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Posts Tagged ‘pharmacokinetics’

Understanding JWH-018

Tuesday, May 18th, 2010

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JWH-018 is one of several hundred JWH compounds developed over the last few years by John W. Huffman (JWH), organic chemist, as part of research on analogues and metabolites of THC, the active ingredient of naturally sourced marijuana plant (10). Intended exclusively for purposes of scientific purposes, JWH-018 has never been intended for human consumption, let alone recreational use. While there are anywhere from 100 to 300 various JWH compounds, JWH-018 has yielded the highest interest due to its active group functional similarity to THC.

Introduction of marijuana-specific treatment programs (11) have opened the door for a cheaper more accessible alternative, JWH-018, a synthetic marijuana. While it is easy to assume that JWH-018 would act the same as naturally sourced marihuana, the reality is that they are quite different. In many aspects JWH-018 is more potent and inherently more dangerous to human body. To fully understand JWH-018, it is necessary to consider certain aspects of its chemical characteristics, pharmacology, pharmacokinetics, metabolism and addiction potential.

Chemical Structure

JWH-018

JWH-018, also known as K2, fake weed, synthetic marihuana, “spice” and  1-pentyl-3-(1-naphthoyl) indole is a synthetic cannabinoid from aminoalkylindole family, covered under US patent  #7241799(4). It acts as CB1 and CB2, receptor agonist, with partial CB2 selectivity.[1][2] . As both CB1 and CB2 are involved neurotransmitter regulation, JWH-018 has a significant impact on a wide range of neural functions.  Four to five times more powerful than weed, it is a lipid-soluble, non-polar, small molecule (9), with physical appearance of a white crystalline powder with pharmacological resemblance but no chemical relation to tetrahydrocannabinols (THC), an active ingredient of Cannabis sativa L. (marihuana), nor to other cannabinoids from cannabis plant (5). Consequently JWH-018 is not categorized as a THC substance (6).

References

1)     Influence of the N-1 alkyl chain length of cannabimimetic indoles upon CB1 and CB2 receptor binding, Aung, M. M.; et al. (2000), Drug and Alcohol Dependence 60 (2): 133–140, doi:10.1016/S0376-8716(99)00152-0.

2)     Cannabimimetic indole derivatives, US6,900,236 (PDF version) (2005-05-31) Alexandros Makriyannis, Hongfeng Deng

3)     JWH-018 CYP450 Inhibition. Raw data. Netherlands. 18 Dec. 2008

4)     Cannabimimetic indole derivatives, Makriyannis, Alexandros, and Hongfeng Deng. University of Connecticut, assignee, Patent 7241799. 2007

5) http://www.babelation.com/content/jwh-018synthetic-cannabinoid-agonist-synthetic-cannabis-found-be-4-5-times-stronger-then-mar.

6) JWH-018, 1-Pentyl-3-(1-naphthoyl)indole, Purported Ingredient of “Spice”, July 2009, http://www.deadiversion.usdoj.gov/drugs_concern/spice/spice_jwh018.htm)

9)      Understanding the Spice Phenomenon, EMCDDA, EMCDDA 2009  Thematic paper, 2009

10)     Synthesis of Cannabimimetic Indoles, John W. Huffman, 2008

11)     Effects of THC and lofexidine in a human laboratory model of marijuana withdrawal and relapse, Margaret Haney & Carl L. Hart & Suzanne K. Vosburg & Sandra D. Comer & Stephanie Collins Reed & Richard W. Foltin, 7 November 2007



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