D-1012

Determination of Huperzine A, Theacrinem Caffeine, and Methylliberine by HPLC-UV

Section D — Laboratory Operations and Specifications 10 pages

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1.0 Purpose 
 
 This document describes the analytical procedure for the determination of Huperzine A,
 
 Theacrine, Caffeine & Methylliberine in raw materials and finished products.
 
 2.0 Scope 
 
 This procedure applies to the identification and quantification of Huperzine A, Theacrine,
 
 Caffeine & Methylliberine in raw materials and finished products. This method was validated
 under protocol PRTCL-22-0064. 
 
 3.0 Responsibility 
 
 3.1 It is the responsibility of QC and Analytical chemists who have verified their ability to
 execute this procedure to follow this procedure. 
 
 3.2 It is the responsibility of QC Laboratory Management to implement this procedure and
 to ensure that the procedure is being followed. 
 
 3.3 It is the responsibility of QC Laboratory Management and/or Analytical Development
 Personnel to keep this procedure current with the associated monographs and laboratory
 
 practices. 
 
 4.0 Definitions 
 
 4.1 QC — Quality Control 
 
 4.2 AcOH — Acetic Acid 
 
 4.3 MeOH — Methanol 
 
 
 

[SOP D-101 | Page 2 of 10]

 Standard Operating Procedure SOP No Rev 
 Determination of Huperzine A, Theacrine, Caffeine & D-1012 Page 2 of 
 10 
 Methylliberine by HPLC-UV 
 
 4.4 | ACS-— American Chemical Society 
 
 4.5 HPLC — High Performance Liquid Chromatography 
 
 4.6 UV-Vis — Ultraviolet-Visible (Detection) 
 
 5.0 References 
 
 5.1 PRTCL-22-0064, Protocol, Validation of an Analytical Method for the Determination
 
 of Huperzine A, Theacrine, Caffeine & Methylliberine by HPLC-UV 
 
 5.2. Development of a Sensitive High Performance Liquid Chromatographic Method with
 
 Simple Extraction for Simultaneous Determination of Huperzine A and Huperzine B in
 the Species Containing Lycopodium Alkaloids. Zhang et al., Journal of AOAC
 
 International Vol. 92, No. 4, 2009, pp. 1060-63. 
 
 6.0 Supplies 
 
 6.1 Chemicals — All reagents are ACS grade or better 
 
 6.1.1 Milli-Q Water 
 
 6.1.2 MeOH 
 
 6.1.3 AcOH 
 
 6.1.4 Huperzine A Reference Standard 
 
 6.1.5 Caffeine Reference Standard 
 
 6.2 Supplies and Glassware 
 
 6.2.1 HPLC vials, 12mm X 32mm with screw cap enclosures w/ septa 
 
 6.2.2. Volumetric glassware 
 
 6.2.3 Weigh paper 
 
 

[SOP D-101 | Page 3 of 10]

 Standard Operating Procedure SOP No Rev 
 Determination of Huperzine A, Theacrine, Caffeine & | D-1012 Page 3 of 
 10 
 Methylliberine by HPLC-UV 
 
 6.2.4 Syringes with 0.45 nylon filters 
 
 6.3. Equipment 
 
 6.3.1 Suitable gradient HPLC system consisting of a pump, autosampler, column oven
 and UV-Vis detector with a chromatographic data handling system
 
 6.3.2 Analytical Balance 
 
 6.3.3. Micro Analytical Balance 
 
 6.3.4 Wrist Action Shaker 
 
 6.3.5 Sonicator Bath 
 
 7.0 Procedure 
 
 7.1 Mobile Phase & Diluent Preparation 
 
 7.1.1. Mobile Phase 
 
 7.1.1.1. Mobile Phase A - Add 2ml AcOH to 1000m1 water and mix well.
 
 7.1.1.2 Mobile Phase B —-MeQOH. 
 
 7.1.2 Extraction Solvent / Diluent 
 
 7.1.2.1 20% MeOH (20:80 MeOH/H20) 
 
 7.1.2.2 Use MeOH to extract Huperzine A from raw material and finished
 product matrices. Prepare the final, working solution such that the
 
 composition is 20% MeOH. 
 
 7.1.2.3 Use 20% MeOH to extract Theacrine, Caffeine & Methylliberine raw
 
 materials. Use MeOH to extract Theacrine, Caffeine & Methylliberine
 from finished product matrices. Prepare the final, working solution
 
 such that the composition is 20% MeOH. 
 
