Table 1. Signals Identified in Mass Spectra of Native Cannabis Extract (Prior to Decarboxylation Process) and the Corresponding Compoundsa.
| signal # | [M – H]− | [MH]+ | MW | retention time (min) | corresponding compound(s)27,28,32−39 | compound class |
|---|---|---|---|---|---|---|
| 1 | NA | 221.14 | 220.14 | 5–5.5 | β-caryophyllene oxide | sesquiterpene |
| 2 | NA | 251.23 | 250.23 | 1–1.5 | roughanic acid27 | fatty acids |
| 3 | NA | 277.27 | 276.27 | 0–0.5 | stearidonic acid32 | |
| 4 | NA | 279.30 | 278.30 | 0.5–1 | α-linolenic acid | |
| 5 | 301.15 | NA | 302.15 | 0–0.5 | quercetin | flavonols C1-cannabinoid acids |
| 4,5-dihydroxy-2,3,6-trimethoxy-9,10-dihydrophenanthrene33 | ||||||
| Δ9-tetrahydrocannabiorcolic acid | ||||||
| cannabigerol(*) | ||||||
| 9,10-dihydro-2,3,5,6-tetramethoxyphenanthrene-1,4-dione34 | ||||||
| cannabichromevarinic acid(*) | ||||||
| cannabidivarinic acid(*) | ||||||
| Δ9-tetrahydrocannabivarinic acid(*) | ||||||
| cannabielsoin(*) | ||||||
| 6 | NA | 315.33 | 314.33 | 1.5–2 | cannabicitran | neutral cannabinoids |
| Δ8-tetrahydrocannabinol | ||||||
| Δ9-tetrahydrocannabinol | ||||||
| cannabichromene | ||||||
| cannabidiol | ||||||
| cannabicyclol | ||||||
| 7 | 329.14 | NA | 330.14 | 1–1.5 | 9,10-dihydro-2,3,5,6-tetramethoxyphenanthrene-1,4-dione34 | C3-cannabinoid acids and neutral cannabinoid derivatives |
| cannabichromevarinic acid | ||||||
| cannabidivarinic acid | ||||||
| Δ9-tetrahydrocannabivarinic acid | ||||||
| cannabielsoin | ||||||
| 2-geranyl-5-hydroxy-3-n-pentyl-1,4-benzoquinone35 | ||||||
| 10α-hydroxy-Δ9,11-hexahydrocannabinol36 | ||||||
| 10α/β-hydroxy-Δ8-tetrahydrocannabinol36 | ||||||
| 3-hydroxy-Δ4,5-cannabichromene35 | ||||||
| 8α/β-hydroxy-Δ9-tetrahydrocannabinol36 | ||||||
| 9β,10β-epoxyhexahydrocannabinol36 | ||||||
| cannabicoumaronone34 | ||||||
| cannabigerol monomethylether | ||||||
| cannabitriol(*) | ||||||
| cannabichromenic acid(*) | ||||||
| cannabidiolic acid(*) | ||||||
| cannabicyclolic acid(*) | ||||||
| Δ9-tetrahydrocannabinolic acid(*) | ||||||
| 7R-cannabicoumaronic acid35(*) | ||||||
| 5-acetoxy-6-geranyl-3-n-pentyl-1,4-benzoquinone33(*) | ||||||
| cannabigerolic acid monomethyl ether(*) | ||||||
| 8 | 331.24 | NA | 332.24 | 1–1.5 | cannabichromanon | neutral cannabinoid derivatives |
| (±)-6,7-cis/trans-epoxycannabigerol37 | ||||||
| 7-hydroxycannabichromane35 | ||||||
| cannabigerolic acid(*) | ||||||
| cannabitriol(*) | ||||||
| 11-hydroxy-Δ9-tetrahydrocannabinolic acid A(*) | ||||||
| 4-acetoxy-2-geranyl-5-hydroxy-3-n-pentylphenol33(*) | ||||||
| 5-acetyl-4-hydroxycannabigerol(*) | ||||||
