MDA-19

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Summary

MDA-19 also recognized as BZO-HEXOXIZID, is a potent and highly selective agonist specifically designed for the cannabinoid receptor CB2. It maintains reasonable selectivity over the psychoactive CB1 receptor, although variations are observed among different species. In animal studies, MDA-19 has shown effectiveness in addressing neuropathic pain, with no significant impact on rat locomotor activity noted in a particular study. It’s important to note that the pharmacological interaction of MDA-19 with rat cannabinoid receptors differs from its interaction with human cannabinoid receptors, as it exhibits a 6.9 times higher binding affinity for human CB1 receptors than rat CB1 receptors.

Identifiers
IUPAC name
CAS Number1048973-47-2 
1104302-26-2 (alternative)
PubChem CID25034599
ChemSpider24689676 
UNIIX83OI5CX2U
Chemical and physical data
FormulaC21H23N3O2
Molar mass349.434 g·mol−1

Pharmacology

MDA-19 demonstrates distinct binding properties across human and rat cannabinoid receptors. In human receptors, it exhibits a Ki of 43.3 +/- 10.3 nM for CB2 and 162.4 +/- 7.6 nM for CB1, functioning as an agonist. However, its interaction with rat receptors reveals a Ki of 16.3 +/- 2.1 nM for CB2 and 1130 +/- 574 nM for CB1, indicating a 6.9-fold lower affinity for rat CB1 receptors than human CB1 receptors. Remarkably, MDA-19 acts as an agonist at human CB1 and CB2 receptors but behaves as an inverse agonist in rat CB2 receptors.

Society and Culture

MDA-19, along with its analogs like MDA-19-Pentyl (5Carbon-MDA-19 / BZO-POXIZID) and 5F-MDA-19 (5F-BZO-POXIZID), has been identified in synthetic smoke blends seized in the United States since September 2021. The United States Border Protection Officers recognized BZO-4en-POXIZID (4en-pentyl-MDA-19) as early as February 2022. The Center for Forensic Science Research & Education (CFSRE) examined 11 suspected synthetic smoke blends between May and September 2022 in the Philadelphia area, discovering the pentyl analog of MDA-19 in 5 out of 11 samples. It’s worth noting that despite their lower CB1 binding affinity, other synthetic cannabinoids like UR-144 and XLR-11 have previously been identified in smoke blends in 2012.

Legality

As of May 22, 2023, MDA-19 is legal at the federal level in the United States. However, it may be considered illegal if intended for human consumption under the federal analog act. In North Dakota, MDA-19, along with several analogs, was placed in Schedule I on April 27, 2023. In China, the ban on specific synthetic cannabinoid core classes in May 2021 does not encompass the class to which MDA-19 belongs.

FAQ

1. What is MDA-19?

  • MDA-19 is a drug known for its selective agonist activity on the cannabinoid receptor CB2, with some variation in its interaction with CB1 receptors, especially between species.

2. How does MDA-19 affect human cannabinoid receptors?

  • In human cannabinoid receptors, MDA-19 binds to CB2 receptors with a Ki of approximately 43.3 +/- 10.3 nM and to CB1 receptors with a Ki of about 162.4 +/- 7.6 nM. It functions as an agonist in human cannabinoid receptors.

3. How does MDA-19 interact with rat cannabinoid receptors?

  • MDA-19 behaves differently with rat cannabinoid receptors, binding to rat CB2 receptors with a Ki of approximately 16.3 +/- 2.1 nM and to rat CB1 receptors with a Ki of around 1130 +/- 574 nM. This indicates significantly weaker binding to rat CB1 receptors, approximately 6.9 times weaker than its interaction with human CB1 receptors. Notably, MDA-19 functions as an inverse agonist in rat CB2 receptors.

4. Is MDA-19 used in the recreational drug culture?

  • MDA-19 and its analogs have been identified in synthetic smoke blends. While they may have some cannabinoid properties, it’s important to note that their use can vary and might not necessarily be for recreational purposes.

5. Is MDA-19 legal for personal use in the United States?

  • As of May 22, 2023, MDA-19 is legal at the federal level in the United States. However, its legality may change depending on its intended use and compliance with federal laws.

6. Is MDA-19 safe for consumption?

  • The safety of MDA-19 for consumption is a matter of concern. It’s essential to remember that substances with potential cannabinoid properties may have various effects and risks, so their use should be approached with caution.

7. What is the legal status of MDA-19 in North Dakota?

  • In North Dakota, MDA-19, along with certain analogs, was placed in Schedule I on April 27, 2023. This means it is legally restricted in the state.

8. How is MDA-19 regulated in China?

  • In China, the class of cannabinoids to which MDA-19 belongs was not included in the ban on specific synthetic cannabinoid core classes in May 2021. However, it’s important to verify the current regulations as they may change over time.

