Mesembrine
(Synonyms: 松叶菊碱,(+)-Mesembrine) 目录号 : GC48814An alkaloid with 5-HT reuptake inhibitory activity
Cas No.:24880-43-1
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
Mesembrine is an alkaloid that has been found in S. tortuosum and has serotonin (5-HT) reuptake inhibitory activity.1 It selectively binds to the 5-HT transporter (SERT; IC50 = 4.3 µg/ml) over a variety of receptors (IC50s = 148->750 µg/ml).2 Mesembrine inhibits the reuptake of 5-HT in vitro (Ki = 1.4 nM). It has analgesic effects in the hot plate test when administered at a dose of 20 mg/kg but does not induce a preference in the conditioned place preference test (CPP).2,3
1.Krstenansky, J.L.Mesembrine alkaloids: Review of their occurrence, chemistry, and pharmacologyJ. Ethnopharmacol.19510-19(2017) 2.Harvey, A.L., Young, L.C., Viljoen, A.M., et al.Pharmacological actions of the South African medicinal and functional food plant Sceletium tortuosum and its principal alkaloidsJ. Ethnopharmacol.137(3)1124-1129(2011) 3.Loria, M.J., Ali, Z., Abe, N., et al.Effects of Sceletium tortuosum in ratsJ. Ethnopharmacol.155(1)731-735(2014)
| Cas No. | 24880-43-1 | SDF | |
| 别名 | 松叶菊碱,(+)-Mesembrine | ||
| Canonical SMILES | COC1=CC=C([C@]2(CCN3C)[C@]3([H])CC(CC2)=O)C=C1OC | ||
| 分子式 | C17H23NO3 | 分子量 | 289.4 |
| 溶解度 | Chloroform: 10 mg/ml,Ethanol: 10 mg/ml | 储存条件 | -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 | 3.4554 mL | 17.2771 mL | 34.5543 mL |
| 5 mM | 0.6911 mL | 3.4554 mL | 6.9109 mL |
| 10 mM | 0.3455 mL | 1.7277 mL | 3.4554 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。
Mesembrine: The archetypal psycho-active Sceletium alkaloid
Phytochemistry 2019 Oct;166:112061.PMID:31299396DOI:10.1016/j.phytochem.2019.112061.
(-)-Mesembrine is a chiral alkaloid that features an aryloctahydroindole skeleton and is most commonly found in species of the succulent genus Sceletium. Several Sceletium species are used by various ethnic groups in South Africa to manage disorders of the central nervous system. Binding assays have revealed that Mesembrine is a more potent inhibitor of the serotonin transporter (SERT) than fluoxetine (Prozac) which has prompted the commercialization of mesembrine-containing consumer products. The congested all carbon quaternary stereocenter present at the bridgehead of Mesembrine has rendered it a compound of interest for research in synthetic chemistry, which has assisted in the absolute configuration of the naturally occurring isomer to be assigned. Accordingly, this review will cover the recent literature pertaining to the distribution, structural elucidation, chemotaxonomy, biosynthesis, organic synthesis, as well as the biological activities of (-)-mesembrine. Recent synthetic procedures of the non-natural enantiomer as well as the racemate are also considered.
Mesembrine alkaloids: Review of their occurrence, chemistry, and pharmacology
J Ethnopharmacol 2017 Jan 4;195:10-19.PMID:27939420DOI:10.1016/j.jep.2016.12.004.
Ethnopharmacological relevance: Mesembrine alkaloids are considered to be the primary active constituents of the South African medicinal plant Sceletium tortuosum (L.) N.E.Br. (Aizoaceae), and it is used as the dried or fermented aerial material from the plant, which is known as kanna (aka, channa, kougoed). Traditional regional use ranged from relieving thirst, mild analgesia, and alteration of mood. Current interest has focused primarily on the antidepressant action of preparations based on the plant and commercialization is expanding the recognition and availability of these preparations. Materials and methods: Searches for the keywords "Sceletium or Mesembrine" were performed in "PubMed-NCBI", "Chemical Abstracts SciFinder" and "Thomson Reuters Web of Science" databases in addition to the inclusion of references cited within prior reviews and scientific reports. Additionally the "SciFinder" database was searched using 3a-phenyl-cis-octahydroindole in the SciFinder Substructure Module (SSM). Plant taxonomy was validated by the database "The Plant List". Results: This review focuses on the chemistry, analysis, and pharmacology of the Mesembrine alkaloids. Despite a long history of medicinal used and research investigation, there has been a renewed interest in the pharmacological properties of the Mesembrine alkaloids and much of the pharmacology has only recently been published. The two major active alkaloids Mesembrine and mesembrenone are still in the process of being more fully characterized pharmacologically. They are serotonin reuptake inhibitors, which provides a rationale for the plant's traditional use as an antidepressant, but other actions are beginning to appear in the literature. Additionally, mesembrenone has reasonably potent PDE4 inhibitory activity. This review intends to provide an overview of the available literature, summarize the current findings, and put them in perspective with earlier studies and reviews.
