Abstract

ADB-PINACA is a synthetic cannabinoid of the indazole-3-carboxamide class that has recently been found in various herbal mixtures. Its mechanism of action involves full agonism at both CB1 and CB2 cannabinoid receptors, resulting in more severe clinical effects than those produced by marijuana. Although commercial products containing synthetic cannabinoids are sold as “herbal incense” and labeled “not for human consumption,” they are often consumed for their psychoactive effects.

This article provides a comprehensive overview of ADB-PINACA, including general information about the substance, its physico-chemical properties, and its pharmacology in recreational use. It also covers topics such as detoxification, the effects and symptoms associated with ADB-PINACA use, common street names, pricing, and approximate dosages. Additionally, the legal status of ADB-PINACA is discussed, as well as the synthesis of the substance.

The Hard Lives of Britain’s Synthetic Marijuana Addicts

General Information About ADB-PINACA [1-5]

Other synonyms names of ADB-PINACA are: N-[1-(aminocarbonyl)-2,2-dimethylpropyl]-1-pentyl-1h-indazole-3-carboxamide; N-(1-Carbamoyl-2,2-dimethylpropyl)-1-pentyl-1H-indazole-3-carboxamide

IUPAC Name of ADB-PINACA: N-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-1-pentylindazole-3-carboxamide

CAS number is 1633766-73-0

Physico-Chemical Properties of ADB-PINACA [1-5]

• Molecular Formula C₁₉H₂₈N₄O₂
• Molar Weight 344.5 g/mol
• Boiling point 590.5±30.0 °C at 760 mmHg
• Flash Point: 310.9±24.6 °C

Structural formula present on Figure 1.

Powder and crystalline solid possible of the ADB-PINACA can be seen in the picture provided in Figure 2.

General Information of ADB-PINACA in Recreational Use and Pharmacology [6-12]

ADB-PINACA is a synthetic cannabinoid of the indazole-3-carboxamide class that has been recently discovered in various herbal blends. Its pharmacological activity involves acting as a full agonist at both CB1 and CB2 cannabinoid receptors, with an EC50 of 0.59 nM and 0.88 nM, respectively. ADB-PINACA also contains a L-tert-leucinamide side chain.

When ADB-PINACA binds to CB receptors, it results in Gi/o-mediated inhibition of adenylate cyclase, leading to a decrease in intracellular cAMP concentration. Studies using experimental mice models have shown that ADB-PINACA usage results in a decrease in locomotor activity similar to that of Δ9-THC, but with a much faster onset of manifestations compared to other synthetic cannabinoid receptor agonists.

While ADB-PINACA is often marketed as a “legal high” and sold as an “herbal blend” or “potpourri,” its use poses significant health risks to users. The substance has been associated with acute toxicity, severe side effects, and even death in some cases. As such, ADB-PINACA and other synthetic cannabinoids should be avoided. More research is needed to fully understand the effects and potential dangers of ADB-PINACA and similar substances.

Detoxication

Currently, there is no specific antidote available for synthetic cannabinoid (SC) intoxication. However, certain treatments may help manage the symptoms associated with SC use. For instance, midazolam, lorazepam, or diazepam may be administered through IV with larger doses given through intramuscular injection if IV access is unavailable. Benzodiazepines are often used to control agitation and psychosis associated with SC intoxication, and occasionally, an antipsychotic agent like haloperidol may be used when benzodiazepines fail to have an effect.

Intravenous fluids may also be administered to correct acidosis and hyperglycemia. In addition, potassium supplements may be needed to correct hypokalemia. If the patient experiences tachycardia or chest pain, an electrocardiogram (ECG) is recommended. For individuals who develop seizures, nonspecific sedative-hypnotic agents such as benzodiazepines, barbiturates, and propofol may be used. However, specific antiepileptic medications like phenytoin or levetiracetam may not be effective in treating drug-induced seizures.

After acute SC intoxication, mental status typically improves within a few hours, but it may take up to 24 hours for the symptoms to subside entirely. It is important to note that the use of SC and other novel psychoactive substances can pose severe health risks, and immediate medical attention should be sought in the case of overdose or adverse reactions. More research is needed to better understand the long-term effects of SC use and to develop more effective treatments for SC intoxication.

Effects and Symptoms of ADB-PINACA Use

The use of ADB-PINACA, a potent synthetic cannabinoid, has been associated with hospitalizations and fatalities. It is often used as an alternative to marijuana, with users seeking a more intense psychoactive experience while evading detection in drug screenings. ADB-PINACA and other synthetic cannabinoids have been found to be more potent than delta-9-tetrahydrocannabinol, the active ingredient in marijuana. The use of synthetic cannabinoids has been linked to seizures, chest pain, and cardiovascular toxicity. ADB-PINACA undergoes similar metabolic transformations, with its N-pentanoic acid metabolite detectable in serum or plasma samples for much longer than the parent compound. The clinical effects of ADB-PINACA are severe, including agitated delirium, lethargy, coma, seizures, tachycardia, hypertension, and hallucinations. Treatment primarily focuses on airway protection and controlling agitation and seizures. In 2013, 263 possible cases of ADB-PINACA toxicity were reported, with 76 patients presenting to local hospitals in Colorado. Synthetic cannabinoids have also been linked to acute kidney injury, stroke, coma, and death.

