Investigation of the transformation of 11-nor-9-carboxy-Δ(9)-tetrahydrocannabinol during water chlorination by liquid chromatography-quadrupole-time-of-flight-mass spectrometry
Copyright © 2013 Elsevier B.V. All rights reserved..
The stability of the main metabolite of cannabis, (±)-11-nor-9-carboxy-Δ(9)-tetrahydrocannabinol (THCCOOH), during water chlorination has been investigated. THCCOOH was degraded in few seconds following a pseudo-first order kinetics. Sample pH turned out to be a significant factor, decreasing THCCOOH half-life with an increase in its values. Seven by-products could be positively identified from accurate mass measurements: three compounds resulted from electrophilic substitutions of hydrogen per chlorine (or bromine) in the aromatic ring, whereas the formation of the remaining four involved additional reactions in the C-C double bond (hydration and halogenation). The software predicted toxicity of these products towards Daphnia magna indicates that they are expected to have toxicity values similar or higher than its precursor compound. Experiments conducted with diluted urine showed that THCCOOH was stable in this matrix, probably due to a rapid and complete reaction between chlorine and other organic constituents already present in the samples. In real surface waters, the extent of the reaction was also affected by the organic matter content, and so THCCOOH was rapidly degraded in samples scarcely affected by human activities, being more stable in waters with a higher level of pollution.
| Medienart: |
E-Artikel |
|---|
| Erscheinungsjahr: |
2013 |
|---|---|
| Erschienen: |
2013 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:261 |
|---|---|
| Enthalten in: |
Journal of hazardous materials - 261(2013) vom: 15. Okt., Seite 628-36 |
| Sprache: |
Englisch |
|---|
| Beteiligte Personen: |
González-Mariño, Iria [VerfasserIn] |
|---|
| Links: |
|---|
| Anmerkungen: |
Date Completed 03.06.2014 Date Revised 19.11.2015 published: Print-Electronic Citation Status MEDLINE |
|---|
| doi: |
10.1016/j.jhazmat.2013.08.006 |
|---|
| funding: |
|
|---|---|
| Förderinstitution / Projekttitel: |
|
| PPN (Katalog-ID): |
NLM230494803 |
|---|
| LEADER | 01000naa a22002652 4500 | ||
|---|---|---|---|
| 001 | NLM230494803 | ||
| 003 | DE-627 | ||
| 005 | 20231224084545.0 | ||
| 007 | cr uuu---uuuuu | ||
| 008 | 231224s2013 xx |||||o 00| ||eng c | ||
| 024 | 7 | |a 10.1016/j.jhazmat.2013.08.006 |2 doi | |
| 028 | 5 | 2 | |a pubmed24n0768.xml |
| 035 | |a (DE-627)NLM230494803 | ||
| 035 | |a (NLM)23995559 | ||
| 035 | |a (PII)S0304-3894(13)00562-1 | ||
| 040 | |a DE-627 |b ger |c DE-627 |e rakwb | ||
| 041 | |a eng | ||
| 100 | 1 | |a González-Mariño, Iria |e verfasserin |4 aut | |
| 245 | 1 | 0 | |a Investigation of the transformation of 11-nor-9-carboxy-Δ(9)-tetrahydrocannabinol during water chlorination by liquid chromatography-quadrupole-time-of-flight-mass spectrometry |
| 264 | 1 | |c 2013 | |
| 336 | |a Text |b txt |2 rdacontent | ||
| 337 | |a ƒaComputermedien |b c |2 rdamedia | ||
| 338 | |a ƒa Online-Ressource |b cr |2 rdacarrier | ||
| 500 | |a Date Completed 03.06.2014 | ||
| 500 | |a Date Revised 19.11.2015 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Copyright © 2013 Elsevier B.V. All rights reserved. | ||
| 520 | |a The stability of the main metabolite of cannabis, (±)-11-nor-9-carboxy-Δ(9)-tetrahydrocannabinol (THCCOOH), during water chlorination has been investigated. THCCOOH was degraded in few seconds following a pseudo-first order kinetics. Sample pH turned out to be a significant factor, decreasing THCCOOH half-life with an increase in its values. Seven by-products could be positively identified from accurate mass measurements: three compounds resulted from electrophilic substitutions of hydrogen per chlorine (or bromine) in the aromatic ring, whereas the formation of the remaining four involved additional reactions in the C-C double bond (hydration and halogenation). The software predicted toxicity of these products towards Daphnia magna indicates that they are expected to have toxicity values similar or higher than its precursor compound. Experiments conducted with diluted urine showed that THCCOOH was stable in this matrix, probably due to a rapid and complete reaction between chlorine and other organic constituents already present in the samples. In real surface waters, the extent of the reaction was also affected by the organic matter content, and so THCCOOH was rapidly degraded in samples scarcely affected by human activities, being more stable in waters with a higher level of pollution | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Research Support, Non-U.S. Gov't | |
| 650 | 4 | |a 11-Nor-9-carboxy-Δ(9)-tetrahydrocannabinol (THCCOOH) | |
| 650 | 4 | |a Cannabis | |
| 650 | 4 | |a Chlorination | |
| 650 | 4 | |a Liquid chromatography–mass spectrometry (LC–MS) | |
| 650 | 4 | |a Time-of-flight (TOF) | |
| 650 | 4 | |a Transformation products | |
| 650 | 7 | |a Water Pollutants, Chemical |2 NLM | |
| 650 | 7 | |a Chlorine |2 NLM | |
| 650 | 7 | |a 4R7X1O2820 |2 NLM | |
| 650 | 7 | |a 11-nor-delta(9)-tetrahydrocannabinol-9-carboxylic acid |2 NLM | |
| 650 | 7 | |a 4TPC9E4A32 |2 NLM | |
| 650 | 7 | |a Dronabinol |2 NLM | |
| 650 | 7 | |a 7J8897W37S |2 NLM | |
| 700 | 1 | |a Rodríguez, Isaac |e verfasserin |4 aut | |
| 700 | 1 | |a Quintana, José Benito |e verfasserin |4 aut | |
| 700 | 1 | |a Cela, Rafael |e verfasserin |4 aut | |
| 773 | 0 | 8 | |i Enthalten in |t Journal of hazardous materials |d 1998 |g 261(2013) vom: 15. Okt., Seite 628-36 |w (DE-627)NLM093662688 |x 1873-3336 |7 nnns |
| 773 | 1 | 8 | |g volume:261 |g year:2013 |g day:15 |g month:10 |g pages:628-36 |
| 856 | 4 | 0 | |u http://dx.doi.org/10.1016/j.jhazmat.2013.08.006 |3 Volltext |
| 912 | |a GBV_USEFLAG_A | ||
| 912 | |a GBV_NLM | ||
| 951 | |a AR | ||
| 952 | |d 261 |j 2013 |b 15 |c 10 |h 628-36 | ||