A Concise Total Synthesis of (-)-Mesembrine
J Org Chem 2016 Nov 4;81(21):10165-10171.PMID:27723969DOI:10.1021/acs.joc.6b01908.
A concise total synthesis of Mesembrine (four steps from known compound) was achieved both racemically and asymmetrically. Two key reactions were used here. One is the Rh(I)-catalyzed [5 + 1] cycloaddition of vinylcyclopropane 3c and CO. The other one is Buchwald's Pd-catalyzed coupling reaction that coupled β,γ-cyclohexenone 2c with aryl bromide 5 (using dppe ligand for racemic or (S)-Antphos ligand for asymmetric synthesis) to give γ,γ-disubstituted α,β-cyclohexenone 1c. Finally, aza-Michael addition converted 1c to Mesembrine.
Quantification of Mesembrine and mesembrenone in mouse plasma using UHPLC-QToF-MS: Application to a pharmacokinetic study
Biomed Chromatogr 2017 Mar;31(3).PMID:27526669DOI:10.1002/bmc.3815.
Sceletium tortuosum, is an indigenous herb of South Africa which is widely used as an herbal supplement in the treatment of anxiety and stress. Mesembrenone and Mesembrine are the two main pharmacologically active alkaloids present in the extract. Despite the wide therapeutic applications of Sceletium extract, there are no reports of in vivo pharmacokinetic properties or analytical methods to quantify these two important alkaloids in plasma. Therefore, the current study aimed to develop and validate a simple and sensitive analytical method for simultaneous quantification of mesembrenone and Mesembrine in mouse plasma. Ultra-high-performance liquid chromatography-mass spectrometry (UHPLC/QToF-MS) was employed to achieve our objectives. The compounds were extracted using protein precipitation by methanol (100%) with quinine as an internal standard. The lower limit of quantification for both the compounds was 10 ng/mL. The extraction recovery was between 87 and 93% for both compounds with no matrix effects on the analysis. The accuracy was between 89.5 and 106% and precision was <12.6% for all quality control samples. This validated method was successfully applied to evaluate the i.v. plasma pharmacokinetics of Mesembrine and mesembrenone in mouse. However, the oral bioavailability of these alkaloids was poor and the plasma levels were below the detection limits.
HPLC analysis of mesembrine-type alkaloids in Sceletium plant material used as an African traditional medicine
J Pharm Pharm Sci 2010;13(4):558-70.PMID:21486531DOI:10.18433/j3dk5f.
Purpose: Sceletium plant species have been reported to contain psychoactive alkaloids, specifically belonging to mesembrine-type alkaloids. Sceletium is presently marketed through health shops and on the internet as dried plant powder and as pharmaceutical dosage forms and purported to be useful in the treatment of psychological disorders. However, there are no validated analytical methods and reference standards of the relevant alkaloids are not commercially available for use in the analysis and quality control of Sceletium products and dosage forms. Hence, the objective of this research was to isolate and characterize appropriate analytical markers for use in the assay and as well as markers for fingerprinting by high performance liquid chromatography (HPLC). Methods: The separation of the relevant alkaloids was carried out on a C18 column and detected at a UV wavelength of 228 nm. The method was validated and used to assay the mesembrine-type alkaloids namely Δ(7)mesembrenone, mesembranol, mesembrenone, Mesembrine and epimesembranol. Results: The calibration curves were found to be linear over the entire concentration range of 400-60,000 ng/ml with correlation coefficients >0.99. The accuracies of the relevant alkaloids were found to be between 94.8 and 103.6% with an inter-day relative standard deviation (RSD) of less than 2.8%. The precision studies showed inter-day RSD's of less than 3%. The recoveries were all within the range of 95 and 105% (RSD <4.5%) and the limits of quantitation (LOQ) and detection (LOD) were found to be 100 and 200 ng/ml respectively using the respective S/N ratios of 3 and 10. Conclusions. An HPLC method for the quantitative analysis of Δ(7)mesembrenone, mesembranol, mesembrenone, Mesembrine and epimesembranol in Sceletium plant material has been developed and validated. This assay method can be applied for the quality control of Sceletium plant material which is used as an African Traditional Medicine for the treatment of psychological disorders.