∆9-TETRAHYDROCANNABINOL Methanol Solution

Product Number T 4764 Synonyms Tetrahydro-6,6,9-trimethyl-3-pentyl- 6H-dibenzo[b,d]pyran-1-ol; Lot Number 91K8801 ∆1-Tetrahydrocannabinol; ∆9-THC; ∆1-THC CAS Number [1972-08-3] Stability If stored at 2-8°C in an air tight container, Concentration 1.05 mg ∆9-Tetrahydrocannabinol/mL protected from light, decomposition of the GC grade methanol (conc. verified product is less than 1% in 24 months. After by HPLC) opening, concentration may change due to loss of solvent. Molecular Formula C21H30O2 Expiration Date May 2004 Molecular Weight 314.5 Storage 2-8°C; After opening, transfer contents to DEA Class Exempt preparation of Class I small vial provided for your convenience.

High Pressure Liquid Chromatography

Column C-18: 5 micron, 4.6 x 25 cm (Supelco 58298-C46) Mobile Phase 80 % Methanol / 20 % 18 MΩ water Gradient isocratic Flow Rate 1.0 mL/min. Temp ambient Detector UV @ 210 nm

5 10 15 20 25 30 Time (min.) Perkin-Elmer LC-4 with Hewlett-Packard 3365 Series II Chemstation

FT-IR

100

% 80 T r a n 60 s m i t 40 t a n c e 20 KBr 4000 3600 3200 2800 2400 2000 1600 1200 800 400

Wavenumbers (cm-1) Mattson Galaxy 3020 FT-IR ∆9-TETRAHYDROCANNABINOL CH3

Methanol Solution OH Product Number T 4764 Lot Number 91K8801 H C 3 H C O CH (C H ) CH 3 2 2 3 3

Ultraviolet Spectrum Capillary Gas Chromatography

Peak 276.5 nm Column Supelco SPB-1 (Cat. No. 2-4162) I.D. 0.20 mm Length 15 m Film Thickness 0.20 µm Absorbance 0.399 Oven Temperature 50°C (2 min.), then 15°/min. to 300°C, Solvent Methanol hold 11 min. Injector Temperature 250°C, Split Dilution 1 : 9 (v/v) Detector Hewlett-Packard 5971 Mass Selective Detector (70 eV, 40-500 m/z)

1.0

0.9

0.8

A 0.7 b s 0.6 o r b 0.5 a n 0.4 c e 0.3

0.2

0.1

0 200 240 280 320 220 260 300 5.00 10.00 15.00 20.00 25.00 Wavelength (nm) Time (min.)

Bio-Tek Uvikon XL Hewlett-Packard 5890

70 eV Electron Ionization Mass Spectrum

Abundance 299 35000 231 314 30000

25000

20000 271

15000 243 258 10000 41 91 174 5000 81 115 193 55 67 128 147 187 217 161 285 0 40 60 80 100 120 140 160 180 200 220 240 260 280 300 m/z

Hewlett-Packard 5890 Series II Gas Chromatograph Hewlett-Packard 5971 Mass Selective Detector Hewlett-Packard G1034C MS ChemStation (HP-DOS series)

T 4764/91K8801/09/21/01 This product is not for in vitro diagnostic procedures. For R&D use only. Not for drug, household or other uses. Sigma brand products are sold through Sigma-Aldrich, Inc. Sigma-Aldrich, Inc. warrants that its products conform to the information contained in this and other Sigma-Aldrich publications. Purchaser must determine the suitability of the product(s) for their particular use. Additional terms and conditions may apply. Please see reverse side of the invoice or packing slip.