9. Are there any medical applications for MDA-19?

  • While MDA-19 has shown potential interactions with cannabinoid receptors, its primary use has been associated with research, and its medical applications remain largely unexplored.

10. Can MDA-19 cause psychoactive effects?

  • MDA-19 is primarily recognized for its cannabinoid receptor interactions and potential medical properties rather than causing psychoactive effects similar to recreational substances like THC. However, its effects may vary depending on the context and individual reactions.

References

  1. Anvisa’s resolution from July 24, 2023, titled “RDC Nº 804 – Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control” (in Brazilian Portuguese), was officially published in the Diário Oficial da União on July 25, 2023. A copy of this resolution was archived from the original source on August 27, 2023.
  2. The document “Systematic Naming for MDA 19” was made available.
  3. A related document dated August 31, 2021, discusses the “New Systematic Naming for Synthetic Cannabinoid ‘MDA-19’ and its Related Analogues: BZO-HEXOXIZID, 5F-BZO-POXIZID, and BZO-POXIZID.”
  4. Research conducted by Xu JJ, Diaz P, Astruc-Diaz F, Craig S, Munoz E, and Naguib M in July 2010 provides a comprehensive “Pharmacological Characterization of a Novel Cannabinoid Ligand, MDA19,” intended for the treatment of neuropathic pain. This research was published in the journal Anesthesia and Analgesia (Volume 111, Issue 1, pages 99–109, doi:10.1213/ANE.0b013e3181e0cdaf) and is archived under PMC 3253719. The corresponding PMID is 20522703.
  5. In August 2008, Diaz P, Xu J, Astruc-Diaz F, Pan HM, Brown DL, and Naguib M published a paper titled “Design and Synthesis of a Novel Series of N-Alkyl Isatin Acylhydrazone Derivatives that Act as Selective Cannabinoid Receptor 2 Agonists for the Treatment of Neuropathic Pain” in the Journal of Medicinal Chemistry (Volume 51, Issue 16, pages 4932–4947, doi:10.1021/jm8002203). The corresponding PMID is 18666769.
  6. A patent (US 20180200225) assigned to the Cleveland Clinic Foundation, dated July 19, 2018, discusses “Hydrazone modulators of cannabinoid receptors.”
  7. Documents with names like “BZO-CHMOXIZID,” “BZO-POXIZID,” “5F-BZO-POXIZID,” and “BZO-HEXOXIZID” are referenced.
  8. The U.S. Customs and Border Protection Preview reports the identification of two new synthetic cannabinoid analogues.
  9. In September 2022, Krotulski AJ, Shinefeld J, DeBord J, Teixeira da Silva D, and Logan BK published the “Quarterly Drug Checking Report” (PDF) on behalf of the Department of Health, City of Philadelphia. This report is archived and was retrieved on December 16, 2022.
  10. The case of “United States v. Earl Ramos” from the Court of Appeals for the Eighth Circuit, dated February 9, 2016, is referenced.
  11. Techau KW discusses the consequences of synthetic drug sales in a document titled “Synthetic Drug Sales Send a Mother and Her Son to Federal Prison” (PDF) published by the United States Attorney’s Office Northern District of Iowa.
  12. Frost JM, Dart MJ, Tietje KR, Garrison TR, Grayson GK, Daza AV, et al. conducted research in January 2010 on “Indol-3-ylcycloalkyl ketones” and their effects on CB(2) cannabinoid receptor activity. Their findings were published in the Journal of Medicinal Chemistry (Volume 53, Issue 1, pages 295–315, doi:10.1021/jm901214q). The corresponding PMID is 19921781.
  13. Banister SD, Stuart J, Kevin RC, Edington A, Longworth M, Wilkinson SM, et al. examined the effects of bioisosteric fluorine in synthetic cannabinoid designer drugs like JWH-018, AM-2201, UR-144, XLR-11, PB-22, 5F-PB-22, APICA, and STS-135. Their research was published in the ACS Chemical Neuroscience in August 2015 (Volume 6, Issue 8, pages 1445–1458, doi:10.1021/acschemneuro.5b00107). The corresponding PMID is 25921407.
  14. The legal framework related to controlled substance analogues is detailed in “21 U.S. Code § 813.”
  15. On January 3, 2023, an act was passed to amend and reenact sections of the North Dakota Century Code, specifically those related to the scheduling of controlled substances. This act declared an emergency.
  16. The Ministry of Public Security of the People’s Republic of China made an announcement on May 12, 2021, regarding the inclusion of 18 substances, including synthetic cannabinoids and fluamine, in the “Additional Catalogue of Controlled Varieties of Non-medicinal Narcotics and Psychotropic Drugs.”
  17. Details for the country of China are also referenced in the document.

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