(+)-Mesembrine - CAS 468-53-1
Molecular Formula:
C17H23NO3
Molecular Weight:
289.375
COA:
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Description:
Mesembrine is an alkaloid present in Sceletium tortuosum (kanna).
Purity:
95%
Synonyms:
(3aR,7aR)-3a-(3,4-dimethoxyphenyl)-1-methyloctahydro-6h-indol-6-one
MSDS:
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Density:
1.133 g/cm3
InChIKey:
DAHIQPJTGIHDGO-IAGOWNOFSA-N
InChI:
InChI=1S/C17H23NO3/c1-18-9-8-17(7-6-13(19)11-16(17)18)12-4-5-14(20-2)15(10-12)21-3/h4-5,10,16H,6-9,11H2,1-3H3/t16-,17-/m1/s1
Canonical SMILES:
CN1CCC2(C1CC(=O)CC2)C3=CC(=C(C=C3)OC)OC
1.Effects of Sceletium tortuosum in rats.
Loria MJ1, Ali Z2, Abe N2, Sufka KJ3, Khan IA2. J Ethnopharmacol. 2014 Aug 8;155(1):731-5. doi: 10.1016/j.jep.2014.06.007. Epub 2014 Jun 12.
ETHNOPHARMACOLOGICAL RELEVANCE: Broad historical and current uses in addition to diverse activity on CNS targets may make Sceletium tortuosum a useful therapeutic in a variety of clinical settings. This study sought to more broadly characterize activity of Sceletium tortuosum and mesembrine in a number of common, rodent-based assays that model nociception, depression, anxiety, ataxia, and abuse liability.
2.Medicinal use of Sceletium: Characterization of Phytochemical Components of Sceletium Plant Species using HPLC with UV and Electrospray Ionization--Tandem Mass Spectroscopy.
Patnala S1, Kanfer I. J Pharm Pharm Sci. 2015;18(4):414-23.
PURPOSE: Sceletium plants have been used for its medicinal properties for centuries. However, there is a wide range of Sceletium plant species in which various alkaloidal components such as ∆7mesembrenone, mesembrenol, mesembranol, mesembrenone, mesembrine hydrochloride, epimesembranol and, sceletium A4 differ between species. Hence, to ensure the quality of Sceletium products used as a medicine, it is imperative to identify the appropriate species using both botanical and chemical methods. The chemical approach to identify and characterize the phytochemical composition of a particular species facilitates the choice of species that will provide the purported therapeutic outcome. Hence, specific analytical methods to identify relevant constituents from complex matrices are necessary. Although HPLC-UV detection is commonly used to identify and estimate phytochemical content of medicinal plants, use of mass spectroscopy (MS) and tandem mass spectroscopy (MS/MS) can unequivocally confirm their presence/absence based on characteristic ions and fragmentation patterns.
3.A toxicological safety assessment of a standardized extract of Sceletium tortuosum (Zembrin®) in rats.
Murbach TS1, Hirka G2, Szakonyiné IP2, Gericke N3, Endres JR4. Food Chem Toxicol. 2014 Dec;74:190-9. doi: 10.1016/j.fct.2014.09.017. Epub 2014 Oct 6.
A well-characterized standardized hydroethanolic extract of a traditionally recognized mak (mild) variety of Sceletium tortuosum, a South African plant with a long history of traditional ingestion, is marketed under the trade name Zembrin(®) as an ingredient for use in functional foods and dietary supplements. It is standardized to contain 0.35-0.45% total alkaloids (mesembrenone and mesembrenol ≥60%, and mesembrine <20%). A 14-day repeated oral toxicity study was conducted at 0, 250, 750, 2500, and 5000 mg/kg bw/day. A 90-day subchronic repeated oral toxicity study was conducted at 0, 100, 300, 450, and 600 mg/kg bw/day. Because S. tortuosum has a long history of human use for relieving stress and calming, a functional observation battery, including spontaneous locomotor activity measured using LabMaster ActiMot light-beam frames system, was employed. Several parameters, such as locomotion, rearing behavior, spatial parameters, and turning behavior were investigated in the final week of the study.
4.Pyrone Diels-Alder Routes to Indolines and Hydroindolines: Syntheses of Gracilamine, Mesembrine, and Δ(7) -Mesembrenone.
Gan P1, Smith MW2,1, Braffman NR2, Snyder SA3,4,5. Angew Chem Int Ed Engl. 2016 Mar 7;55(11):3625-30. doi: 10.1002/anie.201510520. Epub 2016 Feb 10.
Although the Diels-Alder reaction has long been utilized for the preparation of numerous heterocycles, opportunities to extend its power remain. Herein, we detail a simple, modular, and robust approach that combines various amines regioselectively with 4,6-dichloropyrone to create substrates which, under appropriate conditions, can directly deliver varied indolines and hydroindolines through [4+2] cycloadditions with substitution patterns difficult to access otherwise. As an initial demonstration of the power of the strategy, several different natural products have been obtained either formally or by direct total synthesis, with efforts toward one of these-the complex amaryllidaceae alkaloid gracilamine-affording the shortest route to date in terms of linear step count.
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