Powered by OpenAIRE graph
Found an issue? Give us feedback
image/svg+xml Jakob Voss, based on art designer at PLoS, modified by Wikipedia users Nina and Beao Closed Access logo, derived from PLoS Open Access logo. This version with transparent background. http://commons.wikimedia.org/wiki/File:Closed_Access_logo_transparent.svg Jakob Voss, based on art designer at PLoS, modified by Wikipedia users Nina and Beao Journal of Pharmaceu...arrow_drop_down
image/svg+xml Jakob Voss, based on art designer at PLoS, modified by Wikipedia users Nina and Beao Closed Access logo, derived from PLoS Open Access logo. This version with transparent background. http://commons.wikimedia.org/wiki/File:Closed_Access_logo_transparent.svg Jakob Voss, based on art designer at PLoS, modified by Wikipedia users Nina and Beao
Journal of Pharmaceutical Sciences
Article . 1974 . Peer-reviewed
License: Elsevier TDM
Data sources: Crossref
versions View all 2 versions
addClaim

Stability of Tetrahydrocannabinols I

Authors: E R, Garrett; J, Tsau;

Stability of Tetrahydrocannabinols I

Abstract

Δ9-Tetrahydrocannabinol, as monitored by flame-ionization GLC at various temperatures, degrades by a biphasic semilogarithmic curve with time in acidic aqueous solutions (<1 mg/ liter) below pH 4 to GLC-observable products with separate retention times and the degradations are specific hydrogen-ion catalyzed. The products are considered as Δ8-tetrahydrocannabinol, P1, P2, and P3 and can be observed and isolated by TLC. These products do not appear above pH 4 in the neutral region, and these degradations are primarily first order, are not biphasic, and are pH independent. The half-life of Δ9-tetrahydrocannabinol is about 15 min at 37° and pH 1, typical stomach conditions. The product P1 may give rise to cannabinol by the GLC and TLC procedures since the IR, UV, TLC, NMR, and GLC of thin-layer chromatographed P1 and cannabinol are coincident, but chloroform extracts do not show the higher absorbances expected if the product that forms in solution to give P1 is cannabinol. The products P2 and P3, isolated by TLC, are consistent with the expected properties of Δ9-hydroxycannabidiol and 9-hydroxycannabinol, respectively, by IR, UV, NMR, and mass spectroscopy. The final amounts of Δ8-tetrahydrocannabinol, P1, P2, and P3 are in a constant ratio independent of pH below pH 4. Δ9-Tetrahydrocannabinol, as monitored by flame-ionization GLC, degrades solely by a first-order process to an equilibrium with P2 and Pa at acidic pH values and the process is specific hydrogen-ion catalyzed. The equilibrium appears to be independent of pH below pH 4 and is the same when TLC-isolated P2 or P3 is used as the starting material. It follows that the acidcatalyzed isolated double-bond migration favors Δ8-tetrahydrocannabinol over the Δ9 compound, and it is most probable that the equilibrating P2 and P3 are results of water addition to the isolated double bond and ether solvolysis. The product that gives rise to the P1 retention time that ultimately gives cannabinol is structurally indeterminate at present.

Related Organizations
Keywords

Chromatography, Gas, Magnetic Resonance Spectroscopy, Spectrophotometry, Infrared, Temperature, Hydrogen-Ion Concentration, Kinetics, Drug Stability, Spectrophotometry, Ultraviolet, Carbon Radioisotopes, Chromatography, Thin Layer, Dronabinol, Cannabis

  • BIP!
    Impact byBIP!
    selected citations
    These citations are derived from selected sources.
    This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
    30
    popularity
    This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
    Top 10%
    influence
    This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
    Top 10%
    impulse
    This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
    Top 10%
Powered by OpenAIRE graph
Found an issue? Give us feedback
selected citations
These citations are derived from selected sources.
This is an alternative to the "Influence" indicator, which also reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Citations provided by BIP!
popularity
This indicator reflects the "current" impact/attention (the "hype") of an article in the research community at large, based on the underlying citation network.
BIP!Popularity provided by BIP!
influence
This indicator reflects the overall/total impact of an article in the research community at large, based on the underlying citation network (diachronically).
BIP!Influence provided by BIP!
impulse
This indicator reflects the initial momentum of an article directly after its publication, based on the underlying citation network.
BIP!Impulse provided by BIP!
30
Top 10%
Top 10%
Top 10%
Upload OA version
Are you the author of this publication? Upload your Open Access version to Zenodo!
It’s fast and easy, just two clicks!