Pseudotropine

CAS# 135-97-7

Pseudotropine

2D Structure

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  • Tropine

    Catalog No.:BCN0350
    CAS No.:120-29-6

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Pseudotropine

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Chemical Properties of Pseudotropine

Cas No. 135-97-7 SDF Download SDF
PubChem ID 8424 Appearance White to yellowish crystals
Formula C8H15NO M.Wt 141.21
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms 120-29-6;Tropine
Solubility Soluble in water
Chemical Name 8-methyl-8-azabicyclo[3.2.1]octan-3-ol
SMILES CN1C2CCC1CC(C2)O
Standard InChIKey CYHOMWAPJJPNMW-UHFFFAOYSA-N
Standard InChI InChI=1S/C8H15NO/c1-9-6-2-3-7(9)5-8(10)4-6/h6-8,10H,2-5H2,1H3
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.

Source of Pseudotropine

The roots of Atropa belladonna

Biological Activity of Pseudotropine

DescriptionPseudotropine can cause hepatic necrosis and gastritis with ulceration or erosions.
In vivo

Toxicity of field bindweed (Convolvulus arvensis) to mice.[Pubmed: 8592835]

Vet. Hum. Toxicol., 1995, 37(5):452-4

The effects of feeding high and low doses of field bindweed (Convolvulus arvensis) to mice were investigated. Bindweed contains several alkaloids, including Pseudotropine, and lesser amounts of tropine, tropinone, and meso-cuscohygrine.
METHODS AND RESULTS:
Mice fed bindweed exclusively died or were euthanized after 4-7 d and had severe hepatic necrosis and gastritis with ulceration or erosions. Mice fed low doses of bindweed along with standard laboratory mouse diet for 6 or 8 w had no clinical disease or gross lesions on necropsy examination but did have histologic lesions of mild multifocal hepatitis and gastritis.

Protocol of Pseudotropine

Structure Identification
Tetrahedron Letters Volume 25, Issue 44, 1984, Pages 5091–5094

A new synthetic route to tropane alkaloids. Pseudotropine and tropacocaine[Reference: WebLink]

Pseudotropine and tropacocaine have been synthesized by a facile route involving the [4 + 2] nitroso cycloaddition followed by internal SN2 displacement.

Pseudotropine Dilution Calculator

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Preparing Stock Solutions of Pseudotropine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 7.0817 mL 35.4083 mL 70.8165 mL 141.633 mL 177.0413 mL
5 mM 1.4163 mL 7.0817 mL 14.1633 mL 28.3266 mL 35.4083 mL
10 mM 0.7082 mL 3.5408 mL 7.0817 mL 14.1633 mL 17.7041 mL
50 mM 0.1416 mL 0.7082 mL 1.4163 mL 2.8327 mL 3.5408 mL
100 mM 0.0708 mL 0.3541 mL 0.7082 mL 1.4163 mL 1.7704 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 Pseudotropine

Tropine forming tropinone reductase gene from Withania somnifera (Ashwagandha): biochemical characteristics of the recombinant enzyme and novel physiological overtones of tissue-wide gene expression patterns.[Pubmed:24086372]

PLoS One. 2013 Sep 25;8(9):e74777.

Withania somnifera is one of the most reputed medicinal plants of Indian systems of medicine synthesizing diverse types of secondary metabolites such as withanolides, alkaloids, withanamides etc. Present study comprises cloning and E. coli over-expression of a tropinone reductase gene (WsTR-I) from W. somnifera, and elucidation of biochemical characteristics and physiological role of tropinone reductase enzyme in tropane alkaloid biosynthesis in aerial tissues of the plant. The recombinant enzyme was demonstrated to catalyze NADPH-dependent tropinone to tropine conversion step in tropane metabolism, through TLC, GC and GC-MS-MS analyses of the reaction product. The functionally active homodimeric ~60 kDa enzyme catalyzed the reaction in reversible manner at optimum pH 6.7. Catalytic kinetics of the enzyme favoured its forward reaction (tropine formation). Comparative 3-D models of landscape of the enzyme active site contours and tropinone binding site were also developed. Tissue-wide and ontogenic stage-wise assessment of WsTR-I transcript levels revealed constitutive expression of the gene with relatively lower abundance in berries and young leaves. The tissue profiles of WsTR-I expression matched those of tropine levels. The data suggest that, in W. somnifera, aerial tissues as well possess tropane alkaloid biosynthetic competence. In vivo feeding of U-[(14)C]-sucrose to orphan shoot (twigs) and [(14)C]-chasing revealed substantial radiolabel incorporation in tropinone and tropine, confirming the de novo synthesizing ability of the aerial tissues. This inherent independent ability heralds a conceptual novelty in the backdrop of classical view that these tissues acquire the alkaloids through transportation from roots rather than synthesis. The TR-I gene expression was found to be up-regulated on exposure to signal molecules (methyl jasmonate and salicylic acid) and on mechanical injury. The enzyme's catalytic and structural properties as well as gene expression profiles are discussed with respect to their physiological overtones.

