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1 Australian Government National Measurement Institute REFERENCE MATERIAL ANALYSIS REPORT Report ID: D447b Compound Name: (±)-N-Formylamphetamine Description: Clear light yellow liquid Collection Number: D447b ` Batch Number: 09-D-25 Chemical Formula: C 10 H 13 NO Molecular Weight: CAS No: Batch production completed: September 2009 Structure: Synonyms: Me NHCHO N-(α-Methylphenethyl)formamide N-(1-Methyl-2-phenylethyl)formamide 1-Phenyl-2-(N-formylamino)propane Purity (mass fraction): 95 % minimum This reference material has NOT been extensively quantified by the Chemical Reference Materials team, NMI. This material should be considered for use in qualitative analysis only. Purity estimate obtained from a combination of analytical techniques. The purity estimate by traditional analytical techniques was obtained by subtraction from 100% of total impurities by GC-FID, thermogravimetric analysis, Karl Fischer analysis and 1 H NMR. Supporting evidence is provided by QNMR and elemental microanalysis. GC-FID: Instrument: Agilent 6890N Column: HP-1, 29.9 m 0.32 mm I.D µm Program: 80 C (1 min), 10 C/min to 120 C (10 min), 20 C/min to 300 C (3 min) Initial analysis: Mean = 97.6 %, s = 0.02% (10 sub samples in duplicate, October 2009). GC-FID: Instrument: Varian CP-3800 Column: VF-1MS, m 0.32 mm I.D µm Program: 80 C (1 min), 10 C/min to 120 C (10 min), 20 C/min to 300 C (3 min) Initial analysis: Mean = 97.6 %, s = 0.06% (7 sub samples in duplicate, October 2009). GC-FID: Instrument: Agilent 6890N Column: HP-1, m 0.32 mm I.D µm Program: 100 C (0.5 min), 10 C/min to 120 C (10 min), 15 C/min to 260 C (3min), 30 C/min to 300 C (3 min) Initial analysis: Mean = 97.9 %, s = 0.01% (5 sub samples in duplicate, October 2010). Page 1 of 4
2 HPLC: Instrument: Waters Model 600E pump, 717 plus Autosampler Column: Novapak C18, 5µm (3.9 mm I.D x 150 mm) Mobile Phase: Methanol/water/diethylamine (60/40/0.5) ph 8.5 buffered with orthophosphoric acid 85% Flow Rate: 1.0 ml/min Detector: PDA max plot Retention time: 9.1 min Initial analysis: Mean = 98.88%, s = 0.20 (1 sub sample run triplicate, December 2009) QNMR: Instrument: Bruker Avance III-400 Field strength: 400 MHz Solvent: CDCl 3 Internal standard: Trioxane Purity estimate: Mean = 98.2%, s = 0.20 (1 sub sample run triplicate, November 2009) Thermogravimetric analysis: Volatile content not determined due to volatility of the material. Karl Fischer analysis: Moisture content 1.9 % mass fraction (November 2009) Moisture content 2.4 % mass fraction (November 2010) Page 2 of 4
3 Spectroscopic characterisation data GC-MS: Instrument: Agilent 6890/5973 Column: VF-1ms, 14.9 m 0.25 mm I.D µm Program: 60 C (1min), 10 C/min to 200 C, 30 C/min to 300 C (3 min) Injector: 250 C Transfer line temp: 300 C Carrier: Helium, 1.0 ml/min Split ratio: 20/1 The retention time of the parent compound is reported along with the major peaks in the mass spectrum. The latter are reported as mass/charge ratios and (in brackets) as a percentage relative to the base peak. 8.6 min: 163 (M +, 1), 118 (100), 117 (21), 91 (39), 72 (77), 65 (15), 44 (54) m/z TLC: Kieselgel 60F 254. Toluene/acetone/95%ethanol/conc.ammonia (45/45/7/3). Single spot observed, R f = Developed with acidified iodoplatinate. IR: Instrument: Biorad FTS300MX FT-IR Range: cm -1, neat oil. Peaks: 1659, 1532, 1496, 1450, 1380, 1243, 769, 733 cm -1 1 H NMR: Instrument: Bruker Avance III-400 Field strength: 400 MHz Solvent: CDCl 3 (7.26 ppm) Spectral data: δ 1.11 (2.3 H, d, J = 6.6 Hz), 1.23 (0.7 H, d, J = 6.6 Hz), (2H, m), 3.69 (0.2 H, sep), 4.31 (0.8 H, sep), 5.58 (0.8 H, bs), 5.78 (0.2 H, bs), (5H, m), 7.76 (0.2 H, d, J = 12 Hz), 8.03 (0.8 H, s) ppm Doubling of the signals is due to restricted rotation about the amide bond. 13 C NMR: Instrument: Bruker Avance III-400 Field strength: 100 MHz Solvent: CDCl 3 (77.16 ppm) Spectral data: δ 20.1, 22.0, 42.4, 44.6, 45.1, 50.0, 126.7, 127.0, 128.5, 128.8, 129.5, 137.3, 137.7, 160.6, ppm Doubling of the signals is due to restricted rotation about the amide bond. Microanalysis: Found: C = 72.7%; H = 8.1%; N = 8.7% (October 2009) Calc: C = 72.7%; H = 8.1%; N = 8.5% (Calc. for C 10 H 13 NO. 0.11H 2 O) Calc: C = 73.6%; H = 8.0%; N = 8.6% (Calc. for C 10 H 13 NO) Page 3 of 4
4 Expiration of certification The property values are valid till 19 th October 2013, i.e. three years from the date of re-certification provided the unopened material is handled and stored in accordance with the recommendations below. The material as issued in the unopened container and stored as recommended below should be suitable for use beyond this date, subject to confirmation of batch stability from the issuing body. The expiry date/shelf life does not apply to sample bottles that have been opened. In such cases it is recommended that the end-user conduct their own in-house stability trials. The long-term stability of the compound in solution has not been examined. This material has been given a shelf life of 3 years from the date of re-certification. The material will be re-tested on an annual basis to ensure that the property values are still valid. In the event a product fails the stability trial, notification will be sent to all impacted customers. In the absence of stability data the measurement uncertainty at the 95% coverage interval has been expanded to accommodate any potential change in the property value. The stability component has been estimated from stability trials conducted on similar materials by NMI Australia over the last 10 years. Homogeneity assessment The homogeneity of the material was assessed using purity assay by GC-FID on five randomly selected 1-2 mg samples of the material. The material was judged to be homogeneous at this level of sampling as the variation in analysis results between samples was not significantly different at a 95% confidence level from that observed on repeat analysis of the same sample. Recommended storage When not in use this material should be stored at or below 4 ºC in a closed container in a dry, dark area. Intended Use For in vitro laboratory analysis only. Caution Treat as hazardous substance. Use appropriate work practices when handling to avoid skin or eye contact, ingestion or inhalation of dust. Legal notice Neither NMI nor any person acting on NMI s behalf assumes any liability with respect to the use of, or for damages resulting from the use of, this reference material or the information contained in this certificate. Authorised by: Dr Stephen R. Davies, Team Leader, Chemical Reference Materials, NMI. Dated: 20 May, Characterisation data and property values specified in this report supersede those in all reports issued prior to 16 th July 2012 Page 4 of 4
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