Abstract

Synthetic cannabinoids (SCs) are a relatively new class of psychoactive drugs that are commonly used for recreational purposes. However, their usage comes with potential health risks, which have been closely monitored by the EU Early Warning System since 2010 due to the severe adverse effects they can have on consumers. JWH-210 is a type of naphthoylindole synthetic cannabinoid that acts as a potent agonist at both the CB1 and CB2 receptors. This makes it one of the most potent 4-substituted naphthol derivatives within the naphthoylindole family, binding to the CB1 receptor with greater affinity than other compounds within the JWH series.

This article aims to provide a comprehensive overview of JWH-210, including general information about the drug, its physico-chemical properties, pharmacology in recreational use, its effects and symptoms, street names, approximate prices and dosages, legal status, synthesis methods of JWH-210, conclusion, and bibliography.

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General Information About JWH-210 [1-3]

Other synonyms names of JWH-210 are: 1-Pentyl-3-(4-ethyl-1-napthoyl)indole; (4-ethylnaphthalen-1-yl)(1-pentyl-1H-indol-3-yl)methanone;

IUPAC Name of JWH-210: (4-ethylnaphthalen-1-yl)-(1-pentylindol-3-yl)methanone

CAS numbers are 824959-81-1; 824960-02-3

Trade names are legal highs, herbal incense, K2, Spice; Maya; Bonzai; Blaze; Push

Physico-Chemical Properties of JWH-210 [1-3]

• Molecular Formula C₂₆H₂₇NO
• Molar Weight 369.5 g/mol
• Boiling point 558.7±33.0 °C at 760 mmHg
• Melting Point 90.2 °C
• Flash Point: 291.7±25.4 °C
• Solubility: DMF: 50 mg/ml; DMSO: 20 mg/ml; Ethanol: 0.5 mg/ml
• Color/Form: Solid; Pink powder
• Odor: Characteristic

Structural formula present on Figure 1.

Powder and Spices possible of the JWH-210 can be seen in the pictures provided in Figure 2 and Figure 3.

General Information of JWH-210 in Recreational Use and Pharmacology [4-7]

JWH-210 is a lab-made cannabinoid that is utilized in the United States for analyzing wastewater samples to detect synthetic cannabinoids. This compound can be identified at concentrations as low as 10 parts per billion (ppb). JWH-210 has been detected in various bodily fluids, such as urine samples and cell culture supernatants, as well as wastewater. The use of high performance liquid chromatography (HPLC) with ultraviolet detection (UV) is an effective method for detecting JWH-210. JWH-210 has a strong affinity for cannabinoid CB1 receptors, with a binding affinity that is 90 times higher than that of THC. It also has a 50 times higher affinity for CB2 receptors than THC. Recently, there has been an increase in the recreational use of highly potent synthetic cannabinoids like JWH-210. There have been several documented cases of driving under the influence (DUI) and both nonfatal and fatal incidents associated with the recreational use of JWH-210.

Effects and symptoms of JWH-210 Use

A study on JWH-210 found that at a dosage of 2 mg, some participants reported experiencing hypotension, headache, dizziness, vomiting, and self-limited mild stabbing chest pain. Despite exhibiting THC-like effects on heart rate, blood pressure, and subjective experience, JWH-210 showed these effects with lower intensity. No significant toxic effects were found at the low dose administered. However, some participants experienced tachycardia, nausea, somnolence, hypokalemia, hypertension, restlessness, and/or agitation. Other reported symptoms included diplopia, seizures, syncope, and changes in electrocardiogram readings such as T-wave inversion and bradycardia. Acute adverse effects of JWH-210 commonly involved central nervous system depression or cerebral seizures, as well as signs of sympathomimetic toxicity. Nausea was reported in 80% of cases and typically had a sudden onset shortly after inhalation, suggesting a possible central nervous system effect mediated by CB1 receptors. Cardiovascular effects were also reported in up to 80% of patients, including changes in blood pressure, heart rate, and electrocardiogram readings. Most symptoms resolved within 4-18 hours, with a median of 8 hours. The most frequently reported effects were tachycardia, nausea, somnolence, mydriasis, mild hypokalemia, skin pallor, hypertension, restlessness/agitation, disorientation, and visual hallucinations. Overdoses of JWH-210 commonly resulted in central nervous system depression, with agitation and cerebral seizures also occurring in some cases. These findings suggest that JWH-210 acts as a potent CB1 receptor agonist, confirming previous reports of adverse effects after inhalation of synthetic cannabinoids. However, the clinical pattern of overdose is distinct compared to other cannabinoids.

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Street Names, Prices and Approximate Dosage

JWH-210 is a synthetic cannabinoid that is known to be sold under various street names such as K2, Spice, Maya, Bonzai, Blaze, and Push. It is primarily used as a recreational drug due to its psychoactive effects. However, it is important to note that the drug can pose significant health risks if used in excessive amounts.

