AUTHENTICITY CASE STUDY
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1 AUTHENTICITY CASE STUDY HiLIQ NTN Non Tobacco Nicotine HiLIQ, the manufacturer of a product named NTN claims to be synthetic nicotine as a 10% solution in propylene glycol (PG), and to be USP grade purity. This study proves this claim is false.
2 HiLIQ NTN SAMPLE To conduct the authenticity test, Next Generation Labs secured a sample of HiLIQ s NTN. Photographs of the sample can be seen in Figure 1, below: Figure 1: HiLIQ NTN sample STEP ONE: H 1 NMR An H 1 NMR (DCl 3 ) of the solution directly out of the bottle was performed, and the results are shown in Figure 2, below: Figure 2: H 1 NMR of HiLIQ NTN solution The H1NMR spectra is consistent with about a 10% solution of nicotine in propylene glycol.
3 Next, the nicotine was isolated in good yield by first pouring the NTN solution into water, extracting the water layer with dichloromethane, and then the dichloromethane extract was washed repeatedly with copious amounts of water. This dichloromethane layer was extracted with 1% HCl, and then this acidic aqueous extract was washed twice with dichloromethane, and then basified with 10% sodium hydroxide, and the resulting aqueous solution (blue litmus) was extracted with dichloromethane. The dichloromethane was removed by rotary evaporation at about 30mmHg vacuum, and then the residue was subjected to high vacuum to rid of the remaining solvent. A H 1 NMR of the resulting non-viscous, slightly colored oil was carried out, and the results are displayed in Figure 3. Figure 3: H1NMR spectra of isolated nicotine from HiLIQ (NTN) product Figure 3 H1NMR spectra is identical to nicotine.
4 STEP TWO: CHIRAL HPLC ANALYSIS Next, the extracted nicotine was subjected to HPLC utilizing a chiral column. Direct comparison to the tobacco-derived nicotine standard shows NTN nicotine to have very similar, if not the same, stereo-isomeric ratio. This shows conclusively that the nicotine in HiLIQ, NTN is the S isomer in the same as observed for the tobacco-nicotine standard ( natural nicotine). The results are shown in Figure 4. Figure 4: Chiral HPLC Analysis of HiLIQ (NTN) Nicotine and Tobacco-derived Nicotine Standard ( S Nicotine) Figure 4: Blue: tobacco-derived nicotine standard; Red: HiLIQ (NTN) nicotine sample isolated by acid/base extraction to give a non-viscous clear colorless oil (represented by H1NMR displayed in Fig. 3) STEP THREE: RADIO-ISOTOPE ANALYSIS Radio-isotope analysis of the extracted nicotine material was undertaken, where the amounts of 14 C and 13 C and D were measured. If the nicotine was from biological sources, this data would be similar in value to those observed for tobacco nicotine, and not for synthetic nicotine. The results are displayed below in Figure 5; standard tobacco-derived nicotine, and TFN brand synthetic nicotine, are also displayed.
5 Figure 5: Results for the Radiocarbon ( 14 C) and Stable Isotope Ratio (δ 13 C and δd) Analysis Note the values for 14 C levels for the tobacco-derived nicotine standard are different than the 14 C levels for the synthetic nicotine TFN brand. The HiLIQ brand nicotine is essentially the same as 14 C levels of the tobacco-derived nicotine, and different than the TFN brand synthetic nicotine. Also, comparison of the non-radioactive isotopes, the 13 C levels and the Deuterium levels, provide further evidence of the tobacco-derived nature of the nicotine from HiLIQ. These values are essentially the same for HiLIQ (NTN) nicotine and tobacco-derived nicotine standard, and different for the synthetic nicotine (TFN). If HiLIQ (NTN) was synthetic nicotine, but where the chemical ingredients used to make this nicotine were from biological sources, then the values for 13 C and D would be expected to be different. As evidenced by the values presented in Table 1 (below) the 13 C and D levels are essentially the same as the tobacco-derived nicotine, and much different than the TFN brand synthetic nicotine. Table 1: Comparison of 14 C, 13 C, and D Isotope Levels for Tobacco-derived Nicotine and Synthetic Nicotine Sample 14 C 13 C D Tobacco-derived nicotine standard Commercial S-nicotine (tobacco-derived [Alchem]) HiLIQ (NTN) Synthetic Nicotine (TFN)
6 STEP FOUR: LIQUID CHROMATOGRAPHY PROCEDURE In order to evaluate the HiLIQ (NTN) brand of nicotine for the contaminants common to tobacco-derived nicotine, high performance liquid chromatography procedure was carried out according to the USP (USP Pharmacopeia, December 2015). This procedure is designed to qualify and quantify impurities in nicotine samples, and it utilizes 5 impurities common to tobacco nicotine. It is important to note that most of these impurities would not be present in synthetic nicotine. Specifically, the impurities anatabine, anabasine and cotinine would certainly not be found in any reasonable synthetic methodology for producing commercial nicotine. Comparative results for the detection of anatabine are Table 2. Note the high levels of anatabine in both commercial nicotine (Alchem International), are similar to the HiLIQ (NTN) brand, and completely absent in the synthetic nicotine sample (TFN brand). Table 2: Results from HPLC analysis of crude HiLIQ liquid, (NTN) and extracted HiLIQ nicotine (NTN-P) Sample Anatabine Commercial S-nicotine (tobacco-derived [Alchem]) 0.89% HiLIQ (NTN) 0.71% Synthetic Nicotine (TFN) 0% (None detected) CONCLUSION In conclusion, this USP-HPLC data shows that indeed the two main impurities of the HiLIQ (NTN) nicotine are the same impurities found in tobacco-derived nicotine and, do not exist in any synthetic preparation. Based on the radio-isotope data, and the USP-HPLC data, it is concluded that the HiLIQ (NTN) nicotine is not synthetic nicotine, and is tobacco-derived nicotine.
7 Appendix 1 Isotopic Analysis, University of Georgia, Dr. Randy Culp Center for Applied Isotope Studies TEL 120 Riverbend Road Athens, Georgia FAX rculp@uga.edu February 13, 2017 Dr. Michael Arnold Next Generation Labs LLC 8549 Wilshire Blvd. #1421 Beverly Hills, CA Dear Dr. Arnold, Listed below are the results for the Radiocarbon (14C) and Stable Isotope Ratio (δ13c and δd) analysis for the sample received by our laboratory January 31, Sam ple NTN P Lot Received 1/31/ C ± 1 σ 0.09 δ 13 C ± 1 σ 0.08 δd -177 ± 1 σ 5 14C activity is in disintegrations per minute per gram carbon (dpm/g C). (± 1 σ) δ13c (13C/12C) is in parts per mil (o/oo) relative to the international standard PDB. (± 1 σ) δd (D/H) is in parts per mil (o/oo) relative to the international standard V-SMOW. (± 1 σ) Calculation of uncertainty provided upon request. The 14C activity of Nicotine Lot NTN P is equivalent to 102% of the 2016 and present day reference activity 13.8 dpm/gc. This indicates no addition or dilution with fossil fuel derived material to this sample. 14C If we can be of any further assistance, or if you would like to discuss these results please do not hesitate to call. Sincerely, Randy Culp, PhD Associate Director C.A.I.S. Inv. No: The University of Georgia Center for Applied Isotope Studies is accredited to ISO/IEC 17025:2005 standard by PJLA, Inc. The University of Georgia is an Equal Opportunity, Affirmative Action, Veteran, Disability Institution
8 Appendix 2 USP-HPLC Analysis of HiLIQ (NTN) Nicotine ACTA Laboratories, Inc.
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