Buy Mesembrine (Sceletium) Cas 468-53-1

Buy Mesembrine (Sceletium) Cas 468-53-1

Mesembrine is an alkaloid primarily derived from the plant Sceletium tortuosum, commonly known as kanna. This compound is noted for its psychoactive properties, particularly as a serotonin reuptake inhibitor, which contributes to its potential use in treating mood disorders and anxiety. Mesembrine has garnered interest in both traditional medicine and modern pharmacology, where it is explored for its effects on enhancing mood and cognitive function.

Kanna itself has a long history of use by indigenous peoples in Southern Africa, who utilized it for its mood-enhancing and stress-relieving effects, often consuming it in various forms such as teas or chews.^[1][2][3][4]

Mesembrine has also been identified in Mesembryanthemum cordifolium, Delosperma echinatum, and Oscularia deltoides.^[5]

Mesembrine has been shown to act as a serotonin reuptake inhibitor (K_i = 1.4 nM), and has also been found to behave as a weak inhibitor of the enzyme phosphodiesterase 4 (PDE4) (K_i = 7,800 nM).^[6] A concentrated mesembrine extract of Sceletium tortuosum may exert antidepressant effects by acting as a monoamine releasing agent.^[7] As such, mesembrine likely plays a dominant role in the antidepressant effects of kanna.^[8]

Rat studies have evaluated effects of kanna extract, finding analgesic and antidepressant potential.^[9] No adverse results were noted for a commercial extract up to 5000 mg/kg daily in rats.

Buy Mesembrine (Sceletium) Cas 468-53-1

Buy Mesembrine (Sceletium) Cas 468-53-1

Buy Mesembrine (Sceletium) Cas 468-53-1

Buy Mesembrine (Sceletium) Cas 468-53-1

Buy Mesembrine (Sceletium) Cas 468-53-1

Buy Mesembrine (Sceletium) Cas 468-53-1

Buy Mesembrine (Sceletium) Cas 468-53-1

Buy Mesembrine (Sceletium) Cas 468-53-1

Buy Mesembrine (Sceletium) Cas 468-53-1

Mesembrine was first isolated and characterized in 1957.^[11] It is a tricyclic molecule with two bridgehead chiral carbons located between the five-membered and six-membered rings. The naturally occurring form of mesembrine produced by plants is the levorotatory isomer, (−)-mesembrine, where the carbon atoms at positions 3a and 7a both have the S configuration (3aS,7aS).

468-53-1

Chemical Structure

Mesembrine

Synonym(s): (+)-Mesembrine

• CAS No.:468-53-1
• Formula:C₁₇H₂₃NO₃
• Molecular Weight:289.37

IUPAC Name: (3aR,7aR)-3a-(3,4-dimethoxyphenyl)-1-methyloctahydro-6H-indol-6-one

InChIKey: DAHIQPJTGIHDGO-IAGOWNOFSA-N

SMILES: O=C1CC[C@]2(C3=CC=C(OC)C(OC)=C3)CCN(C)[C@]2([H])C1

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   • Appearance: Colorless to light yellow liquid
   • Density: 1.133±0.06 g/cm3 (Predicted)

   • Boiling point: 419.2±45.0 °C (Predicted)
   • Storage conditions: 20°C Freezer

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   Mesembrine is an alkaloid, [] a naturally occurring organic compound containing basic nitrogen atoms. It is primarily found in plants of the genus Sceletium, a group of succulents native to South Africa. [] The Sceletium genus is part of the Aizoaceae family. [] Mesembrine is particularly abundant in Sceletium tortuosum, a species traditionally used by the Khoisan people for various purposes. [, ] While several Sceletium species contain mesembrine, the emarcidum type generally lacks alkaloids. [] Mesembrine is a subject of significant scientific research due to its unique pharmacological properties. [, , ] It’s crucial to distinguish between different Sceletium species due to variations in alkaloid content. []

