Antispasmodics. VIII. Scopolamine Derivatives

Moffett, Robert Bruce; Aspergren, Brooke D.

doi:10.1021/ja01595a051

Cited by 15 publications

(4 citation statements)

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“…Scopolamine (2.0 mmol) was taken in a round bottom flask (50 mL) and 4.0 mL of acetyl chloride was added to it. The reaction mixture was heated on a steam bath for 1.5 h, 8 then cooled to room temperature, neutralized with Na 2 CO 3 (10%) solution, fractionated with ethyl acetate, and concentrated using a rotary evaporator.…”

Section: O-acetylscopolamine (2)mentioning

confidence: 99%

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The diagnostic value of ischemia-modified albumin in the diagnosis of aortic pathology

Eroğlu¹,

Turkmen²,

Menteşe³

et al. 2014

Turk J Med Sci

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This study was designed to synthesize and evaluate derivatives of scopolamine (1) as acetylcholine esterase and protease inhibitors. Scopolamine (1) was extracted from the aerial parts of Datura innoxia through bioassay guided fractionation. Five different derivatives of scopolamine (1) were synthesized, and identified through spectroscopic studies. Their acetylcholine esterase (AChE) and trypsin inhibitory potentials were determined through standard protocols and evaluated from the perspective of structure-activity relationship.The synthesized scopolamine derivatives (2-6) showed remarkable AChE inhibitory activity, except for scopoline (6). The results showed higher enzyme inhibition potential of the synthesized compounds (2-5) as compared to scopolamine (1). Maximum inhibition was exhibited by scopolamine N -oxide (89.9 ± 1.2%, IC 50 = 37.4 ± 1.1 μ M)), followed by scopolamine sulfonic acid (70.3 ± 0.8%, IC 50 = 46.9 ± 1.0 μ M) and O -methyl scopolamine (66.1 ± 1.2%, IC 50 = 94.7 ± 0.8 μ M). All derivatives showed moderate activity against trypsin; maximum activity was exhibited by 6 (54.0 ± 1.4%) with IC 50 = 621.2 ± 3.7 μ M.

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Section: O-acetylscopolamine (2)mentioning

confidence: 99%

“…Compound 1 (0.1 mol) was dissolved in 5 mL of ethanol (95%) and 20 mL of hydrogen peroxide (30%) added. 8 The reaction mixture was stirred for 4 days at room temperature and excess H 2 O 2 was evaporated under vacuum, which resulted in scopolamine-N -oxide (5) as a white amorphous powder (m.p. = 134 • C, 37% yield).…”

Section: Scopolamine-n -Oxide (5)mentioning

confidence: 99%

The diagnostic value of ischemia-modified albumin in the diagnosis of aortic pathology

Eroğlu¹,

Turkmen²,

Menteşe³

et al. 2014

Turk J Med Sci

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“…In the course of developing it for utilization as a pharmaceutically active ingredient in the treatment of asthma and other bronchial disorders, − oxitropium bromide, first synthesized in the 1950s, was found to undergo a dimorphic single-crystal-to-single-crystal phase transition . Initial hot-stage microscopic experiments to investigate the nature of this phase transition immediately indicated that the transition is an example of the thermosalient phenomenon , occasionally colloquially referred to as “jumping crystals”. − …”

Section: Introductionmentioning

confidence: 99%

The Thermosalient Phenomenon. “Jumping Crystals” and Crystal Chemistry of the Anticholinergic Agent Oxitropium Bromide

et al. 2010

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The anticholinergic agent oxitropium bromide possesses rich crystal chemistry, most remarkably exhibiting a strong thermosalient effect ("jumping crystal" effect), a mechanical property with potential applications in organic-based actuators. The thermosalient effect, manifested in forceful jumps of up to several centimeters, was investigated by a combination of structural, microscopic, spectroscopic, and thermoanalytical techniques, providing data on which to base a proposed mechanism for the phenomenon. Direct observation of the effect in a single crystal and structure determination of both phases revealed that the jumping of the crystals is a macroscopic manifestation of a highly anisotropic change in the cell volume. The cell distortion is accompanied by a conformational change of the oxitropium cation, which triggers increased separation between the ion pairs in the lattice at nearly identical separation between the cation and the anion within each ion pair. At the molecular level, the cation acts as a molecular shuttle composed of two rigid parts (epoxy-aza-tricyclic-nonyl portion and phenyl ring) that are bridged by a flexible ester linkage. The structure of the rigid, inert aza-tricyclic portion remains practically unaffected by the temperature, suggesting a mechanism in which the large, thermally accumulated strain is transferred over the ester bridge to the phenyl ring, which rotates to trigger the phase transition. Mechanistic details of the higher temperature solid-state phenomena are also presented. The high-temperature phase can also be obtained by grinding or UV irradiation of the room-temperature phase. In addition, if it is irradiated with UV light in the presence of KBr, the high-temperature phase undergoes intramolecular photochemical rearrangement. Heating the high-temperature phase to slightly below the melting temperature results in an additional solid-state reaction that results in the conversion of the salt to a mixture of neutral compounds.

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“…N-Ethylnorhyoscine and N-propylnorhyoscine were prepared by treating norhyoscine with the appropriate iodoalkane. Apohyoscine was synthesized as described by Moffett and Aspergren (1956) and scopoline prepared by hydrolysis of the parent compound (Willstatter and Berner, 1923).…”

Section: Introductionmentioning

confidence: 99%

Liquid chromatographic determination of hyoscine (scopolamine) in urine using solid phase extraction

Whelpton

Hurst

Metcalfe

et al. 1992

Biomedical Chromatography

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A sensitive method for the determination of hyoscine (scopolamine) in urine is described. After concentration and "clean-up" on C18 and CN solid phase extraction columns, hyoscine was quantified by high performance liquid chromatography with coulometric detection (oxidation at +0.9 V). The limit of detection was 5 ng per sample and the precision for 5 mL samples containing 2 ng/mL was 12.3%. The method was applied to urine samples collected from 12 volunteers wearing Scopoderm TTS patches. The mean excretion rate of unmetabolized hyoscine was 0.45 micrograms/h and 87% of the total hyoscine was present as conjugates. Apohyoscine (aposcopolamine) was identified as a urinary metabolite. The significance of this with regard to hyoscine assays is discussed.

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Antispasmodics. VIII. Scopolamine Derivatives

Cited by 15 publications

References 0 publications

The diagnostic value of ischemia-modified albumin in the diagnosis of aortic pathology

The diagnostic value of ischemia-modified albumin in the diagnosis of aortic pathology

The Thermosalient Phenomenon. “Jumping Crystals” and Crystal Chemistry of the Anticholinergic Agent Oxitropium Bromide

Liquid chromatographic determination of hyoscine (scopolamine) in urine using solid phase extraction

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