| 10-ethoxy-9-hydroxy-Δ6a-tetrahydrocannabinol(*) | ||||||
| 9 | NA | 341.37 | 340.37 | 1.5–2 | cannabichromenic acid(*) | C5-cannabinoid acid fragments |
| cannabidiolic acid(*) | ||||||
| cannabicyclolic acid(*) | ||||||
| Δ9-tetrahydrocannabinolic acid(*) | ||||||
| 10 | 343.17 | NA | 344.17 | 1–1.5 | C4-tetrahydrocannabinolic acid | C4-cannabinoid acids and C5-cannabinoid acid fragments |
| cannabigerolic acid(*) | ||||||
| cannabichromenic acid(*) | ||||||
| Δ9-tetrahydrocannabinolic acid(*) | ||||||
| cannabidiolic acid(*) | ||||||
| cannabicyclolic acid(*) | ||||||
| 11 | 357.20 | NA | 358.20 | 0.5–1 | cannabichromenic acid | C5-cannabinoid acids |
| cannabidiolic acid | ||||||
| cannabicyclolic acid | ||||||
| Δ9-tetrahydrocannabinolic acid | ||||||
| 4-acetoxy-2-geranyl-5-hydroxy-3-n-pentylphenol33(*) | ||||||
| 10-ethoxy-9-hydroxy-Δ6a-tetrahydrocannabino(*) | ||||||
| 12 | 371.16 | 373.34 | 372.25 | 1–1.5 | 7R-cannabicoumaronic acid35 | cannabinoid derivatives |
| Δ9-tetrahydrocannabinolic acid-A-8-one28 | ||||||
| 5-acetoxy-6-geranyl-3-n-pentyl-1,4-benzoquinone33 | ||||||
| 4-acetoxycannabichromene38 | ||||||
| 13 | 373.26 | NA | 374.26 | 1–1.5 | 11-hydroxy-Δ9-tetrahydrocannabinolic acid A | C5-cannabinoid acids and cannabinoid derivatives |
| α/β-cannabielsoic acid | ||||||
| 4-acetoxy-2-geranyl-5-hydroxy-3-n-pentylphenol33 | ||||||
| 10-ethoxy-9-hydroxy-Δ6a-tetrahydrocannabinol | ||||||
| 5-acetyl-4-hydroxycannabigerol35 | ||||||
| 5-methoxycannabigerolic acid37 | ||||||
| cannabigerolic acid monomethyl ether | ||||||
| 14 | 375.21 | NA | 376.21 | 1–1.5 | (±)-6,7-cis/trans-epoxycannabigerolic acid37 | cannabinoid acid derivatives |
| 15 | 389.25 | NA | 390.25 | 0.5–1 | 8b,11-bis-hydroxy-Δ9-tetrahydrocannabinolic acid | |
| 16 | 399.30 | NA | 400.30 | 2.5–3 | Δ9-tetrahydrocannabinolic acid + C2H2O | |
| 17 | 417.31 | NA | 418.31 | 2–2.5 | orientin(*) | flavone fragment |
| 18 | 457.08 | NA | 458.08 | 3–3.5 | acetyl stigmasterol34 | sterol |
| cannabisin A(*) | ||||||
| 19 | 473.50 | NA | 474.50 | 3–3.5 | cannabisin A(*) | lignanamide fragment |
| 20 | 493.32 | NA | 494.32 | 2–2.5 | 4-terpenyl-Δ9-tetrahydro cannabinolate39 | cannabinoid acid esters |
| α-terpenyl-Δ9-tetrahydro cannabinolate39 | ||||||
| bornyl/epi-bornyl-Δ9-tetrahydro cannabinolate39 | ||||||
| α/β-fenchyl-Δ9-tetrahydro cannabinolate39 | ||||||
| 21 | 509.45 | NA | 510.45 | 2–2.5 | chlorophyll (decarboxylated)29 | chlorophyll |
| 22 | 593.32 | NA | 594.32 | 3.5–4 | apigenin-6,8-di-C-β-d-glucopyranoside34 | flavone and lignanamide |
| cannabisin A |
a
Asterisks (*) indicate fragment ions instead of molecular ions for the corresponding signals.