   Future Directions

   • Comprehensive Pharmacological Characterization: Further research is needed to fully elucidate mesembrine’s mechanisms of action, particularly its effects on various neurotransmitter systems and intracellular signaling pathways. [, ]
   • Clinical Studies: While preclinical studies suggest potential therapeutic benefits, well-designed clinical trials are crucial for evaluating the efficacy and safety of mesembrine in humans. [, ] These trials should focus on specific conditions, including anxiety, depression, and other potential applications.
   • Structure-Activity Relationship Studies: Synthesizing and evaluating mesembrine analogs can help identify structural features critical for its pharmacological activity. [, ] This knowledge can guide the development of more potent and selective therapeutic agents.
   • Bioavailability and Metabolism: Investigating mesembrine’s pharmacokinetic properties, including its absorption, distribution, metabolism, and excretion, is essential for optimizing its therapeutic use. [] Understanding its metabolic fate can help identify potential drug interactions and inform dosage regimens.
   • Toxicity Studies: Thorough toxicological assessments are necessary to determine the safety profile of mesembrine and identify potential adverse effects. [] Long-term safety studies are particularly important for evaluating its suitability as a chronic treatment option.

   Source and Classification

   Mesembrine is classified as an alkaloid, a group of naturally occurring organic compounds that mostly contain basic nitrogen atoms. It is primarily sourced from Sceletium tortuosum, a succulent plant native to southern Africa, where it has been traditionally used by indigenous peoples for its mood-enhancing effects. Other species that contain mesembrine include Mesembryanthemum cordifolium, Delosperma echinatum, and Oscularia deltoides   .

   Synthesis Analysis

   The synthesis of mesembrine has been a focal point of research due to its complex structure and biological activity. Over 40 total syntheses have been reported since the first synthesis by Shamma et al. in 1965, which involved a lengthy 21-step process. This route utilized key reactions such as the Diels-Alder reaction for constructing the six-membered ring and α-allylation for forming the quaternary carbon   .

   Recent advancements have led to more efficient syntheses, including a concise four-step synthesis reported by Wang et al., which employed Rhodium(I)-catalyzed cycloaddition and Palladium-catalyzed coupling reactions   . This method demonstrated yields of up to 76% for the final product after removing protective groups.

   Molecular Structure Analysis

   Mesembrine features a tricyclic structure characterized by an aryloctahydroindole skeleton. The naturally occurring form is the levorotatory isomer, (−)-mesembrine, with specific stereochemistry at its chiral centers (3aS,7aS)   . The compound’s complex structure includes a congested all-carbon quaternary stereocenter at the bridgehead, which poses unique challenges and opportunities for synthetic chemists  .

   Chemical Reactions Analysis

   Mesembrine participates in various chemical reactions, primarily as a serotonin transporter inhibitor with a binding affinity (K_i) of 1.4 nM, making it more potent than fluoxetine (Prozac). It also exhibits weak inhibition of phosphodiesterase 4 with a K_i of 7,800 nM   . These interactions underline its potential applications in pharmacology, particularly in managing mood disorders.

   Mechanism of Action

   The mechanism of action of mesembrine primarily involves its role as a serotonin reuptake inhibitor. By inhibiting the serotonin transporter, mesembrine increases serotonin levels in the synaptic cleft, which can enhance mood and alleviate symptoms of depression and anxiety   . Additionally, it may act as a monoamine releasing agent, contributing further to its antidepressant effects.

   Physical and Chemical Properties Analysis

   Mesembrine is characterized by several notable physical and chemical properties:

   • Molecular Formula: C1313​H1717​N
   • Molecular Weight: 201.29 g/mol
   • Melting Point: Specific data on melting point varies with purity but generally falls within standard ranges for similar compounds.
   • Solubility: Mesembrine is soluble in organic solvents but has limited solubility in water.

   These properties are essential for understanding its behavior in biological systems and during synthesis.

