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Usage

Uses

Used in Pharmaceutical Industry:
R-(+)-Hyoscyamine is used as a pharmaceutical compound for its inhibitory activity against cholinesterases. This property makes it a potential candidate for the development of drugs targeting conditions related to the overactivity of cholinesterases, such as Alzheimer's disease and myasthenia gravis.
Used in Research and Development:
In the field of research and development, R-(+)-Hyoscyamine serves as an important compound for studying the effects of cholinesterase inhibition and its potential applications in various therapeutic areas. Its unique 2R-configuration also provides valuable insights into the structure-activity relationships of cholinesterase inhibitors.
Used in Synthesis of Other Compounds:
R-(+)-Hyoscyamine can be utilized as a starting material or intermediate in the synthesis of other biologically active compounds, such as Atropine, which has various applications in medicine, including the treatment of certain conditions related to the nervous system and as a preoperative medication.

InChI:InChI=1/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13?,14?,15?,16-/m0/s1

Upstream product

• 529-64-6 Tropic acid 
• 17126-67-9 (+)-(R)-tropic acid 
• 131682-38-7 (+)-3-acetoxy-2-phenylpropionic acid 
• 16202-15-6 (S)-tropic acid 
• 37504-67-9 (αS)-α-(acetoxymethyl)benzeneacetic acid 
• 51-55-8 Atropine 
• 5908-99-6 atropine sulfate 
• 120-29-6 3-tropanol 
• 51-55-8 atropine 
• 3144-16-9 (1S)-10-camphorsulfonic acid 

Relevant academic research and scientific papers

Comparison of three S-β-CDs with different degrees of substitution for the chiral separation of 12 drugs in capillary electrophoresis

Three kinds of sulfated β-cyclodextrin (S-β-CD), including a single isomer, heptakis-6-sulfato-β-cyclodextrin (HS-β-CD), degree of substitution (DS) of 7, which was synthesized in our laboratory and another two commercialized randomly substituted mixtures, a sulfated β-cyclodextrin with DS of 7 to 11, as well as a highly sulfated-β-cyclodextrin with DS of 12 to 15, were used for the enantioresolution of 12 drugs (the β-blockers, phenethylamines, and anticholinergic agents) in capillary electrophoresis. The enantioseparation under varying concentrations of S-β-CD and background electrolyte pH were systematically investigated and compared. Based on the experimental results, the effect of the nature of S-β-CD and analyte structure on the enantioseparation is discussed.

Strategy Approach for Direct Enantioseparation of Hyoscyamine Sulfate and Zopiclone on a Chiral αl-Acid Glycoprotein Column and Determination of Their Eutomers: Thermodynamic Study of Complexation

Rapid and simple isocratic high-performance liquid chromatographic methods with UV detection were developed and validated for the direct resolution of racemic mixtures of hyoscyamine sulfate and zopiclone. The method involved the use of αl-acid glycoprotein (AGP) as chiral stationary phase. The stereochemical separation factor (Greek small letter alpha with tonos) and the stereochemical resolution factor (Rs) obtained were 1.29 and 1.60 for hyoscyamine sulfate and 1.47 and 2.45 for zopiclone, respectively. The method was used for determination of chiral switching (eutomer) isomers: S-hyoscyamine sulfate and eszopiclone. Several mobile phase parameters were investigated for controlling enantioselective retention and resolution on the chiral AGP column. The influence of mobile phase, concentration and type of uncharged organic modifier, ionic strength, and column temperature on enantioselectivity were studied. Calibration curves were linear in the ranges of 1-10 μg mL-1 and 0.5-5 μg mL-1 for S-hyoscyamine sulfate and eszopiclone, respectively. The method is specific and sensitive, with lower limits of detection and quantifications of 0.156, 0.515 and 0.106, 0.349 for S-hyoscyamine sulfate and eszopiclone, respectively. The method was used to identify quantitatively the enantiomers profile of the racemic mixtures of the studied drugs in their pharmaceutical preparations. Thermodynamic studies were performed to calculate the enthalpic ΔH and entropic ΔS terms. The results showed that enantiomer separation of the studied drugs were an enthalpic process.

Differential analgesic activity of the enantiomers of atropine derivatives does not correlate with their muscarinic subtype selectivity

The enantiomers of several tropic and p-substituted tropic acid esters related to atropine obtained by esterification under non-racemizing conditions after resolution of the corresponding racemic acids [(+)- and (-)-18, (+)- and (-)-19] are reported. They were tested in vitro on muscarinic subtype receptors and in vivo for their analgesic activity on mice. As in the case of the lead compound, R-(+)-hyoscyamine, these substances show enantioselectivity in analgesic tests, the eutomers being the R-(+) or R-(+)-p-substituted tropic acid derivatives. However, this property, which is a consequence of increased central release of ACh, seems unrelated to muscarinic subtype selectivity insofar as the compounds are unable to discriminate muscarinic subtype receptors. A possible explanation of these results which does not involve subtype selectivity is proposed, based on the recently developed concept of inverse agonism.

RESOLUTION OF ENANTIOMERS BY HPLC ON CELLULOSE TRANS- AND CIS-TRIS(4-PHENYLAZOPHENYLCARBAMATE)

Cellulose tris(4-phenylazophenylcarbamate) ( CPAPC ) having azobenzene pendant groups was adsorbed on silica gel to use as a chiral stationary phase for HPLC.Pure trans-CPAPC resolved many racemic compounds, whereas 70 percent cis-CPAPC showed very poor resolving power.