Phenyl d5 alprazolam

Formononetin, biochanin A, daidzein, genistein, caffeine, [trimethyl-¹³C₃]-caffeine, tolbutamide, dextromethorphan, [methyl-d₃]-dextromethorphan, alprazolam, [phenyl-d₅]-alprazolam, and Helix pomatia β-glucuronidase and arylsulfatase were purchased from Sigma-Aldrich (St. Louis, MO). [butyl-d₉]-4-Hydroxy-tolbutamide was purchased from Toronto Research Chemicals (Toronto, Canada). LC-MS grade acetonitrile and methanol were purchased from VWR (Radnor, PA), and LC-MS grade formic acid was purchased from Thermo Scientific (Rockford, IL). Water was prepared using an Elga Purelab Ultra (Siemens Water Technologies, Woodridge, IL) water purification system. Blank serum obtained from individual donors was purchased from BioIVT (Westbury, NY). The red clover dietary supplement was standardized chemically and biologically^{32 (link)} and had been used in our previous clinical trials.^{33 (link),34 (link)}

Caffeine, [trimethyl-¹³C₃]-Caffeine, tolbutamide, dextromethorphan, [methyl-d₃]-dextromethorphan, alprazolam, and [phenyl-d₅]-alprazolam were purchased from Sigma-Aldrich (St. Louis, MO), and [butyl-d₉]-4-hydroxy-tolbutamide was purchased from Toronto Research Chemicals (Toronto, Canada) (Figure 1). LC-MS grade acetonitrile and methanol were purchased from VWR (Radnor, PA), and LC-MS grade formic acid was purchased from Thermo Scientific (Rockford, IL). Water was prepared using an Elga Purelab Ultra (Siemens Water Technologies, Woodridge, IL) water purification system.
Pooled human serum and serum from individual donors were purchased from Valley Biomedical Products & Services (Winchester, VA), Innovative Research (Novi, MI), Sigma-Aldrich (St. Louis, MO), and BioIVT (Westbury, NY). Serially drawn serum samples from women who had been administered an oral cocktail of 100 mg Caffeine, 250 mg tolbutamide, 30 mg dextromethorphan, and 2 mg alprazolam were obtained from the UIC/NIH Center for Botanical Dietary Supplements Research (registered with ClinicalTrials.gov as , UIC Institutional Review Board #2015-0651). These serum samples contained no patient identifying information. All serum was stored at −80 °C until use.

β-Glucuronidase and arylsulfatase were purchased from Sigma-Aldrich (St. Louis, MO). Formic acid (LC-MS grade) was purchased from Thermo Scientific (Rockford, IL), and methanol and acetonitrile (LC-MS grade) were purchased from VWR (Radnor, PA). Water was prepared using an ElgaPurelab Ultra (Siemens Water Technologies, Woodridge, IL) water purification system. Prenylated hop phenols were prepared from hops at the University of Illinois at Chicago/National Institutes of Health (UIC/NIH) Center for Botanical Dietary Supplements Research (Chicago, IL), structures were confirmed using high resolution mass spectrometry and NMR, and the purities were >95% by HPLC as described previously.^{14 (link)} Caffeine, [trimethyl-¹³C₃]-Caffeine, tolbutamide, dextromethorphan, [methyl-d₃]-dextromethorphan, alprazolam, and [phenyl-d₅]-alprazolam were purchased from Sigma-Aldrich (St. Louis, MO), and [butyl-d₉]-4-hydroxy-tolbutamide was purchased from Toronto Research Chemicals (Toronto, Canada). Serum from individual donors that was free of all probe substrates was purchased from Innovative Research (Novi, MI).