 

[SOP D-101 | Page 4 of 10]

 Standard Operating Procedure SOP No Rev 
 Page 4 of 
 Determination of Huperzine A, Theacrine, Caffeine & | D-1012 0 
 10 
 Methylliberine by HPLC-UV 
 7.2 Standard Prep 
 
 (ee Prepare Huperzine A stock at 0.05 mg/ml in MeOH. Sonicate briefly to
 
 dissolve, then dilute 1:5 with MeOH. Dilute a further 1:5 with water. (Note:
 Allow the heat of mixing generated when combining MeOH with water to
 
 dissipate and equilibrate to room temperature prior to volumetric glassware QS.)
 
 Tadd Apply Relative Response Factors (RRFs) in Section 7.7.1 for quantitation of
 Theacrine and Methylliberine. 
 
 7.2.3 Alternatively, Theacrine and Methylliberine reference standard materials may
 be used. 
 
 7.2.4 Prepare Caffeine working standard at ~ 0.075 mg/ml in 20% MeOH.
 
 7.2.5 Alternative standard preparations are acceptable as long as the preparations are
 
 within the linear range of this method. 
 
 7.3 Sample Preparation 
 
 7.3.1 Specific sample testing details are provided in each products profile. If a
 specific testing details section is not available, follow preparation procedure as
 
 described below, maintaining concentration within the linear range of this
 
 method. 
 
 7.3.2 The validated linear ranges for the analytical method are 0.47 — 3.15 pg/mL
 
 Huperzine A, 44.3 — 103.4 ug/mL Theacrine, 44.2 — 103.2 ug/mL Caffeine and
 15.3 — 35.7 ug/mL Methylliberine. 
 
 7.3.3 Extract sufficient sample (based on the raw material manufacturer assay value /
 finished product profile) with Extraction Solvent in order to generate a
 
 concentration that is within the validated linear range. Shake mechanically at
 ~60% volume for 10 minutes. QS to volume and sonicate for 10 minutes. Make
 
 any final dilutions, then filter a 5ml aliquot for analysis, discarding the first 3-
 
 4m of filtrate. 
 
 

[SOP D-101 | Page 5 of 10]

 Standard Operating Procedure SOP No Rev 
 Determination of Huperzine A, Theacrine, Caffeine & | D-1012 0 : a of 
 Methylliberine by HPLC-UV 
 
 7.4 HPLC Parameters 
 
 7.4.1. Column: Phenomenex Luna Ci8(2), 4.6 x 250mm, 100A, 5m (Or Equivalent)
 
 7.4.2 Column Temperature: 30°C 
 
 7.4.3. Flowrate: 1.0 mL/min 
 Time, min %A %B 
 rl . a 0 82 18 
 7.4.4 Mobile Phase — Gradient: 6 89 18 
 15 30 70 
 boul 82 18 
 20 82 18 
 7.4.5 Wavelength: 
 
 7.4.5.1. Huperzine A - 310 nm 
 
 7.4.5.2 Theacrine, Caffeine & Methylliberine - 287 nm 
 
 7.4.6 Injection Volume: 
 
 7.4.6.1 Huperzine A - 15 ub 
 
 7.4.6.2 Theacrine, Caffeine & Methylliberine - 5 uL 
 
 7.4.7 Run Time: 20 minutes 
 
 7.4.7.1 If desired, it is permissible to employ a 10 minute isocratic run time at
 
 18% Mobile Phase B for Huperzine A standard injections.
 
 7.4.8 Recommended 3-D Spectral Range (for Identification): 225nm - 350nm
 
 7.5 Recommended Sequence 
 
 7.5.1 Make at least 2 injections of the Diluent. 
 
 7.5.2. Make at least five (5) injections of Working Standard. 
 
 7.5.3. Make a single injection of each Sample Preparation. 
 
 

[SOP D-101 | Page 6 of 10]

 Standard Operating Procedure SOP No Rev 
 Determination of Huperzine A, Theacrine, Caffeine & D-1012 0 Page 6 of 
 10 
 Methylliberine by HPLC-UV 
 
 7.5.4 Make a single injection of the Working Standard after every ten (10) sample
 injections or at the end of the run. 
 
 7.6 System Suitability Requirements 
 
 7.6.1. The %RSD of five (5) consecutive standard injections is NMT 2%.
 
 7.6.2. The %RSD of all standard injections is NMT 3%. 
 
 7.6.3 If present, any interference in the diluent should be subtracted out of the sample
 
 and standard peak areas. 
 
