MDA-19

MDA-19 was first synthesized and studied in the late 2000s by researchers at the University of Texas MD Anderson Cancer Center.{{cite patent |country= US |number= 20180200225 |status= |title= Hydrazone modulators of cannabinoid receptors|pubdate= 19 July 2018 |gdate= |fdate= |pridate= |inventor= Attala MN, Diaz P |assign1= Cleveland Clinic Foundation |url= https://patents.google.com/patent/US20180200225A1/en }}{{cite web |title=BZO-CHMOXIZID |url=https://www.npsdiscovery.org/wp-content/uploads/2021/11/BZO-CHMOXIZID_111821_CFSRE-Chemistry_Report.pdf }}

MDA-19 binds to human CB₂ receptors at K_i = 43.3 ± 10.3 nM and human CB₁ receptors at K_i = 162.4 ± 7.6 nM and functions as an agonist in human cannabinoid receptors but functions differently in rat cannabinoid receptors binding to rat cannabinoid CB₂ receptors at K_i = 16.3 ± 2.1 and CB₁ receptors at K_i = 1130 ± 574 nM binding to rat CB₁ receptors 6.9× weaker than human CB₁ receptors but increased binding for CB₂. MDA-19 is an agonist at human CB₁ and CB₂ receptors as well as rat CB₁ receptors but functions as an inverse agonist in rat CB₂ receptors.

MDA-19 along with its shortened Pentyl tailchain analog (MDA-19-Pentyl / 5Carbon-MDA-19/ BZO-POXIZID){{cite web |title=BZO-POXIZID |url=https://www.npsdiscovery.org/wp-content/uploads/2021/10/BZO-POXIZID_101921_CFSRE-Chemistry_Report.pdf }} and its 5-Fluoro Pentyl analog (5F-MDA-19 /5F-BZO-POXIZID){{cite web |title=5F-BZO-POXIZID |url=https://www.npsdiscovery.org/wp-content/uploads/2021/10/5F-BZO-POXIZID_101921_CFSRE-Chemistry_Report.pdf }} and its Cyclohexylmethyl analog (CHM-MDA-19 / BZO-CHMOXIZID) was identified in synthetic smoke blends seized in the United States as early as September 2021.{{cite web |title=BZO-HEXOXIZID |url=https://www.npsdiscovery.org/wp-content/uploads/2021/10/BZO-HEXOXIZID_101921_CFSRE-Chemistry_Report.pdf }} United States Border Protection Officers identified BZO-4en-POXIZID (also known as 4en-pentyl-MDA-19) as early as February, 2022{{cite web | url=https://www.cbp.gov/newsroom/local-media-release/cbp-officers-and-scientists-identify-two-new-synthetic-cannabinoid | title=CBP Officers and Scientists Identify Two New Synthetic Cannabinoid Analogues | U.S. Customs and Border Protection Preview }} The Center for Forensic Science Research & Education (CFSRE) analyzed 11 samples of suspected synthetic smoke blends between May and September 2022 within the Philadelphia area and found the pentyl analog of MDA-19 in 5 out of 11 samples.{{cite web | vauthors = Krotulski AJ, Shinefeld J, DeBord J, Teixeira da Silva D, Logan BK | date = September 2022 | publisher = Department of Health, City of Philadelphia |title= Quarterly Drug Checking Report |url= https://www.cfsre.org/images/content/reports/drug_checking/2022_Q3_Drug_Checking_Quarterly_Report_Philadelphia.pdf |pages=2 |archive-url=https://web.archive.org/web/20221216050742/https://www.cfsre.org/images/content/reports/drug_checking/2022_Q3_Drug_Checking_Quarterly_Report_Philadelphia.pdf |archive-date=2022-12-16 }} Despite their reported lower CB₁ binding affinity, other low CB₁ binding synthetic cannabinoids such as UR-144 (K_i = 150 nM CB₁ and K_i = 1.8 nM CB₂) and XLR-11 (EC₅₀ values of 98 nM CB₁ and 83 nM CB₂) have been previously identified in smoke blends in 2012.{{cite court |litigants= United States v. Earl Ramos |vol= |reporter= |opinion= |pinpoint= |court= Court of Appeals for the Eighth Circuit |date= 9 February 2016 |url= https://www.courtlistener.com/opinion/3175788/united-states-v-earl-ramos/ |access-date= |quote= |postscript= }}{{cite web | vauthors = Techau KW | title = Synthetic Drug Sales Send a Mother and Her Son to Federal Prison| url = http://cdn.radioiowa.com/wp-content/uploads/2015/03/Ramos-sentencing-PDF.pdf | work = United States Attorney’s Office Northern District of Iowa }}{{cite journal | vauthors = Frost JM, Dart MJ, Tietje KR, Garrison TR, Grayson GK, Daza AV, El-Kouhen OF, Yao BB, Hsieh GC, Pai M, Zhu CZ, Chandran P, Meyer MD | display-authors = 6 | title = Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity | journal = Journal of Medicinal Chemistry | volume = 53 | issue = 1 | pages = 295–315 | date = January 2010 | pmid = 19921781 | doi = 10.1021/jm901214q }}{{cite journal | vauthors = Banister SD, Stuart J, Kevin RC, Edington A, Longworth M, Wilkinson SM, Beinat C, Buchanan AS, Hibbs DE, Glass M, Connor M, McGregor IS, Kassiou M | display-authors = 6 | title = Effects of Bioisosteric Fluorine in Synthetic Cannabinoid Designer Drugs JWH-018, AM-2201, UR-144, XLR-11, PB-22, 5F-PB-22, APICA, and STS-135 | journal = ACS Chemical Neuroscience | volume = 6 | issue = 8 | pages = 1445–1458 | date = August 2015 | pmid = 25921407 | doi = 10.1021/acschemneuro.5b00107 | url = https://zenodo.org/record/47750 }}

