ADB-PINACA

ADB-PINACA
Legal status
Legal status	CA: Schedule II; DE: NpSG (Industrial and scientific use only); UK: Class B; US: Schedule I;
Identifiers
	IUPAC name N-(1-Amino-3,3-dimethyl-1-oxo-2-butanyl)-1-pentyl-1H-indazole-3-carboxamide;
CAS Number	1633766-73-0 ;
PubChem CID	86280478;
ChemSpider	29342129;
UNII	U1Q4F41C9U;
CompTox Dashboard (EPA)	DTXSID301010007 ;
Chemical and physical data
Formula	C19H28N4O2
Molar mass	344.459 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCN1C2=CC=CC=C2C(=N1)C(=O)NC(C(=O)N)C(C)(C)C;
	InChI InChI=1S/C19H28N4O2/c1-5-6-9-12-23-14-11-8-7-10-13(14)15(22-23)18(25)21-16(17(20)24)19(2,3)4/h7-8,10-11,16H,5-6,9,12H2,1-4H3,(H2,20,24)(H,21,25); Key:FWTARAXQGJRQKN-UHFFFAOYSA-N;

ADB-PINACA is a cannabinoid designer drug that is an ingredient in some synthetic cannabis products. It is a potent agonist of the CB₁ receptor and CB₂ receptor with EC₅₀ values of 0.52 nM and 0.88 nM respectively.^[1]^[2] Like MDMB-FUBINACA, this compound incorporates the unnatural amino acid tert-leucine.

Side effects

ADB-PINACA has been linked to multiple hospitalizations and deaths due to its use.^[3]^[4]^[5]

Metabolism

Nineteen ADB-PINACA major metabolites were identified in several incubations with cryopreserved human hepatocytes. Major metabolic reactions included pentyl hydroxylation, hydroxylation followed by oxidation (ketone formation), and glucuronidation.^[6]

Legality

ADB-PINACA is listed in the Fifth Schedule of the Misuse of Drugs Act (MDA) and therefore illegal in Singapore as of May 2015.^[7]

In the United States, it is a Schedule I controlled substance.^[8] but its 5'-bromo analog ADB-5'Br-PINACA is not as of October 20th, 2023.

As of October 2015 ADB-PINACA is a controlled substance in China.^[9]

References

^ Banister SD, Moir M, Stuart J, Kevin RC, Wood KE, Longworth M, et al. (September 2015). "Pharmacology of Indole and Indazole Synthetic Cannabinoid Designer Drugs AB-FUBINACA, ADB-FUBINACA, AB-PINACA, ADB-PINACA, 5F-AB-PINACA, 5F-ADB-PINACA, ADBICA, and 5F-ADBICA". ACS Chemical Neuroscience. 6 (9): 1546–59. doi:10.1021/acschemneuro.5b00112. PMID 26134475.
^ "ADB-PINACA". Forendex. Archived from the original on 2014-07-14. Retrieved 2014-07-09.
^ "CDC: 221 sickened by synthetic pot in Colorado". USA Today. December 12, 2013.
^ Schwartz MD, Trecki J, Edison LA, Steck AR, Arnold JK, Gerona RR (May 2015). "A Common Source Outbreak of Severe Delirium Associated with Exposure to the Novel Synthetic Cannabinoid ADB-PINACA". The Journal of Emergency Medicine. 48 (5): 573–80. doi:10.1016/j.jemermed.2014.12.038. PMC 9049074. PMID 25726258.
^ Trecki J, Gerona RR, Schwartz MD (July 2015). "Synthetic Cannabinoid-Related Illnesses and Deaths". The New England Journal of Medicine. 373 (2): 103–7. doi:10.1056/NEJMp1505328. PMID 26154784.
^ Carlier J, Diao X, Scheidweiler KB, Huestis MA (May 2017). "Distinguishing Intake of New Synthetic Cannabinoids ADB-PINACA and 5F-ADB-PINACA with Human Hepatocyte Metabolites and High-Resolution Mass Spectrometry". Clinical Chemistry. 63 (5): 1008–1021. doi:10.1373/clinchem.2016.267575. PMID 28302730.
^ "CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. Archived from the original on 15 July 2015. Retrieved 24 July 2015.
^ Drug Enforcement Administration, Department of Justice (February 2014). "Schedules of controlled substances: temporary placement of four synthetic cannabinoids into Schedule I. Final order". Federal Register. 79 (27): 7577–82. PMID 24605391.
^ "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). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.

[1] Banister SD, Moir M, Stuart J, Kevin RC, Wood KE, Longworth M, et al. (September 2015). "Pharmacology of Indole and Indazole Synthetic Cannabinoid Designer Drugs AB-FUBINACA, ADB-FUBINACA, AB-PINACA, ADB-PINACA, 5F-AB-PINACA, 5F-ADB-PINACA, ADBICA, and 5F-ADBICA". ACS Chemical Neuroscience. 6 (9): 1546–59. doi:10.1021/acschemneuro.5b00112. PMID 26134475.

[2] "ADB-PINACA". Forendex. Archived from the original on 2014-07-14. Retrieved 2014-07-09.

[3] "CDC: 221 sickened by synthetic pot in Colorado". USA Today. December 12, 2013.

[4] Schwartz MD, Trecki J, Edison LA, Steck AR, Arnold JK, Gerona RR (May 2015). "A Common Source Outbreak of Severe Delirium Associated with Exposure to the Novel Synthetic Cannabinoid ADB-PINACA". The Journal of Emergency Medicine. 48 (5): 573–80. doi:10.1016/j.jemermed.2014.12.038. PMC 9049074. PMID 25726258.

[5] Trecki J, Gerona RR, Schwartz MD (July 2015). "Synthetic Cannabinoid-Related Illnesses and Deaths". The New England Journal of Medicine. 373 (2): 103–7. doi:10.1056/NEJMp1505328. PMID 26154784.

[6] Carlier J, Diao X, Scheidweiler KB, Huestis MA (May 2017). "Distinguishing Intake of New Synthetic Cannabinoids ADB-PINACA and 5F-ADB-PINACA with Human Hepatocyte Metabolites and High-Resolution Mass Spectrometry". Clinical Chemistry. 63 (5): 1008–1021. doi:10.1373/clinchem.2016.267575. PMID 28302730.

[7] "CNB NEWS RELEASE". Central Narcotics Bureau (CNB). 30 April 2015. Archived from the original on 15 July 2015. Retrieved 24 July 2015.

[pmid24605391-8] Drug Enforcement Administration, Department of Justice (February 2014). "Schedules of controlled substances: temporary placement of four synthetic cannabinoids into Schedule I. Final order". Federal Register. 79 (27): 7577–82. PMID 24605391.

[9] "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). China Food and Drug Administration. 27 September 2015. Archived from the original on 1 October 2015. Retrieved 1 October 2015.

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Side effects

Metabolism

Legality

See also

References