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Chlorination Kinetics of 11-Nor-9-carboxy-Δ9-tetrahydrocannabinol: Effects of pH and Humic Acid.

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Title: Chlorination Kinetics of 11-Nor-9-carboxy-Δ9-tetrahydrocannabinol: Effects of pH and Humic Acid.
Authors: Mackie, Allison L.1, Park, Yu Ri1, Gagnon, Graham A.1 graham.gagnon@dal.ca.
Source: Environmental Science & Technology. 9/19/2017, Vol. 51 Issue 18, p10711-10717. 7p.
Subjects: Psychiatric drugs, Tetrahydrocannabinol, Chlorination, Chemical kinetics, Humic acid, pH effect
Abstract: The main psychoactive compound in marijuana, Δ9-tetrahydrocannabinol (THC), and its metabolites are emerging organic contaminants that have been detected in waste and surface waters. As legalization of marijuana for medical and recreational use continues, the effects of increased use and potency of marijuana on water and wastewater treatment processes and the environment should be considered. This study examined degradation kinetics of the main urinary metabolite of THC, 11-nor-9-carboxy-Δ9-tetrahydrocannabinol (THC-COOH) with chlorine. THC-COOH was rapidly removed from both deionized (DI) water at pH 5.6 ± 0.2 and Suwannee River humic acid (SRHA) at pH 5.1 ± 0.2 using low doses of chlorine (0.1 to 0.50 mg free Cl2/L), with half-lives calculated from second-order kinetics constants (k2) of 8 s for DI and 42 s for DI with SRHA. Kinetic rates increased with an increase in pH from 5 to 9 in both DI water and SRHA and no interference from phosphate was observed. The chlorination pathway of electrophilic substitution of Cl at the ortho or para position of the phenol structure of THC-COOH was confirmed by detection of monochlorinated byproduct fragmentation ions using flow injection analysis with orbitrap mass spectrometry. [ABSTRACT FROM AUTHOR]
Copyright of Environmental Science & Technology is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Database: Engineering Source
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  Data: <searchLink fieldCode="AR" term="%22Mackie%2C+Allison+L%2E%22">Mackie, Allison L.</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Park%2C+Yu+Ri%22">Park, Yu Ri</searchLink><relatesTo>1</relatesTo><br /><searchLink fieldCode="AR" term="%22Gagnon%2C+Graham+A%2E%22">Gagnon, Graham A.</searchLink><relatesTo>1</relatesTo><i> graham.gagnon@dal.ca.</i>
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  Data: <searchLink fieldCode="JN" term="%22Environmental+Science+%26+Technology%22">Environmental Science & Technology</searchLink>. 9/19/2017, Vol. 51 Issue 18, p10711-10717. 7p.
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  Data: <searchLink fieldCode="DE" term="%22Psychiatric+drugs%22">Psychiatric drugs</searchLink><br /><searchLink fieldCode="DE" term="%22Tetrahydrocannabinol%22">Tetrahydrocannabinol</searchLink><br /><searchLink fieldCode="DE" term="%22Chlorination%22">Chlorination</searchLink><br /><searchLink fieldCode="DE" term="%22Chemical+kinetics%22">Chemical kinetics</searchLink><br /><searchLink fieldCode="DE" term="%22Humic+acid%22">Humic acid</searchLink><br /><searchLink fieldCode="DE" term="%22pH+effect%22">pH effect</searchLink>
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  Data: The main psychoactive compound in marijuana, Δ9-tetrahydrocannabinol (THC), and its metabolites are emerging organic contaminants that have been detected in waste and surface waters. As legalization of marijuana for medical and recreational use continues, the effects of increased use and potency of marijuana on water and wastewater treatment processes and the environment should be considered. This study examined degradation kinetics of the main urinary metabolite of THC, 11-nor-9-carboxy-Δ9-tetrahydrocannabinol (THC-COOH) with chlorine. THC-COOH was rapidly removed from both deionized (DI) water at pH 5.6 ± 0.2 and Suwannee River humic acid (SRHA) at pH 5.1 ± 0.2 using low doses of chlorine (0.1 to 0.50 mg free Cl2/L), with half-lives calculated from second-order kinetics constants (k2) of 8 s for DI and 42 s for DI with SRHA. Kinetic rates increased with an increase in pH from 5 to 9 in both DI water and SRHA and no interference from phosphate was observed. The chlorination pathway of electrophilic substitution of Cl at the ortho or para position of the phenol structure of THC-COOH was confirmed by detection of monochlorinated byproduct fragmentation ions using flow injection analysis with orbitrap mass spectrometry. [ABSTRACT FROM AUTHOR]
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  Data: <i>Copyright of Environmental Science & Technology is the property of American Chemical Society and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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        Value: 10.1021/acs.est.7b02234
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      – Code: eng
        Text: English
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      – SubjectFull: Psychiatric drugs
        Type: general
      – SubjectFull: Tetrahydrocannabinol
        Type: general
      – SubjectFull: Chlorination
        Type: general
      – SubjectFull: Chemical kinetics
        Type: general
      – SubjectFull: Humic acid
        Type: general
      – SubjectFull: pH effect
        Type: general
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      – TitleFull: Chlorination Kinetics of 11-Nor-9-carboxy-Δ9-tetrahydrocannabinol: Effects of pH and Humic Acid.
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              Text: 9/19/2017
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