EFFECTS of synthetic marijuana

Street Names, Prices and Approximate Dosage

Common street names for ADB-PINACA include “Crazy Clown”, ‘‘Black Mamba’’, and “10X”. ADB-PINACA was first discovered in the SC-containing product ‘‘Crazy Clown’’ which was seized by law enforcement and identified as the smoked product.

Synthetic cannabinoids, also known as SCs, are commonly used as an alternative to marijuana. They are usually dissolved in a solvent and applied to dried plant material or herbal potpourri before being smoked, vaped, or consumed in other ways. Some of the street names for SCs include “Spice”, “K2”, and “Black Mamba”. The SC-containing products are often marketed as “herbal incense” and labeled “not for human consumption” to avoid legal restrictions.

One of the synthetic cannabinoids that has been identified in SC-containing products is ADB-PINACA, which was found in samples of a product called Crazy Clown seized by law enforcement. ADB-PINACA is a novel pentyl indazole SC and is sold commercially for laboratory use at a price of 105€ per 1 mg or 309€ per 5 mg. However, on the street, the prices are much lower, with 100 grams of SCs selling for around $630 and 1000 grams selling for around $2300. Despite their lower price, the use of SCs can be dangerous and can cause a variety of health problems.

Legal Status

ADB-PINACA is a highly regulated substance across the world. In the state of Georgia, it is categorized as a Schedule I substance, while in Singapore, it is listed in the Fifth Schedule of the Misuse of Drugs Act (MDA) and has been illegal since May 2015. The United States also classifies ADB-PINACA as a Schedule I controlled substance, and it was added to the DEA Schedule I classification. As of October 2015, China also listed ADB-PINACA as a controlled substance. These strict regulations reflect the potential dangers associated with the use of ADB-PINACA, including severe toxicity and even death.

Synthesis of ADB-PINACA [6, 13]

A complete synthesis of ADB-PINACA is described in detail in reference [6 and 13]. Figure 3 outlines the synthetic scheme for the production of ADB-PINACA.

What goes on inside a Chinese ‘legal high’ factory? BBC News

Conclusion

ADB-PINACA is a synthetic cannabinoid belonging to the indazole-3-carboxamide class and has been found in herbal mixtures. It acts as a potent full agonist at both CB1 and CB2 cannabinoid receptors, and its street names include “Crazy Clown”, “Black Mamba”, and “10X”. There is currently no known specific antidote for synthetic cannabinoid intoxication, which is typically achieved through smoking or vaping. The DEA has classified ADB-PINACA as a Schedule I substance.

Bibliography

1. https://en.wikipedia.org/wiki/ADB-PINACA
2. https://pubchem.ncbi.nlm.nih.gov/compound/86280478
3. https://www.chemspider.com/Chemical-Structure.29342129.html
4. https://www.biosynth.com/p/CA175142/1633766-73-0-adb-pinaca
5. https://www.caymanchem.com/product/ISO00150/adb-pinaca
6. Banister et al. 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 Chem. Neurosci., 2015, 6, 9, pp. 1546–1559. https://doi.org/10.1021/acschemneuro.5b00112 https://pubs.acs.org/doi/abs/10.1021/acschemneuro.5b00112
7. Michael B. Gatch, Michael J. Forster ∆9-Tetrahydrocannabinol-like effects of novel synthetic cannabinoids in mice and rats. Psychopharmacology, 2016, 233, 10, pp. 1901-1910. https://doi.org/10.1007/s00213-016-4237-6 https://link.springer.com/article/10.1007/s00213-016-4237-6
8. Schoeder, C.T., Hess, C., Madea, B. et al. Pharmacological evaluation of new constituents of “Spice”: synthetic cannabinoids based on indole, indazole, benzimidazole and carbazole scaffolds. Forensic Toxicol, 2018, 36, pp. 385–403. https://doi.org/10.1007/s11419-018-0415-z https://link.springer.com/article/10.1007/s11419-018-0415-z
9. Jordan Trecki, Roy R. Gerona Synthetic Cannabinoid–Related Illnesses and Deaths. N. Engl. J. Med., 2015, 373, pp. 103-107. DOI: 10.1056/NEJMp1505328 https://www.nejm.org/doi/10.1056/NEJMp1505328
10. Michael D. Schwartz, Jordan Trecki A common source outbreak of severe delirium associated with exposure to the novel synthetic cannabinoid adb-pinaca. The Journal of Emergency Medicine, 2015, Vol. 48, Issue 5, pp. 573-580. DOI:https://doi.org/10.1016/j.jemermed.2014.12.038 https://www.jem-journal.com/article/S0736-4679(14)01425-5/fulltext
11. Patil Armenian, Michael Darracq etc. Intoxication from the novel synthetic cannabinoids AB-PINACA and ADB-PINACA: A case series and review of the literature. Neuropharmacology, 2018, Volume 134, Part A, pp. 82-91. https://doi.org/10.1016/j.neuropharm.2017.10.017 https://www.sciencedirect.com/science/article/abs/pii/S0028390817304835
12. https://www.dea.gov/factsheets/spice-k2-synthetic-marijuana
13. http://bbzzzsvqcrqtki6umym6itiixfhni37ybtt7mkbjyxn2pgllzxf2qgyd.onion/threads/synthesis-of-adb-pinaca.330/