Tropacocaine

CAS# 537-26-8

Tropacocaine

2D Structure

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Tropacocaine

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Chemical Properties of Tropacocaine

Cas No. 537-26-8 SDF Download SDF
PubChem ID 10834 Appearance Powder
Formula C15H19NO2 M.Wt 245.32
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms Benzoyltropein; Tropacocain; TROPACOCAINE; Benzoyltropine; O-Benzoyltropine; Benzoylpseudotropeine;16052-34-9;19145-60-9
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (8-methyl-8-azabicyclo[3.2.1]octan-3-yl) benzoate
SMILES CN1C2CCC1CC(C2)OC(=O)C3=CC=CC=C3
Standard InChIKey XQJMXPAEFMWDOZ-UHFFFAOYSA-N
Standard InChI InChI=1S/C15H19NO2/c1-16-12-7-8-13(16)10-14(9-12)18-15(17)11-5-3-2-4-6-11/h2-6,12-14H,7-10H2,1H3
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Tropacocaine

Description1. Tropacocaine inhibits norepinephrine uptake at the concentration of 30 microM. 2. Tropacocaine can inhibit the spontaneous and veratridine-induced release of newly synthesized acetylcholine, but not via activation of presynaptic muscarinic receptors. 3. Tropacocaine can attenuate the oxotremorine-induced inhibition of the release of acetylcholine, suggesting antimuscarinic activity. 4. Tropacocaine has cardiovascular effects.
Targets5-HT Receptor | AChR

Tropacocaine Dilution Calculator

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Preparing Stock Solutions of Tropacocaine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.0763 mL 20.3815 mL 40.7631 mL 81.5262 mL 101.9077 mL
5 mM 0.8153 mL 4.0763 mL 8.1526 mL 16.3052 mL 20.3815 mL
10 mM 0.4076 mL 2.0382 mL 4.0763 mL 8.1526 mL 10.1908 mL
50 mM 0.0815 mL 0.4076 mL 0.8153 mL 1.6305 mL 2.0382 mL
100 mM 0.0408 mL 0.2038 mL 0.4076 mL 0.8153 mL 1.0191 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on Tropacocaine

Differential inhibition of synaptosomal accumulation of [3H]-monoamines by cocaine, tropacocaine and amphetamine in four inbred strains of mice.[Pubmed:2626447]

Pharmacol Biochem Behav. 1989 Sep;34(1):165-72.

The relative ability of cocaine, Tropacocaine and amphetamine to inhibit the uptake of [3H]norepinephrine (NE), [3H]dopamine (DA) and [3H]5-hydroxytryptamine (5HT) was examined in whole brain synaptosomes from BALB, C3H, C57BL and DBA inbred mouse strains. With inhibition of [3H]NE uptake, synaptosomes from BALB and C57 mice were substantially more sensitive to cocaine inhibition than those from DBA or C3H. Moreover, with BALB and C57 tissue, amphetamine was as potent as cocaine, whereas with C3H and DBA, amphetamine and Tropacocaine were much less potent inhibitors of [3H]NE uptake. With respect to [3H]DA accumulation, synaptosomes from BALB, C57 and DBA were equally sensitive to cocaine inhibition, while C3H synaptosomes were significantly less sensitive. In each of the four strains, amphetamine was more potent than cocaine, and Tropacocaine far less potent. The relative potencies of the three drugs varied significantly among the four strains. With [3H]5HT accumulation, synaptosomes from DBA were exquisitely sensitive to cocaine inhibition, followed by BALB and lastly by C57 and C3H. In each of these strains, amphetamine and Tropacocaine were equipotent at [3H]5HT inhibition, and less potent than cocaine. The results suggest that there are pronounced genetic differences in sensitivity to monoamine uptake inhibition by cocaine, which may arise from genetic differences in either carrier topology or other site of cocaine interaction. The results further suggest that genetic behavioral differences to cocaine and amphetamine may involve complex neurotransmitter interactions.

Cardiovascular effects of tropacocaine in conscious and anesthetized rabbits: lack of evidence for neuro-cardiac interactions and acute neurotoxicity.[Pubmed:7603635]

Neurotoxicology. 1995 Spring;16(1):145-51.