   Applications

   The applications of mesembrine extend across various fields:

   • Pharmacology: Due to its psychoactive properties, mesembrine is being explored as a treatment for mood disorders and anxiety.
   • Traditional Medicine: Indigenous cultures have utilized kanna for centuries for its stress-relieving effects.
   • Synthetic Chemistry: The complexity of mesembrine’s structure has made it a target for synthetic chemists interested in developing new methodologies for constructing quaternary stereocenters   .

   Introduction to Mesembrine: Historical Context and Significance

   Ethnobotanical Origins in Sceletium tortuosum and Related Species

   Sceletium tortuosum belongs to the Aizoaceae family, specifically the subfamily Mesembryanthemoideae. The genus Sceletium comprises eight recognized species, including S. crassicaule, S. emarcidum, S. exalatum, S. expansum, S. rigidum, S. strictum, S. tortuosum, and S. varians. These species are characterized by distinctive skeletonized leaf venation patterns visible upon drying—a feature that gives the genus its name (from the Latin “sceletus,” meaning skeleton) [1] [8]. Mesembrine-type alkaloids predominate in S. tortuosum, which typically contains 0.3–0.86% mesembrine by dry weight, alongside structurally related compounds including mesembrenone, mesembrenol, mesembranol, and tortuosamine [1] [2] [6]. Crucially, traditional preparation methods, particularly aerobic fermentation of crushed plant material, transform mesembrine into more bioactive forms like Δ7-mesembrenone while reducing potentially harmful oxalate content [1] [6]. This indigenous processing technique significantly enhances the material’s psychoactive properties and demonstrates sophisticated pre-scientific biochemical understanding.

   Table 1: Key Alkaloids in Sceletium tortuosum

   Alkaloid	Chemical Class	Relative Abundance	Notable Properties
   Mesembrine	Mesembrine-type	High (0.3-0.86%)	Potent serotonin reuptake inhibitor
   Mesembrenone	Mesembrine-type	Variable	PDE4 inhibition, SERT activity
   Mesembrenol	Mesembrine-type	Moderate	Contributes to overall activity
   Mesembranol	Mesembrine-type	Moderate	Contributes to overall activity
   Tortuosamine	Tortuosamine-type	Low	Structural uniqueness
   Sceletium A4	Sceletium A4-type	Trace	Minor contributor

   Historical Use in Indigenous South African Medicine

   The earliest documented use of Sceletium tortuosum dates to 1662, recorded by Dutch colonial administrator Jan van Riebeeck, who noted trade with indigenous Khoisan peoples involving sheep exchanged for ‘kanna’ material [1] [6]. However, archaeological and anthropological evidence strongly suggests millennia of prior use by San hunter-gatherers and Khoi pastoralists. These groups traditionally consumed fermented plant material as a masticatory (kougoed translates to “chewable thing” in Afrikaans), swallowing the saliva for its psychoactive effects [1] [6]. Beyond its mood-altering properties, indigenous applications encompassed relief from hunger and thirst during long hunts, reduction of anxiety and stress, treatment of toothache and abdominal pain, and use in prenatal care for nausea and post-partum recovery [1] [6]. Spiritual and social dimensions were equally significant, with Sceletium integrated into rituals and communal gatherings to facilitate trance states and enhance social bonding [6] [8]. This multifaceted use represents one of southern Africa’s most sophisticated and enduring ethnopharmacological traditions.

   Emergence in Modern Pharmacological Research

   Scientific interest in mesembrine began in the early 20th century. Hans Zwicky first reported alkaloids in Sceletium tortuosum in 1914, though initial structural assignments were incorrect [1] [4]. The definitive isolation and structural elucidation of (-)-mesembrine occurred in 1957 by Bodendorf and Krieger, marking the foundation of modern study [2] [4]. Research accelerated in the late 20th and early 21st centuries, driven by interest in its unique mechanism of action. The development of standardized extracts, most notably Zembrin® (a characterized ethanolic extract), facilitated preclinical and clinical investigations [3] [5] [9]. Patent filings in the 1990s and 2000s covering extraction methods and uses signaled its commercial potential [1]. Modern research focuses primarily on mesembrine’s dual affinity for the serotonin transporter (SERT) and phosphodiesterase-4 (PDE4) enzyme—targets critically implicated in mood disorders and cognitive function [4] [5] [9]. This positions mesembrine uniquely among natural neuroactive compounds and bridges indigenous knowledge with contemporary neuropharmacology.