Toxicity of field bindweed (Convolvulus arvensis) to mice.[Pubmed:8592835]

Vet Hum Toxicol. 1995 Oct;37(5):452-4.

The effects of feeding high and low doses of field bindweed (Convolvulus arvensis) to mice were investigated. Bindweed contains several alkaloids, including Pseudotropine, and lesser amounts of tropine, tropinone, and meso-cuscohygrine. Mice fed bindweed exclusively died or were euthanized after 4-7 d and had severe hepatic necrosis and gastritis with ulceration or erosions. Mice fed low doses of bindweed along with standard laboratory mouse diet for 6 or 8 w had no clinical disease or gross lesions on necropsy examination but did have histologic lesions of mild multifocal hepatitis and gastritis.

Tropine dehydrogenase: purification, some properties and an evaluation of its role in the bacterial metabolism of tropine.[Pubmed:7733902]

Biochem J. 1995 Apr 15;307 ( Pt 2):603-8.

Tropine dehydrogenase was induced by growth of Pseudomonas AT3 on atropine, tropine or tropinone. It was NADP(+)-dependent and gave no activity with NAD+. The enzyme was very unstable but a rapid purification procedure using affinity chromatography that gave highly purified enzyme was developed. The enzyme gave a single band on isoelectric focusing with an isoelectric point at approximately pH 4. The native enzyme had an M(r) of 58,000 by gel filtration and 28,000 by SDS/PAGE and therefore consists of two subunits of equal size. The enzyme displayed a narrow range of specificity and was active with tropine and nortropine but not with Pseudotropine, pseudonortropine, or a number of related compounds. The apparent Kms were 6.06 microM for tropine and 73.4 microM for nortropine with the specificity constant (Vmax/Km) for tropine 7.8 times that for Pseudotropine. The apparent Km for NADP+ was 48 microM. The deuterium of [3-2H]tropine and [3-2H]Pseudotropine was retained when these compounds were converted into 6-hydroxycyclohepta-1,4-dione, an intermediate in tropine catabolism, showing that the tropine dehydrogenase, although induced by growth on tropine, is not involved in the catabolic pathway for this compound. 6-Hydroxycyclohepta-1,4-dione was also implicated as an intermediate in the pathways for Pseudotropine and tropinone catabolism.

Structure-activity relationships among derivatives of dicarboxylic acid esters of tropine.[Pubmed:12441175]

Pharmacol Ther. 2002 Oct;96(1):1-21.

Several categories of neuromuscular blocking bisquaternary tropine and tropane derivatives were synthesized and studied in the past five decades, mainly with the purpose of arriving at meaningful information about structure-activity relationships. Such a structure-activity relationship database is important in the development of new muscle relaxants with improved pharmacological characteristics. Although quaternary tropine diesters were explored since 1952, most of them were developed in the last decade. Over 250 such agents are being reviewed here. The skeleton of the majority of them consists of two tropines, connected through their 3-OH group with various dicarboxylic acid ester linkages and quaternized by several mostly di- and trisubstituted benzyl groups. The significance of changing the quaternizing group; the diester linker; and, to a smaller extent, the substituents and their steric orientation on the tropane ring and some alterations of the tropane ring itself have been explored in in vivo experiments on anesthetized rats. Di- or trisubstituted alkoxy and/or acyloxybenzyl quaternaries of certain tropinyl diesters, e.g., glutaryl, fumaryl, and cyclobutane-1,2-dicarboxylyl, showed an optimal profile with respect to desirable neuromuscular blocking actions and side effects, which was confirmed on other experimental animal species. The details of the structural changes toward obtaining new ultrashort-acting nondepolarizing muscle relaxants are discussed.

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