JWH-007

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Summary

JWH-007, a member of the naphthoylindole family, is a chemical compound primarily recognized for its analgesic properties. It functions as a cannabinoid agonist, engaging both CB1 and CB2 receptors. This compound was initially documented in 1994, and its discovery is attributed to a group led by the renowned cannabinoid chemist John W. Huffman.
This compound is notable for being one of the most active substances among the first N-alkyl naphthoylindoles that Huffman’s team identified. It came several years after the N-morpholinyl ethyl compounds pravadoline (WIN 48,098), JWH-200 (WIN 55,225), and WIN 55,212-2 were first described by the Sterling Winthrop group within the same chemical family.
Huffman’s research also revealed the activity of several other N-alkyl substituents, such as n-butyl, n-hexyl, 2-heptyl, and cyclohexylethyl groups. However, it was later determined that a 2-methyl group on the indole ring is not essential for CB1 binding. It tends to enhance the affinity for CB2 receptors instead.
As a result, the 2-desmethyl derivative of JWH-007, known as JWH-018, exhibits a slightly higher binding affinity for CB1. It displays optimal binding at 9.00 nM at CB1 and 2.94 nM at CB2, while JWH-007 itself shows an optimum binding of 9.50 nM at CB1 and 2.94 nM at CB2.
It is important to note that another drug with a similar name, JHW-007 (not JWH), is a cocaine analogue and atypical dopamine reuptake inhibitor, which is distinct from and unrelated to JWH-007.

Identifiers
IUPAC name
CAS Number155471-10-6 
PubChem CID10360860
ChemSpider8536309
UNII5IQ75333OM
CompTox Dashboard (EPA)DTXSID20165903
Chemical and physical data
FormulaC25H25NO
Molar mass355.481 g·mol−1

Legal status

In the United States, substances that activate CB1 receptors and belong to the 3-(1-naphthyl)indole class, like JWH-007, are classified as Schedule I Controlled Substances.
In Sweden, JWH-007 was prohibited on October 1, 2010, following its detection as an ingredient in “herbal” synthetic cannabis products.
Since August 2010, JWH-007 has been illegal in Poland.
Additionally, as of October 2015, JWH-007 is designated as a controlled substance in China.

FAQ

  • What is JWH-007?
  • JWH-007 is a chemical compound from the 3-(1-naphthyl)indole class, recognized for its cannabinoid receptor agonist properties.
  • Is JWH-007 legal in the United States?
  • No, JWH-007, like other CB1 receptor agonists in the 3-(1-naphthyl)indole class, is classified as a Schedule I Controlled Substance in the United States, making it illegal.
  • Why was JWH-007 banned in Sweden?
  • In Sweden, JWH-007 was prohibited on October 1, 2010, due to its identification as an ingredient in “herbal” synthetic cannabis products.
  • Is JWH-007 illegal in Poland?
  • Yes, JWH-007 has been illegal in Poland since August 2010.
  • When did JWH-007 become a controlled substance in China?
  • JWH-007 was designated as a controlled substance in China as of October 2015.
  • Are there any potential medical uses for JWH-007?
  • JWH-007 is not associated with medical applications and is primarily known for its presence in synthetic substances with potential psychoactive effects.
  • What are the potential effects of JWH-007?
  • Similar to other synthetic cannabinoids, JWH-007 may produce effects that influence mood and perception, but these effects can vary and may come with health risks.
  • Is JWH-007 safe for use?
  • The safety of JWH-007 is a subject of concern, and its unregulated nature can lead to unpredictable health risks. It is not approved for medical or recreational use.
  • Where can I find more information about JWH-007?
  • To learn more about JWH-007, it is advisable to consult reliable sources and adhere to local laws and regulations, which may vary by jurisdiction.

References

  1. Huffman JW, Dai D, Martin BR, Compton DR (1994): In 1994, a pivotal study by Huffman and colleagues explored the design, synthesis, and pharmacology of cannabimimetic indoles. This research was published in the Bioorganic & Medicinal Chemistry Letters, Volume 4, Issue 4.
  2. Pertwee RG, Griffin G, Lainton JA, Huffman JW (September 1995): In September 1995, Pertwee, Griffin, Lainton, and Huffman conducted a pharmacological characterization of three novel cannabinoid receptor agonists in the mouse isolated vas deferens. The results were published in the European Journal of Pharmacology, Volume 284, Issue 3.
  3. Compton DR, Gold LH, Ward SJ, Balster RL, Martin BR (December 1992): In December 1992, Compton, Gold, Ward, Balster, and Martin investigated the cannabimimetic activity of aminoalkylindole analogs. This work examined a class of compounds structurally distinct from delta 9-tetrahydrocannabinol and was documented in The Journal of Pharmacology and Experimental Therapeutics, Volume 263, Issue 3.
  4. Huffman JW, Zengin G, Wu MJ, Lu J, Hynd G, Bushell K, et al. (January 2005): In January 2005, Huffman and his team delved into the structure-activity relationships for 1-alkyl-3-(1-naphthoyl)indoles at the cannabinoid CB(1) and CB(2) receptors, specifically investigating steric and electronic effects of naphthoyl substituents. The results led to the development of new highly selective CB(2) receptor agonists, as published in Bioorganic & Medicinal Chemistry, Volume 13, Issue 1.
  5. Huffman JW, Padgett LW (2005): In 2005, Huffman and Padgett provided insights into recent developments in the medicinal chemistry of cannabimimetic indoles, pyrroles, and indenes. This research was published in Current Medicinal Chemistry, Volume 12, Issue 12.
  6. Aung MM, Griffin G, Huffman JW, Wu M, Keel C, Yang B, et al. (August 2000): In August 2000, Aung and colleagues explored the influence of the N-1 alkyl chain length of cannabimimetic indoles on CB(1) and CB(2) receptor binding. Their findings were published in Drug and Alcohol Dependence, Volume 60, Issue 2.
  7. Rothman RB, Baumann MH, Prisinzano TE, Newman AH (January 2008): In January 2008, Rothman and his team examined dopamine transport inhibitors based on GBR12909 and benztropine as potential medications to treat cocaine addiction. Their research was published in Biochemical Pharmacology, Volume 75, Issue 1.
  8. Velázquez-Sánchez C, García-Verdugo JM, Murga J, Canales JJ (July 2013): In July 2013, Velázquez-Sánchez and colleagues investigated the impact of the atypical dopamine transport inhibitor, JHW 007, on amphetamine-induced sensitization and synaptic reorganization within the nucleus accumbens. This research was published in Progress in Neuro-Psychopharmacology & Biological Psychiatry, Volume 44.
  9. 21 U.S.C. § 812: The United States Code (21 U.S.C.) in Section 812 outlines the Schedules of controlled substances, providing the legal framework for regulating various substances.
  10. Swedish Code of Statutes Regulation (2010:1086): This regulation in Sweden, specifically Swedish Code of Statutes Regulation (2010:1086), played a role in the prohibition of certain substances, including JWH-007.
  11. “Ustawa z dnia 15 kwietnia 2011 r. o zmianie ustawy o przeciwdziałaniu narkomanii”: This is the Polish law enacted on April 15, 2011, concerning amendments to the Act on Counteracting Drug Addiction. It influenced the legal status of substances like JWH-007 in Poland.
  12. “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)”: This Chinese notification from the China Food and Drug Administration, dated September 27, 2015, discusses regulations concerning non-medicinal narcotic drugs and psychotropic drugs, with an archived version available until October 1, 2015.

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