The cost of JWH-210 can vary depending on its intended use. For laboratory purposes, the drug is sold at around 515€ per 25 mg. However, on the streets, the drug can be purchased for as much as 630$ per 100g, or 1900$ per 1000g. The wide discrepancy in cost between laboratory and street prices is a clear indication of the drug’s illicit nature and the potential for abuse.

To minimize the risks associated with JWH-210 use, it is recommended that users consume doses ranging from 2-3 mg only. The dosage was established by Energy Control, an organization that promotes drug safety and harm reduction. This recommendation takes into account the drug’s potential adverse effects on the central nervous system, such as tachycardia, nausea, and seizures. It is important for users to take caution when consuming JWH-210, especially in uncontrolled environments where the drug’s purity and concentration cannot be guaranteed.

Legal Status

JWH-210, along with other CB1 receptor agonists, is classified as a Schedule I Controlled Substance in the United States. This means that it is illegal to manufacture, distribute, or possess without proper authorization. In Sweden, JWH-210 was banned in 2010 after being identified as an ingredient in “herbal” synthetic cannabis products. Subsequently, it, along with JWH-122 and JWH-203, was classified as an illegal drug by the Swedish government. As of 2015, JWH-210 is also a controlled substance in China. In Canada, it is classified as a Schedule II drug, meaning it is legal for medical use but only available with a prescription. In the UK, JWH-210 is a Class B drug, meaning it is illegal to possess, produce, or supply. It is also illegal in Poland where it is classified as I-N. It is important to note that JWH-210 is a highly potent and potentially dangerous substance that should not be used without proper medical supervision. In Germany – Anlage II (Authorized trade only, not prescriptible).

Synthesis of JWH-210 [6, 7]

Starting from the scheme shown in Figure 4, JWH-210 can be synthesized through a multi-step process. The synthesis of JWH-210 involves the reaction of 4-ethyl-2-naphthoyl chloride with 1-pentyl-1H-indole under heat, followed by dissolving the resulting substance in ethanol or another solvent and crystallizing it. 4-Ethyl-2-naphthoyl chloride prepared from
corresponding carboxylic acid using thionyl chloride.

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Conclusion

JWH-210 is a synthetic cannabinoid that has shown to be a potent agonist at the CB1 and CB2 receptors. Its high binding affinity to the CB1 receptor makes it one of the most potent naphthoylindole derivatives in the JWH series. In fact, JWH-210 has a binding affinity at CB1 receptors that is 90 times higher than that of THC, and a CB2 receptor affinity that is 50 times higher than THC.

Although it has similar effects to THC, JWH-210 can cause adverse effects at lower doses than THC. Overdoses of JWH-210 commonly result in central nervous system depression, with agitation and cerebral seizures occurring in some cases. Due to these health risks, JWH-210 and other synthetic cannabinoids have been classified as illegal drugs in many countries.

It is important to note that synthetic cannabinoids like JWH-210 have not been well studied in humans and their long-term effects are unknown. Therefore, individuals should avoid using these substances as they may cause serious harm to their health.

Bibliography

1. https://en.wikipedia.org/wiki/JWH-210
2. https://pubchem.ncbi.nlm.nih.gov/compound/45270396
3. https://www.chemspider.com/Chemical-Structure.24617616.html
4. Lucia Martínez, Nunzia La Maida Acute Pharmacological Effects and Oral Fluid Concentrations of the Synthetic Cannabinoids JWH-122 and JWH-210 in Humans After Self-Administration: An Observational Study. Front. Pharmacol., 2021, Sec. Neuropharmacology, Volume 12 – 2021. https://doi.org/10.3389/fphar.2021.705643 https://www.frontiersin.org/articles/10.3389/fphar.2021.705643/full
5. Maren Hermanns-Clausen, Josephine Kithinji Adverse effects after the use of JWH-210 – a case series from the EU Spice II plus project. Drug Test. Analysis, 2016, Volume 8, Issue 10, pp. 1030-1038. https://doi.org/10.1002/dta.1936 https://analyticalsciencejournals.onlinelibrary.wiley.com/doi/10.1002/dta.1936
6. Lindsey Hess, Uma Sreenivasan, Kenan Yaser Regioselective Friedel-Crafts Type Acylation of Indoles: An Improvement on the Synthesis of Cannabimimetic Indole Metabolites. American Chemical Society (ACS), Dallas, TX, March 16-20, 2014. https://www.cerilliant.com/newsAndEvents/posterArticle.aspx?ID=64
7. Giovanni Appendino, Alberto Minassia, Orazio Taglialatela-Scafati Recreational drug discovery: natural products as lead structures for the synthesis of smart drugs. Nat. Prod. Rep., 2014, 31, pp. 880-904. DOI: 10.1039/c4np00010b https://pubs.rsc.org/en/content/articlelanding/2014/NP/c4np00010b