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Speciogynine

(Synonyms: (+)-Speciogynine) 目录号 : GC44923

An Analytical Reference Standard

Speciogynine Chemical Structure

Cas No.:4697-67-0

规格 价格 库存 购买数量
500μg
¥1,696.00
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1mg
¥3,221.00
现货
5mg
¥13,568.00
现货

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Sample solution is provided at 25 µL, 10mM.

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产品描述

Speciogynine is an analytical reference standard that is structurally similar to known opioids. Speciogynine is an alkaloid found in M. speciosa (Kratom in Thai). This product is intended for research and forensic applications.

Chemical Properties

Cas No. 4697-67-0 SDF
别名 (+)-Speciogynine
Canonical SMILES CC[C@@H](C1)[C@@H](/C(C(OC)=O)=C\OC)C[C@@](N1CC2)([H])C3=C2C4=C(OC)C=CC=C4N3
分子式 C23H30N2O4 分子量 398.5
溶解度 DMF: 20mg/mL,DMSO: 10mg/mL,Ethanol: 2mg/mL,Ethanol:PBS(pH 7.2) (1:1): .5mg/mL 储存条件 Store at -20°C
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溶解性数据

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1 mg 5 mg 10 mg
1 mM 2.5094 mL 12.5471 mL 25.0941 mL
5 mM 0.5019 mL 2.5094 mL 5.0188 mL
10 mM 0.2509 mL 1.2547 mL 2.5094 mL
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Research Update

Asymmetric Total Syntheses of Mitragynine, Speciogynine, and 7-Hydroxymitragynine

Chem Pharm Bull (Tokyo) 2022;70(9):662-668.PMID:36047237DOI:10.1248/cpb.c22-00441.

A number of alkaloids found in Mitragyna species belonging to the Rubiaceae family have been shown to have potent biological activity such as analgesic properties. Here, we report the asymmetric total syntheses of mitragynine, Speciogynine, and 7-hydroxymitragynine, which are classified as corynantheine-type monoterpenoid indole alkaloids, isolated from Mitragyna speciosa. These syntheses were accomplished within 12 steps and in >11% total yield from commercial 3-(trimethylsilyl)propanal using an organocatalytic anti-selective Michael reaction and bioinspired transformations.

Total syntheses of mitragynine, paynantheine and Speciogynine via an enantioselective thiourea-catalysed Pictet-Spengler reaction

Chem Commun (Camb) 2012 Dec 28;48(100):12243-5.PMID:23150886DOI:10.1039/c2cc37023a.

The pharmacologically interesting indole alkaloids (-)-mitragynine, (+)-paynantheine and (+)-speciogynine were synthesised in nine steps from 4-methoxytryptamine by a route featuring (i) an enantioselective thiourea-catalysed Pictet-Spengler reaction, providing the tetrahydro-β-carboline ring and (ii) a Pd-catalysed Tsuji-Trost allylic alkylation, closing the D-ring.

Phase I and II metabolites of Speciogynine, a diastereomer of the main Kratom alkaloid mitragynine, identified in rat and human urine by liquid chromatography coupled to low- and high-resolution linear ion trap mass spectrometry

J Mass Spectrom 2010 Nov;45(11):1344-57.PMID:20967737DOI:10.1002/jms.1848.

Mitragyna speciosa (Kratom in Thai), a Thai medical plant, is misused as herbal drug of abuse. Besides the most abundant alkaloids mitragynine (MG) and paynantheine (PAY), several other alkaloids were isolated from Kratom leaves, among them the third abundant alkaloid is Speciogynine (SG), a diastereomer of MG. The aim of this present study was to identify the phase I and II metabolites of SG in rat urine after the administration of a rather high dose of the pure alkaloid and then to confirm these findings using human urine samples after Kratom use. The applied liquid chromatography coupled to low- and high-resolution mass spectrometry (LC-HRMS-MS) provided detailed information on the structure in the MS(n) mode particularly with high resolution. For the analysis of the human samples, the LC separation had to be improved markedly allowing the separation of SG and its metabolites from its diastereomer MG and its metabolites. In analogy to MG, besides SG, nine phase I and eight phase II metabolites could be identified in rat urine, but only three phase I and five phase II metabolites in human urine. These differences may be caused by the lower SG dose applied by the user of Kratom preparations. SG and its metabolites could be differentiated in the human samples from the diastereomeric MG and its metabolites comparing the different retention times determined after application of the single alkaloids to rats. In addition, some differences in MS(2) and/or MS(3) spectra of the corresponding diastereomers were observed.

Activity of Mitragyna speciosa ("Kratom") Alkaloids at Serotonin Receptors

J Med Chem 2021 Sep 23;64(18):13510-13523.PMID:34467758DOI:10.1021/acs.jmedchem.1c00726.

Kratom alkaloids have mostly been evaluated for their opioid activity but less at other targets that could contribute to their physiological effects. Here, we investigated the in vitro and in vivo activity of kratom alkaloids at serotonin receptors (5-HTRs). Paynantheine and Speciogynine exhibited high affinity for 5-HT1ARs and 5-HT2BRs, unlike the principal kratom alkaloid mitragynine. Both alkaloids produced antinociceptive properties in rats via an opioid receptor-independent mechanism, and neither activated 5-HT2BRs in vitro. Paynantheine, Speciogynine, and mitragynine induced lower lip retraction and antinociception in rats, effects blocked by a selective 5-HT1AR antagonist. In vitro functional assays revealed that the in vivo 5-HT1AR agonistic effects may be due to the metabolites 9-O-desmethylspeciogynine and 9-O-desmethylpaynantheine and not the parent compounds. Both metabolites did not activate 5-HT2BR, suggesting low inherent risk of causing valvulopathy. The 5-HT1AR agonism by kratom alkaloids may contribute to the mood-enhancing effects associated with kratom use.

The Chemical and Pharmacological Properties of Mitragynine and Its Diastereomers: An Insight Review

Front Pharmacol 2022 Feb 24;13:805986.PMID:35281925DOI:10.3389/fphar.2022.805986.

Mitragynine, is a naturally occurring indole alkaloid that can be isolated from the leaves of a psychoactive medicinal plant. Mitragyna speciosa, also known as kratom, is found to possess promising analgesic effects on mediating the opioid receptors such as µ (MOR), δ (DOR), and κ (KOR). This alkaloid has therapeutic potential for pain management as it has limited adverse effect compared to a classical opioid, morphine. Mitragynine is frequently regarded to behave like an opioid but possesses milder withdrawal symptoms. The use of this alkaloid as the source of an analgesic candidate has been proven through comprehensive preclinical and clinical studies. The present data have shown that mitragynine is able to bind to opioid receptors, particularly MOR, to exhibit the analgesic effect. Moreover, the chemical and pharmacological aspects of mitragynine and its diastereomers, Speciogynine, speciociliatine, and mitraciliatine, are discussed. It is interesting to know how the difference in stereochemical configuration could lead to the difference in the bioactivity of the respective compounds. Hence, in this review, the updated pharmacological and toxicological properties of mitragynine and its diastereomers are discussed to render a comprehensive understanding of the pharmacological properties of mitragynine and its diastereomers based on their structure-activity relationship study.