Dimethocaine (hydrochloride)
(Synonyms: 盐酸二甲卡因,Larocaine hydrochloride) 目录号 : GC43465
An Analytical Reference Standard
Cas No.:553-63-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
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.
| Cas No. | 553-63-9 | SDF | |
| 别名 | 盐酸二甲卡因,Larocaine hydrochloride | ||
| Canonical SMILES | NC1=CC=C(C(OCC(C)(C)CN(CC)CC)=O)C=C1.Cl | ||
| 分子式 | C16H26N2O2•HCl | 分子量 | 314.9 |
| 溶解度 | DMF: 20 mg/ml,DMSO: 14 mg/ml,Ethanol: 16 mg/ml,PBS (pH 7.2): 10 mg/ml | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.1756 mL | 15.8781 mL | 31.7561 mL |
| 5 mM | 0.6351 mL | 3.1756 mL | 6.3512 mL |
| 10 mM | 0.3176 mL | 1.5878 mL | 3.1756 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Dimethocaine, a synthetic cocaine derivative: studies on its in vitro metabolism catalyzed by P450s and NAT2
Toxicol Lett 2014 Feb 10;225(1):139-46.PMID:24309420DOI:10.1016/j.toxlet.2013.11.033.
Dimethocaine (DMC), a synthetic derivative of cocaine, is distributed and consumed as "new psychoactive substance" (NPS) without any safety testing at the forefront. It is mainly metabolized by N-acetylation, N-deethylation or hydroxylation. Therefore, the aim of the presented study was to determine the human NAT and P450 isozymes involved in this major metabolic steps, to measure the kinetics of the reactions, and to estimate the contribution on in vivo hepatic clearance. For these studies, cDNA-expressed NATs and P450s were used and formation of metabolites after incubation was measured using LC-MS or LC-MS(n). For N-acetylation, NAT2 could be shown to be the only isoform catalyzing the reaction in vitro hence assuming to be the only relevant enzyme for in vivo acetylation. Kinetic profiles of all P450 catalyzed metabolite formations followed classic Michaelis-Menten behavior with enzyme affinities (Km values) between 3.6 and 220 μM. 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. Furthermore, these data were confirmed by chemical inhibition tests in human liver microsomes. 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.
Stimulant activities of Dimethocaine in mice: reinforcing and anxiogenic effects
Psychopharmacology (Berl) 1996 Oct;127(4):323-7.PMID:8923567DOI:10.1007/s002130050093.
The present study evaluated the effects of Dimethocaine and procaine, esteratic local anesthetics, on locomotor activity, conditioned place preference and on the elevated plus-maze test of anxiety in mice, behavioral tests believed to be sensitive to cocaine action. Acute administration of Dimethocaine (10-40 mg/kg, IP) significantly increased locomotor activity and time spent on the drug-paired side and reduced the relative number of entries and time spent on the open arms of the plus-maze in mice. Procaine (20-50 mg/kg, IP) failed to affect these responses. These data demonstrate the locomotor stimulant, reinforcing and anxiogenic actions of Dimethocaine similar to those reported for cocaine in animals. In addition, these findings support a role for dopaminergic activity, rather than local anesthetic action, in the behavioral effects caused by Dimethocaine.
Dimethocaine, a synthetic cocaine analogue: studies on its in-vivo metabolism and its detectability in urine by means of a rat model and liquid chromatography-linear ion-trap (high-resolution) mass spectrometry
Anal Bioanal Chem 2014 Mar;406(7):1845-54.PMID:24448968DOI:10.1007/s00216-013-7539-0.
Dimethocaine (DMC, larocaine), a synthetic derivative of cocaine, is a widely distributed "legal high" consumed as a "new psychoactive substance" (NPS) without any safety testing, for example studies of metabolism. Therefore, the purpose of this work was to study its in-vivo and in-vitro metabolism by use of liquid chromatography-(high resolution) mass spectrometry (LC-HRMS(n)). DMC was administered to male Wistar rats (20 mg kg(-1)) and their urine was extracted either by solid-phase extraction after enzymatic cleavage of conjugates or by use of protein precipitation (PP). The metabolites were separated and identified by LC-HRMS(n). The main phase I reactions were ester hydrolysis, deethylation, hydroxylation of the aromatic system, and a combination of these. The main phase II reaction was N-acetylation of the p-aminobenzoic acid part of the unchanged parent compound and of several phase I metabolites. The metabolites identified were then used for identification of DMC in rat urine after application of a common user's dose. By use of GC-MS and LC-MS(n) standard urine-screening approaches (SUSAs), DMC and its metabolites could be detected in the urine samples.
The effects of systemic procaine, lidocaine and Dimethocaine on nociception in mice
Gen Pharmacol 1996 Jun;27(4):647-50.PMID:8853299DOI:10.1016/0306-3623(95)02079-9.
1. Different local anesthetics were tested for analgesic activity in three antinociceptive models, the acetic acid-induced abdominal constriction, tail-flick and hot plate tests in the mouse. 2. In the abdominal constriction test, subcutaneous, SC, injection of lidocaine (10, 20 or 30 mg/kg) and Dimethocaine (5, 10 or 20 mg/kg) induced dose-dependent antinociceptive responses. Procaine (20, 30 or 50 mg/kg) was also able to reduce the response to noxious chemical stimuli. 3. The IP injection of lidocaine and Dimethocaine significantly inhibited the tail-flick and paw-licking hot plate responses; procaine was weak or inactive in these tests, in which heat was the noxious stimulus. 4. Taken together, these results suggest that antinociception produced by systemically administered lidocaine and Dimethocaine at nontoxic doses in mice is due, at least in part, to their central effects.
Cocaine-like discriminative stimulus effects of procaine, Dimethocaine and lidocaine in rats
Psychopharmacology (Berl) 1993;110(3):287-94.PMID:7831421DOI:10.1007/BF02251283.
The discriminative stimulus effects of several local anesthetics and (+)-amphetamine were assessed in a drug discrimination based on the psychomotor stimulant cocaine. Two groups of adult male Sprague-Dawley rats were trained in two-lever operant chambers in a cocaine versus saline discrimination, or a cocaine versus procaine or saline discrimination, using a fixed ratio 20 schedule of food reinforcement. Cocaine, (+)-amphetamine and Dimethocaine all dose-dependently substituted for the training dose of cocaine (10 mg/kg) in both procedures. While procaine and lidocaine showed partial substitution in the cocaine versus saline procedure, much less substitution occurred in the cocaine versus procaine or saline discrimination. These data demonstrate that it is possible to train rats to discriminate between cocaine and another local anesthetic procaine, resulting in an increased pharmacological specificity of cocaine discrimination. The fact that Dimethocaine fully substituted for cocaine in both procedures indicates that this local anesthetic has more cocaine-like effects than others so far tested, which is consistent with results from other behavioral and neurochemical studies with this compound.