   Properties

   CAS Number

   468-53-1

   Product Name

   Mesembrine

   IUPAC Name

   (3aR,7aR)-3a-(3,4-dimethoxyphenyl)-1-methyl-2,3,4,5,7,7a-hexahydroindol-6-one

   Molecular Formula

   C17H23NO3

   Molecular Weight

   289.4 g/mol

   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

   InChI Key

   DAHIQPJTGIHDGO-IAGOWNOFSA-N

   SMILES

   CN1CCC2(C1CC(=O)CC2)C3=CC(=C(C=C3)OC)OC

   Synonyms

   Mesembrine;(3aR,7aR)-3a-(3,4-dimethoxyphenyl)-1-methyl-2,3,4,5,7,7a-hexahydroindol-6-one

   Canonical SMILES

   CN1CCC2(C1CC(=O)CC2)C3=CC(=C(C=C3)OC)OC

   Isomeric SMILES

   CN1CC[C@@]2([C@H]1CC(=O)CC2)C3=CC(=C(C=C3)OC)OC

2. Mesembrine CAS 468-53-1

   CAS: 468-53-1
   Molecular formula: C17H23NO3
   Molecular weight: 289.37
   EINECS: /

   Synonyms: Mesembrine; (3aR,7aR)-3a-(3,4-dimethoxyphenyl)-1-methyl-2,3,4,5,7,7a-hexahydroindol-6-one; 3a-(3,4-dimethoxyphenyl)-1-methyl-octahydro-1H-indol-6(2H)-one; 6H-Indol-6-one,3a-(3,4-dimethoxyphenyl)octahydro-1-methyl-,(3aR,7aR)-; (+)-Mesembrine; 6H-Indol-6-one,3a-(3,4-dimethoxyphenyl)octahydro-1-methyl-,(3aR-cis)-; (3aR,7aR)-3a-(3,4-dimethoxyphenyl)-1-methyloctahydro-6H-indol-6-one

   What is Mesembrine CAS 468-53-1?

   Mesembrine CAS 468-53-1 is a naturally occurring alkaloid primarily isolated from plants of the Sceletium genus (commonly known as Kanna), which are native to South Africa. Mesembrine is classified as an indole alkaloid and is known for its activity on the central nervous system. Chemically, it functions mainly as a serotonin reuptake inhibitor (SRI) and also shows phosphodiesterase-4 (PDE4) inhibitory activity.

   Specification

   Item	Value
   Appearance	Colorless to light yellow liquid
   Boiling point	419.2±45.0 °C(Predicted)
   Density	1.133±0.06 g/cm3(Predicted)
   Storage conditions	-20°C Freezer

   Feature

   • Natural indole alkaloid: isolated from Sceletium (Kanna) species.
   • Serotonin reuptake inhibitor (SRI): with additional PDE4 inhibitory activity.
   • High-purity reference compound: suitable for pharmaceutical and phytochemical research.

   Application

   • Analytical reference standard: in quality control of Sceletium extracts.
   • Neuropharmacological and CNS-related research
   • Academic and industrial research: on alkaloids and natural bioactive compounds.

   Packaging

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   Mesembrine | 468-53-1 – ChemicalBook

   Apr 24, 2026 · Mesembrine (CAS 468-53-1) information, including chemical properties, structure, melting point, boiling point, density, …

   • Boiling point: 419.2±45.0 °C (Predicted)
   • solubility: Chloroform (Slightly), Methanol (Slightly)

   • Density: 1.133±0.06 g/cm3 (Predicted)
   • storage temp.: 20°C Freezer
3. CAS 468-53-1 ( (+)-Mesembrine) – BOC Sciences

   This study sought to more broadly characterize activity of Sceletium tortuosum and mesembrine in a number of common, rodent …

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