Since 2004, a number of “herbal blends” containing synthetic cannabinoid analogues have appeared in the market, as a form of “legal” alternatives to Cannabis. These products are available online through the “e-commerce” and in “smart shops” under several forms and various brand names. A particular warning related to the diffusion of synthetic cannabinoids is based on one hand on their high toxicological potential, and on the other hand on the insensitivity of the current screening tests for cannabis towards these molecules. Moreover, because of their recent introduction, the literature regarding these compounds is still limited. In particular any experimental information on their octanol/water partition coefficient (logP) values is still lacking. Indeed, hydrophobicity value is an important parameter to investigate drug absorption, bioavailability and metabolism of molecules, as well as their toxicity. As a measure of molecular hydrophobicity, the logarithm of the partition coefficient between 1-octanol and water (logP) is widely used. The aim of the present study was to calculate the LogP of synthetic cannabinoids by using micellar electrokinetic chromatography (MEKC) with UV detection. Samples were analyzed using a fused silica capillary (30 mm x 40 cm) and a 25 mM sodium borate buffer pH 8, containing30 mMSDS and n-propanol 20%. After having constructed a calibration line using 10 appropriate standards with known LogP, an EOF marker and a micelle marker, a good correlation was found between the MEKC retention data of further 5 compounds with known LogP. The same calibration line was used to calculate the unknown LogP of the new synthetic cannabinoids, namely JWH-200, AM-694, JWH-250, JWH-073, JWH-015, JWH-018, JWH-081, JWH-122, JWH-019, JWH-210. The resulting Log P were in the range from 2.9 to 5.15. An acceptable agreement was found between the experimental data and a few LogP values calculated with XLogP3-AA reported in the literature.

Calculation of LogP based on migration data in MEKC: application to the new synthetic cannabinoids.

BERTASO, Anna;GOTTARDO, Rossella;Musile, Giacomo;SORIO, DANIELA;TAGLIARO, Franco
2012

Abstract

Since 2004, a number of “herbal blends” containing synthetic cannabinoid analogues have appeared in the market, as a form of “legal” alternatives to Cannabis. These products are available online through the “e-commerce” and in “smart shops” under several forms and various brand names. A particular warning related to the diffusion of synthetic cannabinoids is based on one hand on their high toxicological potential, and on the other hand on the insensitivity of the current screening tests for cannabis towards these molecules. Moreover, because of their recent introduction, the literature regarding these compounds is still limited. In particular any experimental information on their octanol/water partition coefficient (logP) values is still lacking. Indeed, hydrophobicity value is an important parameter to investigate drug absorption, bioavailability and metabolism of molecules, as well as their toxicity. As a measure of molecular hydrophobicity, the logarithm of the partition coefficient between 1-octanol and water (logP) is widely used. The aim of the present study was to calculate the LogP of synthetic cannabinoids by using micellar electrokinetic chromatography (MEKC) with UV detection. Samples were analyzed using a fused silica capillary (30 mm x 40 cm) and a 25 mM sodium borate buffer pH 8, containing30 mMSDS and n-propanol 20%. After having constructed a calibration line using 10 appropriate standards with known LogP, an EOF marker and a micelle marker, a good correlation was found between the MEKC retention data of further 5 compounds with known LogP. The same calibration line was used to calculate the unknown LogP of the new synthetic cannabinoids, namely JWH-200, AM-694, JWH-250, JWH-073, JWH-015, JWH-018, JWH-081, JWH-122, JWH-019, JWH-210. The resulting Log P were in the range from 2.9 to 5.15. An acceptable agreement was found between the experimental data and a few LogP values calculated with XLogP3-AA reported in the literature.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11562/509751
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