Tropine
(Synonyms: 托品醇) 目录号 : GC45092
A natural tropane alkaloid
Cas No.:120-29-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Tropine is a naturally-occurring tropane alkaloid extracted primarily from plants of the Solanaceae family. It serves as an intermediate in the synthesis of a variety of bioactive alkaloids, including atropine , benztropine , and scopolamine, many of which have potent neurological actions.
| Cas No. | 120-29-6 | SDF | |
| 别名 | 托品醇 | ||
| Canonical SMILES | O[C@H]1C[C@@H](CC2)N(C)[C@@H]2C1 | ||
| 分子式 | C8H15NO | 分子量 | 141.2 |
| 溶解度 | DMF: 30 mg/ml,DMSO: 30 mg/ml,Ethanol: 30 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 | 7.0822 mL | 35.4108 mL | 70.8215 mL |
| 5 mM | 1.4164 mL | 7.0822 mL | 14.1643 mL |
| 10 mM | 0.7082 mL | 3.5411 mL | 7.0822 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。
Synthesis of Tropine-Based Functionalized Acidic Ionic Liquids and Catalysis of Esterification
Int J Mol Sci 2022 Oct 25;23(21):12877.PMID:36361664DOI:10.3390/ijms232112877.
Some traditional acidic ionic liquids (AILs) have shown great catalytic potential in esterification; meanwhile, the design and application of more new AILs are expected at present.Tropine-based functionalized acidic ionic liquids (FAILs) were synthesized to realize esterification catalysis for the first time; with aspirin synthesis as the template reaction, key influences on the substrate conversion and product yield of the synthesis, such as IL type, ratio of salicylic acid to acetic anhydride, temperature, reaction time and amount of IL, were investigated. The new tropine-based FAILs exhibited excellent performance in catalytic synthesis of aspirin with 88.7% yield and 90.8% selectivity. Multiple recovery and re-usage of N-(3-propanesulfonic acid) Tropine is the cation, and p-toluenesulfonic acid is the anion. ([Trps][OTs]) shows satisfactory results. When [Trps][OTs] was used to catalyze different esterification reactions, it also showed good results. The above studies proved that ionic liquid [Trps][OTs] could serve as an ideal green solvent for esterification reaction, which serves as a suitable substitute for current catalysts.
De Novo Production of the Plant-Derived Tropine and Pseudotropine in Yeast
ACS Synth Biol 2019 Jun 21;8(6):1257-1262.PMID:31181154DOI:10.1021/acssynbio.9b00152.
Tropine and pseudotropine with opposite stereospecific configurations as platform compounds are central building blocks in both biosynthesis and chemical synthesis of pharmacologically important tropane and nortropane alkaloids. The supply of plant-derived Tropine and pseudotropine still heavily depends on either plant extraction or chemical synthesis. Advances in synthetic biology prompt the microbial synthesis of various valuable chemicals. With the biosynthetic pathway elucidation of Tropine and pseudotropine in several Solanaceae plants, the key genes were sequentially identified. Here, the enzymes responsible for converting N-methylpyrrolinium into Tropine and pseudotropine from Anisodus acutangulus were characterized. Reconstruction of the six-step biosynthetic pathways into Saccharomyces cerevisiae provides cell chassis producing Tropine and pseudotropine with 0.13 and 0.08 mg/L titers from simple feedstocks in a shake flask, respectively. The strains described not only offer alternative sources of these central intermediates and their derived alkaloids but also provide platforms for pathway enzyme discovery.
Structure-activity relationships among derivatives of dicarboxylic acid esters of Tropine
Pharmacol Ther 2002 Oct;96(1):1-21.PMID:12441175DOI:10.1016/s0163-7258(02)00296-6.
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.
Tropine dehydrogenase: purification, some properties and an evaluation of its role in the bacterial metabolism of Tropine
Biochem J 1995 Apr 15;307 ( Pt 2)(Pt 2):603-8.PMID:7733902DOI:10.1042/bj3070603.
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.
Functional characterisation of a tropine-forming reductase gene from Brugmansia arborea, a woody plant species producing tropane alkaloids
Phytochemistry 2016 Jul;127:12-22.PMID:26988730DOI:10.1016/j.phytochem.2016.03.008.
Brugmansia arborea is a woody plant species that produces tropane alkaloids (TAs). The gene encoding tropine-forming reductase or tropinone reductase I (BaTRI) in this plant species was functionally characterised. The full-length cDNA of BaTRI encoded a 272-amino-acid polypeptide that was highly similar to tropinone reductase I from TAs-producing herbal plant species. The purified 29kDa recombinant BaTRI exhibited maximum reduction activity at pH 6.8-8.0 when tropinone was used as substrate; it also exhibited maximum oxidation activity at pH 9.6 when Tropine was used as substrate. The Km, Vmax and Kcat values of BaTRI for tropinone were 2.65mM, 88.3nkatmg(-1) and 2.93S(-1), respectively, at pH 6.4; the Km, Vmax and Kcat values of TRI from Datura stramonium (DsTRI) for tropinone were respectively 4.18mM, 81.20nkatmg(-1) and 2.40S(-1) at pH 6.4. At pH 6.4, 6.8 and 7.0, BaTRI had a significantly higher activity than DsTRI. Analogues of tropinone, 4-methylcyclohexanone and 3-quinuclidinone hydrochloride, were also used to investigate the enzymatic kinetics of BaTRI. The Km, Vmax and Kcat values of BaTRI for Tropine were 0.56mM, 171.62nkat.mg(-1) and 5.69S(-1), respectively, at pH 9.6; the Km, Vmax and Kcat values of DsTRI for Tropine were 0.34mM, 111.90nkatmg(-1) and 3.30S(-1), respectively, at pH 9.6. The tissue profiles of BaTRI differed from those in TAs-producing herbal plant species. BaTRI was expressed in all examined organs but was most abundant in secondary roots. Finally, tropane alkaloids, including hyoscyamine, anisodamine and scopolamine, were detected in various organs of B. arborea by HPLC. Interestingly, scopolamine constituted most of the tropane alkaloids content in B. arborea, which suggests that B. arborea is a scopolamine-rich plant species. The scopolamine content was much higher in the leaves and stems than in other organs. The gene expression and TAs accumulation suggest that the biosynthesis of hyoscyamine, especially scopolamine, occurred not only in the roots but also in the aerial parts of B. arborea.