The cardiovascular effects of Tropacocaine, a structural analog of cocaine, were investigated in both conscious and anesthetized New Zealand white rabbits to determine if such effects were mediated through the CNS as had been demonstrated with cocaine, i.e., did a neuro-cardiac pathway exist? To facilitate the requisite cardiovascular measurements in both urethane- and pentobarbital-anesthetized animals, the right femoral artery and vein were cannulated for the measurement of arterial blood pressure and subsequent delivery of drugs, respectively. In addition, urethane-anesthetized animals had a branch of the left renal nerve isolated and multiunit renal nerve activity was monitored to obtain measures of sympathetic nerve activity originating from the CNS. Animals utilized in conscious experiments were surgically prepared 3 days prior to drug administration by placing canulae in the femoral artery and vein that were tunneled subcutaneously to the back between the scapulae. ECG and respiratory activity were also monitored in each animal. Doses of 0.3, 1, 3, and 10 mg/kg of Tropacocaine were administered in both an ascending and descending fashion at 15 min intervals to 5 animals in each group, i.e., conscious, urethane-, and pentobarbital-anesthetized. In urethane-anesthetized animals a comparison was made between sympathetic renal nerve activity, systolic and diastolic blood pressure, respiratory rate, and heart rate. No pressor effects were observed and the changes in renal nerve activity could not be assigned as the cause of the observed depressor effects at the higher doses.(ABSTRACT TRUNCATED AT 250 WORDS)

Determination and in-depth chromatographic analyses of alkaloids in South American and greenhouse-cultivated coca leaves.[Pubmed:8118557]

J Chromatogr A. 1994 Jan 21;659(1):163-75.

Methodology is described for the detection and/or determination of cocaine and minor alkaloids in South American coca as well as in greenhouse- and tropical-cultivated field coca of known taxonomy. Coca leaf from Bolivia, Peru, Ecuador and Colombia were subjected to the determination of cocaine, cis- and trans-cinnamoylcocaine, Tropacocaine, hygrine, cuscohygrine and the isomeric truxillines. The greenhouse samples were cocaine-bearing leaves of the genus Erythroxylum and included E. coca var. coca, E. novogranatense var. novogranatense and E. novogranatense var. truxillense, and the alkaloids determined were cocaine, ecgonine methyl ester, cuscohygrine, Tropacocaine and the cinnamoylcocaines. The tropical-cultivated coca were E. novogranatense var. novogranatense and E. coca var. coca. Cocaine and minor alkaloids were isolated from basified powdered leaf samples using a toluene extractant, followed by acid-Celite column chromatography. The isolated alkaloids were determined by capillary gas chromatography with flame ionization or electron-capture detection. Methodology is also presented for the isolation and mass spectral analysis of numerous trace-level coca alkaloids of unknown structure.

Effects of benzoyltropine and tropacocaine on several cholinergic processes in the rat brain.[Pubmed:1974643]

J Pharmacol Exp Ther. 1990 Aug;254(2):584-90.

Benzoyltropine and Tropacocaine are two contaminants of street-cocaine reported to have parasympatholytic activity. Because the mechanism underlying this activity is obscure, we investigated the effects of these compounds on several cholinergic processes: sodium-dependent choline uptake, sodium-independent choline uptake, acetylcholine synthesis, acetylcholine release (spontaneous and veratridine-induced) and binding of [3H]quinuclidinyl benzylate to muscarinic receptors. These studies used rat cerebral cortical synaptosomes, except for the receptor-binding studies, which used whole brain plasma membranes. Benzoyltropine and Tropacocaine each inhibited sodium-dependent choline uptake and acetylcholine synthesis in a dose-related manner that was competitive with extracellular choline. Benzoyltropine was 4 to 5 times more potent in both actions than Tropacocaine. Sodium-independent choline uptake was not affected by either compound. Benzoyltropine (30 microM) had no effect on the sodium-dependent uptake of norepinephrine, gamma-amino-butyric acid, glutamate or serotonin; Tropacocaine (30 microM) inhibited only norepinephrine uptake at this concentration. Benzoyltropine and Tropacocaine each inhibited the spontaneous and veratridine-induced release of newly synthesized acetylcholine, but not via activation of presynaptic muscarinic receptors. Instead, each compound was able to attenuate the oxotremorine-induced inhibition of the release of acetylcholine, suggesting antimuscarinic activity. Binding experiments showed that benzoyltropine and Tropacocaine were, respectively, about 1,000- and 10,000-fold less potent than scopolamine as receptor antagonists. Finally, we demonstrated that benzoyltropine accumulates in the rat brain after its peripheral injection (10 mg/kg i.p.) and remains there with a half-life similar to that of cocaine.(ABSTRACT TRUNCATED AT 250 WORDS)

Keywords:

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