JWH-019

Summary

JWH-019, a member of the naphthoylindole family, is recognized as an analgesic compound acting as a cannabinoid agonist at both CB1 and CB2 receptors. Notably, it is the N-hexyl homolog of the known synthetic cannabinoid JWH-018. In contrast to the butyl homolog, JWH-073, which exhibits significantly lower potency than JWH-018, the hexyl homolog, JWH-019, maintains a relatively high potency level. However, it’s noteworthy that extending the carbon chain by just one additional carbon, as seen in the heptyl homolog, JWH-020 leads to a considerable loss of activity.
This observation underscores the significance of the five-carbon pentyl chain as the optimal side chain length for CB1 binding in the naphthoylindole series, distinguishing it from classical cannabinoids where a seven-carbon heptyl chain results in the most potent compounds. This difference is believed to stem from a slight variation in the binding conformation adopted by naphthoylindole compounds compared to classical cannabinoids, providing valuable insights into the active site characteristics of CB1 and CB2 receptors.

Identifiers

IUPAC name
CAS Number	209414-08-4
ChemSpider	24598813
UNII	0Z73828O4J
CompTox Dashboard (EPA)	DTXSID70175118
Chemical and physical data
Formula	C25H25NO
Molar mass	355.481 g·mol−1

Legal status

China
In October 2015, China categorized JWH-019 as a controlled substance.
Poland
JWH-019 is designated as a controlled substance in Poland, falling under the category of I-N.
Sweden
The possession and use of JWH-019 is prohibited in Sweden.
United Kingdom
JWH-019 is classified as a Class B substance in the United Kingdom.
United States
JWH-019 is classified as a Schedule I controlled substance, subject to federal control in the United States.

FAQ

• What is JWH-019?
• JWH-019 is a chemical compound classified as a synthetic cannabinoid. It is part of the naphthoylindole family and is known for its activity as a cannabinoid agonist at both CB1 and CB2 receptors.
• How does JWH-019 differ from other synthetic cannabinoids?
• JWH-019 is the N-hexyl homolog of the more widely recognized synthetic cannabinoid, JWH-018. Unlike specific homologs like JWH-073, which are notably weaker than JWH-018, JWH-019 retains relatively high potency. However, extending the carbon chain by a single carbon atom to create the heptyl homolog, JWH-020 leads to a significant reduction in activity.
• Why is the pentyl chain length significant in the naphthoylindole series?
• The five-carbon pentyl chain has been identified as the optimal side chain length for CB1 binding within the naphthoylindole series. This differs from classical cannabinoids, where a seven-carbon heptyl chain produces the most potent compounds. This distinction provides valuable insights into the binding conformation of naphthoylindole compounds compared to classical cannabinoids.
• Is JWH-019 legal?
• The legal status of JWH-019 varies by country. It is crucial to check your local regulations and laws regarding its possession, use, and distribution. As of October 2015, it is classified as a controlled substance in several countries, including China, Poland, Sweden, the United Kingdom, and the United States.
• Is JWH-019 safe for consumption?
• The safety of JWH-019 for human consumption is not well-documented, and its use can pose health risks. Synthetic cannabinoids can have unpredictable effects, including adverse reactions. It is essential to exercise caution and follow relevant laws and regulations regarding its use.
• Is JWH-019 used for medicinal purposes?
• JWH-019 and other synthetic cannabinoids were not developed or approved for medicinal use. However, research into the potential therapeutic applications of cannabinoids is ongoing, particularly concerning pain management, inflammation, and various medical conditions.
• What research is available on JWH-019?
• Scientific research on JWH-019 has explored its pharmacological properties, metabolism, and potential effects. Researchers have studied its interaction with cannabinoid receptors and its impact on various physiological processes. However, the use and study of synthetic cannabinoids remain a subject of ongoing investigation.
• Is JWH-019 the same as natural cannabinoids like THC and CBD?
• No, JWH-019 is a synthetic cannabinoid, meaning it is chemically distinct from natural cannabinoids found in the cannabis plant, such as tetrahydrocannabinol (THC) and cannabidiol (CBD). While they may interact with the same receptors, synthetic cannabinoids have unique chemical structures.
• Are there known side effects or risks associated with JWH-019 use?
• The use of synthetic cannabinoids, including JWH-019, can be associated with a range of side effects and health risks, including but not limited to anxiety, paranoia, hallucinations, rapid heartbeat, and nausea. Additionally, the long-term effects and safety profile of these substances are not well understood.
• Where can I find more information about JWH-019?
• For comprehensive and up-to-date information on JWH-019, it is advisable to consult scientific publications, government regulatory agencies, and reputable sources in your region. Additionally, consider seeking guidance from healthcare professionals if you have specific health-related concerns or questions.

References

1. “Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii ( Dz.U. 2011 nr 105 poz. 614 )” is a legislative act in Poland that pertains to amendments in the law concerning the combat of drug addiction. It has significant implications for the regulation of substances.
2. Aung MM, Griffin G, Huffman JW, Wu M, Keel C, Yang B, et al. (August 2000) conducted research on the influence of the N-1 alkyl chain length of cannabimimetic indoles on CB1 and CB2 receptor binding. Their findings contribute to our understanding of the pharmacology of these compounds.
3. Poso A, Huffman JW (January 2008) delved into the structural determinants of CB2-selective ligands targeting the cannabinoid CB2 receptor. This research is instrumental in the development of selective CB2 agonists.
4. Ashton JC, Wright JL, McPartland JM, Tyndall JD (2008) explored cannabinoid CB1 and CB2 receptor ligand specificity and the development of CB2-selective agonists. Their work sheds light on the selectivity of compounds for specific cannabinoid receptors.
5. “关于印发《非药用类麻醉药品和精神药品列管办法》的通知” (in Chinese) is a notification from the China Food and Drug Administration dated 27 September 2015. It provides information about the regulation and control of non-medicinal narcotic drugs and psychotropic substances in China.
6. The United States Drug Enforcement Administration (DEA) maintains a list of controlled substances, providing essential information about substances regulated by federal law in the United States.