 7.7 Example calculations for determining % Assay / LC: 
 
 1.7.1 % = Be x WisaX? y “spl y 100 x (SS/x( RLRFA)) 
 Re Vstd SA 
 
 R,, Sample peak area 
 
 R, Mean (n=All) standard peak area 
 
 Wt..4 Weight of the reference standard, mg 
 
 V na Volume of the standard preparation accounting for dilutions, ml
 
 P Purity of the reference standard in decimal format 
 
 SA Sample amount, mg 
 
 Vint Volume of the sample preparation accounting for dilutions, ml
 
 RRF Equal to 0.694 for Theacrine when using Caffeine as Reference
 
 Standard. Equal to 0.763 for Methylliberine when using Caffeine as
 
 Reference Standard. 
 SS Use average dosage weight for solids or use serving size specified in
 
 Product Profile for powders and liquids. Use “1” for raw materials.
 
 LA Label Amount specified in Product Profile. Use “1” for raw
 
 materials. 
 
 

[SOP D-101 | Page 7 of 10]

 Standard Operating Procedure SOP No Rev 
 Determination of Huperzine A, Theacrine, Caffeine & D-1012 Page 7 of 
 10 
 Methylliberine by HPLC-UV 
 
 7.8 System Wash, Column Wash and Column Storage 
 
 7.8.1 Wash and store the column in 75:25 ACN / Water 
 
 

[SOP D-101 | Page 8 of 10]

 Standard Operating Procedure SOP No Rev 
 Determination of Huperzine A, Theacrine, Caffeine & | D-1012 0 Page 8 of 
 10 
 Methylliberine by HPLC-UV 
 
 8.0 Chromatograms 
 
 8.1 Typical Diluent Chromatograms 
 
 0.200 5% HupA FP Run 10-21-22 #2 Diluent UV_VIS_1 WL310.am
 4| mAU 
 
 -0.020- 
 -0.040-+ 
 -0.060- 
 -0.080- 
 -0.100- 
 -0.120- 
 
 -0.1404 
 -0.15000 95 | a10 15 a2e 0ae a a ae e2e 5a e3.0 S35 40 ee 45 5E0 S5 5R 60 R65 7. 0 S75S 80 A,85 AS90 95 100
 % Gaming Stimulants Run 10-19-2#22 Diluent UV_VIS_1 WVL:287 nm
 1 mAU 
 
 

[SOP D-101 | Page 9 of 10]

 Standard Operating Procedure SOP No Rev 
 Page 9 of 
 Determination of Huperzine A, Theacrine, Caffeine & | D-1912 
 10 
 Methylliberine by HPLC-UV 
 8.2 Typical Standard Chromatograms 
 
 500 3 HupAFP Run 10-21-2#28 UV MS_1VWL310nm
 mAU 
 ;1-HupA-5.267 
 
 ee A 
 
 3 Gaming Stimulants Run 10-19-2#23 UV_MS_1 VWVL:287 nm
 mAU 
 1 - Theacrine - 12.123 
 
 2 - Caffeine - 13.220 
 
 5 - Methyilliberine - 15.970
 
 TW seam 
 
 SSS ee een a! 
 
 

[SOP D-101 | Page 10 of 10]

 Standard Operating Procedure SOP No Rev 
 D-1012 0 Page 10 of 
 Determination of Huperzine A, Theacrine, Caffeine & 
 10 
 Methylliberine by HPLC-UV 
 8.3 Typical Finished Product Chromatograms 
 
 @ HupA FP Run 10-21-22 #8 EP-4 UV_VIS_1 WVL:310 nm
 ]| mau 
 
 j1 - HupA - 5.253 
 
 = er re ee emer ace en ee ns om Cm ene Cae Se Ca Sa Ce eel BN SL ae Ca ee RO | NL A Sane a CS Oa TO. eens a Aa GA A a es Tae (a RR a
 
 Run 10-19-2#29 FP-1 UV_VIS_1 WVL:287 nm
 
 2 - Caffeine - 13.227 
 
 13 - Methylliberine - 15.977
 
 T oe ee 
 
 9.0 Revision History 

| Rev | Date | Description of Changes | CCR # | By |
|-----|----------|------------------------|-------|----|
| 0 | 11/10/22 | New procedure. N/A C. Perry | - | - |