(diethylamino)-2,2-dimethylpropyl
3-(Diethylamino)-2,2-dimethyl-1-propanol p-aminobenzoate
4-Aminobenzoesaeure-3-diethylamino-2,2-dimethylproplylester
1-Propanol, 3-(diethylamino)-2,2-dimethyl-, p-aminobenzoate
4-Aminobenzoic acid 3-(diethylamino)-2,2-dimethylpropyl ester
p-Aminobenzoic acid 3-(diethylamino)-2,2-dimethylpropyl ester
2-[(diethylaMino)Methyl]-2-Methyl-1-Propanol 1-(4-aMinobenzoate)
1-Propanol, 3-(diethylamino)-2,2-dimethyl-, 4-aminobenzoate (ester)
1-Propanol, 2-[(diethylamino)methyl]-2-methyl-, 1-(4-aminobenzoate)
1-Propanol, 3-(diethylamino)-2,2-dimethyl-, p-aminobenzoate (ester) (8ci)
1-Propanol, 3-(diethylamino)-2,2-dimethyl-, 4-aminobenzoate (ester) (9ci)
Larocaine
3-Diethylamino-2,2-dimethylpropyl 4-Aminobenzoate
4-Aminobenzoic Acid 3-Diethylamino-2,2-dimethylpropyl Ester | [EINECS(EC#)]
1592732-453-0 | [Molecular Formula]
C16H26N2O2 | [MDL Number]
MFCD01697030 | [MOL File]
94-15-5.mol | [Molecular Weight]
278.39 |
| Chemical Properties | Back Directory | [Melting point ]
53.0 to 57.0 °C | [Boiling point ]
421.21°C (rough estimate) | [density ]
1.035 | [refractive index ]
1.5290 (estimate) | [storage temp. ]
Refrigerator | [solubility ]
Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | [form ]
Solid | [pka]
10.08±0.25(Predicted) | [color ]
Pale Orange to Light Orange | [Merck ]
14,3221 | [InChI]
InChI=1S/C16H26N2O2/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 | [InChIKey]
OWQIUQKMMPDHQQ-UHFFFAOYSA-N | [SMILES]
C(OC(=O)C1=CC=C(N)C=C1)C(CN(CC)CC)(C)C | [CAS DataBase Reference]
94-15-5 |
| Hazard Information | Back Directory | [Description]
Dimethocaine, also known as DMC or larocaine, is a compound with a stimulatory effect. This effect resembles that of cocaine, although dimethocaine appears to be less potent. Just like cocaine, dimethocaine is addictive due to its stimulation of the reward pathway in the brain. However, dimethocaine is a legal cocaine replacement in some countries and is even listed by the European Monitoring Centre for Drugs and Drug Addiction (EMCDDA) under the category “synthetic cocaine derivatives”. The structure of dimethocaine, being a 4-aminobenzoic acid ester, resembles that of procaine. It is found as a white powder at room temperature. | [Chemical Properties]
Dimethocaine is a yellow chrystalline powder. It is soluble in organic solvents such as ethanol, DMSO, and dimethyl formamide, which should be purged with an inert gas. | [Uses]
Dimethocaine is a local anesthetic with stimulatory properties that is half the potency of cocaine. | [Definition]
ChEBI: Dimethocaine is a benzoate ester. It is derivate from cocaine, it is not a part of the organic alkaloid mix coming from a coca plant. It is very popular research chemical, mainly used as local anesthetic, but also the stimulant qualities appeared to be shown immediately. | [Biological Activity]
Dimethocaine is a local anesthetic that, because of its similarity in action to cocaine, has potential for abuse. This compound completely inhibits dopamine uptake in rat striatal synaptosomes with an IC50 value of 1.2 μM comparable to that of cocaine (IC50 = 0.7 μM). As a result, dimethocaine dose-dependently substitutes for cocaine in drug discrimination tests in rats and rhesus monkeys. This product is intended for forensic and research purposes. | [Side effects]
The side effects include tachycardia, difficulty with breathing, pain in the chest, vasoconstriction, insomnia, paranoia and anxiety. | [Metabolism]
Dimethocaine (DMC), a synthetic derivative of cocaine, is distributed and consumed as "new psychoactive substance" (NPS). It is mainly metabolized by N-acetylation, N-deethylation or hydroxylation. As DMC is metabolized via two main steps and different P450 isoforms were involved in the hepatic clearance of DMC, a clinically relevant interaction with single P450 inhibitors should not be expected. However, a slow acetylation phenotype or inhibition of NAT2 could lead to decreased N-acetylation and hence leading to an increased risk of side effects caused by this arylamine. Using the relative activity factor approach, the net clearances for deethylation of DMC were calculated to be 3% for P450 1A2, 1% for 2C19,<1% for 2D6, and 96% for 3A4. The net clearances for hydroxylation of DMC were calculated to be 32% for P450 1A2, 5% for 2C19, 51% for 2D6, and 12% for 3A4[1].
| [References]
[1] Markus R Meyer, Hans H Maurer, Carina Lindauer. “Dimethocaine, a synthetic cocaine derivative: studies on its in vitro metabolism catalyzed by P450s and NAT2.” Toxicology letters 225 1 (2014): 139–46. |
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