The structure of mitragynine hydroiodide

Zacharias, David E.; Rosenstein, R. D.

doi:10.1107/s0365110x65002499

Cited by 43 publications

(30 citation statements)

References 2 publications

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“…Table 2 shows the key bond lengths, angles and dihedrals of our calculated lowest energy mitragynine conformer at both MMFF94s and B3LYP/6-31G(d,p) levels, and those obtained from X-ray crystallography [11, 12]. It can be seen that our calculated geometry and all the ring conformation using both MMFF94s and B3LYP methods match very well with experiment, especially with the recent structure of ref 12.…”

Section: Resultssupporting

confidence: 61%

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Computational study on the conformations of mitragynine and mitragynaline

Liu

McCurdy

Doerksen

2010

Journal of Molecular Structure: THEOCHEM

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A conformational search on mitragynine and mitragynaline, natural products isolated from the leaves of Mitragyna speciosa, was performed using the MMFF94s force field and the quantum mechanical B3LYP method. The main difference for the mitragynine conformers is caused by the position of the lone pair of the nitrogen shared by rings 3 and 4. Specifically, the lone pair can be syn or anti to the exocylic ethyl group on ring 4. Syn was found to be lower in energy than anti, because of less steric hindrance between the ethyl and the methylene group adjacent to the N in ring 3. The geometrical parameters for the lowest energy conformer of mitragynine are in excellent agreement with the published X-ray crystal structure's geometry. Because it has one more double bond, mitragynaline has less conformational freedom than mitragynine. The main possible conformational choice in mitragynaline is for orientational flexibility of a C-C single bond in ring 3. The finding of two low energy conformers of mitragynaline differing in ring 3 conformation matches reported X-ray crystal structural data.

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Section: Resultssupporting

confidence: 61%

“…The first X-ray crystal structure of mitragynine hydroiodide salt, including absolute configuration of the hydroiodide and hydrobromide, was reported in 1965 [11]. Recently, the crystal structure of mitragynine obtained from ethanol solvent [12] as well as of mitragynaline and corynatheidaline [1, 13] were also published.…”

Section: Introductionmentioning

confidence: 99%

Computational study on the conformations of mitragynine and mitragynaline

Liu

McCurdy

Doerksen

2010

Journal of Molecular Structure: THEOCHEM

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“…Kratom has been also used as a substitute for opium and for withdrawal treatment of morphine addicts [4]. The chemical structures and pharmacological properties of mitragynine and its analogues have been much studied [2,[4][5][6]. As well as narcotic, analgesic, and stimulant-like effects, due to agonistic action on opioid receptors [2,[7][8][9], mitragynine and its analogues have been shown to have inhibitory effects on neurogenic systems, in animal experiments [10][11][12].…”

Section: Introductionmentioning

confidence: 98%

Quantitative analysis of mitragynine in human urine by high performance liquid chromatography-tandem mass spectrometry

Tran

Nelsen

et al. 2009

Journal of Chromatography B

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“…The alkaloid content of the leaves of Mitragyne speciosa is about 0.5%, about half of which is comprised of mitragynine ( 1 ). Although the structure determination of 1 has a rich history,1-4 the actual structure of 1 was unambiguously confirmed in 1964 when the X-ray crystal structure of mitragynine hydroiodide salt was completed by Zacharias 5. The first formal study of the pharmacology of mitragynine ( 1 ) indicated that it was a central nervous system (CNS) stimulant 6,7.…”

Section: Introductionmentioning

confidence: 99%

General Approach to the Total Synthesis of 9-Methoxy-Substituted Indole Alkaloids: Synthesis of Mitragynine, as well as 9-Methoxygeissoschizol and 9-Methoxy-N_b-methylgeissoschizol

Yin

Zhou

et al. 2008

J. Org. Chem.

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Herein the full details of the synthesis of the 9-methoxy-substituted Corynanthe indole alkaloids mitragynine (1), 9-methoxygeissoschizol (3) and 9-methoxy-Nb-methylgeissoschizol (4) are described. Initially an efficient synthetic route to the optically active 4-methoxytryptophan ethyl ester 20 on a multigram scale was developed via a Mori-Ban-Hegedus indole synthesis. The ethyl ester of (D)-4-methoxytryptophan 20 was obtained with a radical-mediated regioselective bromination of indoline 12 serving as a key step. Alternatively, the key 4-methoxytryptophan intermediate 22 could be synthesized by the Larock heteroannulation of aryl iodide 10b with the internal alkyne 21a. The use of the Boc protected aniline 10b was crucial to the success of this heteroannulation. The α,β-unsaturated ester 6 was synthesized via the Pictet-Spengler reaction as the pivotal step. This was followed by a Ni(COD)2 mediated cyclization to set up the stereocenter at C-15. The benzyloxy group in 31 was removed to provide the intermediate ester 5. This chiral tetracyclic ester 5 was employed to accomplish the first total synthesis of 9-methoxygeissoschizol (3) and 9-methoxy-Nb-methylgeisso-schizol (4) as well as the opioid agonistic indole alkaloid mitragynine (1).

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The structure of mitragynine hydroiodide

Cited by 43 publications

References 2 publications

Computational study on the conformations of mitragynine and mitragynaline

Computational study on the conformations of mitragynine and mitragynaline

Quantitative analysis of mitragynine in human urine by high performance liquid chromatography-tandem mass spectrometry

General Approach to the Total Synthesis of 9-Methoxy-Substituted Indole Alkaloids: Synthesis of Mitragynine, as well as 9-Methoxygeissoschizol and 9-Methoxy-N_b-methylgeissoschizol

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The structure of mitragynine hydroiodide

Cited by 43 publications

References 2 publications

Computational study on the conformations of mitragynine and mitragynaline

Computational study on the conformations of mitragynine and mitragynaline

Quantitative analysis of mitragynine in human urine by high performance liquid chromatography-tandem mass spectrometry

General Approach to the Total Synthesis of 9-Methoxy-Substituted Indole Alkaloids: Synthesis of Mitragynine, as well as 9-Methoxygeissoschizol and 9-Methoxy-Nb-methylgeissoschizol

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General Approach to the Total Synthesis of 9-Methoxy-Substituted Indole Alkaloids: Synthesis of Mitragynine, as well as 9-Methoxygeissoschizol and 9-Methoxy-N_b-methylgeissoschizol