In the United States, As of October 20, 2024 MDA-19 is legal at the federal level, but may be considered illegal if intended for human consumption under the federal analogue act.{{Cite web|url=https://www.law.cornell.edu/uscode/text/21/813|title = 21 U.S. Code § 813 - Treatment of controlled substance analogues}}

North Dakota has placed MDA-19 (along with BZO-CHMOXIZID (CHM-MDA-19), BZO-POXIZID (Pentyl MDA-19), 5F-BZO-POXIZID (5F-MDA-19) and BZO-4en-POXIZID (4en-pentyl MDA-19) into Schedule I on 04/27/23.{{cite web | title = AN ACT to amend and reenact sections 19-03.1-05, 19-03.1-11, and 19-03.1-13 of the North Dakota Century Code, relating to the scheduling of controlled substances; and to declare an emergency. | url = https://www.ndlegis.gov/prod/assembly/68-2023/regular/documents/23-8099-04000.pdf | work = Sixty-eighth Legislative Assembly of North Dakota in Regular Session | date = 3 January 2023 }}

In China, the May 2021 ban on specific synthetic cannabinoid core classes does not include the class of cannabinoids MDA-19 belongs to.{{cite web | date = 12 May 2021 | title = 关于将合成大麻素类物质和氟胺酮等18种物质列入《非药用类麻醉药品和精神药品管制品种增补目录》的公告 | trans-title = Announcement on the inclusion of 18 substances including synthetic cannabinoids and fluamine in the "Additional Catalogue of Controlled Varieties of Non-medicinal Narcotics and Psychotropic Drugs" | language = Chinese | url = https://app.mps.gov.cn/gdnps/pc/content.jsp?id=7881703 | work = Ministry of Public Security of the People's Republic of China }}{{Cite web |url= https://www.unodc.org/LSS/Country/Details/CN |title = Details for Country CHINA }}

• BZO-CHMOXIZID
• JWH-007
• JWH-116
• JWH-196
• AM-1221
• JWH-015
• JWH-047
• JWH-167
• JTE 7-31
• UR-144
• XLR-11

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{{Cannabinoids}}

Category:Cannabinoids