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Abstract
JWH-250 is a synthetic cannabinoid that was named after the researcher John W. Huffman, who discovered it along with a number of other compounds to study the endocannabinoid system of mammals. In May 2009, JWH-250 was first identified by the German Federal Criminal Police as an ingredient in new generation “herbal smoking blends”. Since then, it has gained popularity as a recreational drug due to its psychoactive effects. In May 2009, the German Federal Criminal Police detected JWH-250 in a new generation of “herbal smoking blends”.
This article provides an overview of JWH-250, including its general information, physico-chemical properties, pharmacology in recreational use, and effects and symptoms associated with its use. Additionally, the article covers the street names, prices, and approximate dosage of JWH-250, as well as its legal status and synthesis.
General Information About JWH-250 [1-7]
Other synonyms names of JWH-250 are: 2-(2-Methoxyphenyl)-1-(1-pentyl-1H-indol-3-yl)ethanone; 1-Pentyl-3-(2-methoxyphenylacetyl)indole
IUPAC Name of JWH-250: 2-(2-methoxyphenyl)-1-(1-pentylindol-3-yl)ethanone
CAS number is 864445-43-2
Trade names are J211502; AM-250
Physico-Chemical Properties of JWH-250 [1-7]
- Molecular Formula C22H25NO2
- Molar Weight 335.4 g/mol
- Melting Point 78-80°C
- Solubility: DMF: 25 mg/ml; DMSO: 20 mg/ml; Ethanol: 2 mg/ml; Chloroform
- Color/Form: A crystalline solid; Pale Brown Solid
- Odor: Characteristic
Structural formula present on Figure 1.
Powder and crystalline solid possible of the JWH-250 can be seen in the pictures provided in Figure 2 and Figure 3.
General Information of JWH-250 in Recreational Use and Pharmacology [8, 9]
JWH-250, a synthetic cannabinoid, was developed by John W. Huffman to study the endocannabinoid system of mammals. Its discovery in 2009 as an ingredient in “herbal smoking blends” led to its emergence as a recreational drug. JWH-250 is often consumed as a powder or liquid, and its effects are said to mimic those of marijuana, including feelings of relaxation and euphoria. However, the drug can also cause negative side effects such as anxiety, paranoia, and hallucinations, especially when taken in large amounts. JWH-250 is classified as a Schedule I controlled substance in the United States and is illegal in many other countries as well. Despite its illegality, JWH-250 is still sold on the black market and can be obtained through online sources. Its use as a recreational drug has been associated with a number of adverse health outcomes and even fatalities.
Effects and Symptoms of JWH-250 Use
In vivo studies conducted on mice revealed that JWH-250, upon administration, resulted in significant hypothermia, increased pain threshold to both mechanical and thermal stimuli, induced catalepsy, reduced motor activity, impaired sensorimotor responses to visual, acoustic, and tactile stimuli, caused seizures, myoclonia, hyperreflexia, and triggered aggressive behavior. Additionally, microdialysis studies conducted on freely moving mice showed that JWH-250, when systemically administered, led to dose-dependent stimulation of dopamine release in the nucleus accumbens. The behavioral, neurological, and neurochemical effects of JWH-250 were completely blocked by the selective CB1 receptor antagonist/inverse agonist AM 251. When co-administered with ineffective doses of JWH-073, JWH-250 impaired visual sensorimotor responses, improved mechanical pain threshold, and stimulated mesolimbic dopamine transmission in mice without any changes in other behavioral and physiological parameters. Scientific investigations have demonstrated the overall pharmacological effects of JWH-250 and JWH-073 in mice, indicating their potentially synergistic action, which suggests that the co-administration of different synthetic cannabinoids may increase their harmful effects, thereby escalating their abuse potential. The effects of JWH-250 were compared to those of JWH-018 and Δ9-THC, and their actions were monitored for over 5 hours.
Street Names, Prices and Approximate Dosage
JWH-250 is a synthetic cannabinoid agonist that exhibits nanomolar affinity at CB1 and CB2 receptors. It is commonly marketed illegally in “herbal blends” due to its psychoactive effects that are greater than those produced by cannabis. Recently, an “herbal” preparation containing a mixture of both JWH-250 and JWH-073 was analyzed. These compounds are often mixed in “herbal incense” preparations and sold with attractive packaging under exotic brand names such as “Spice,” “Amazonas,” “Forest Green,” “Jamaican Spirits,” “K2,” and others. The production of these compounds involves a mixture of natural substances such as Piper methysticum, Salvia divinorum, and caffeine, but mostly relies on newly designed and synthesized compounds that have a similar chemical structure to known psychoactive substances. Chemical analyses of different materials have also revealed the presence of a synthetic cannabinoid JWH-250 in 4% of legal highs, which acts as an analgesic.
Common doses taken by people are 2-5 mg when smoking or vaporizing. Labs sell JWH-250 at a price of $23,000 per 10g, while street prices are significantly lower at $630 per 100g and $1900 per 1000g.
Legal Status
JWH-250 is a synthetic cannabinoid that is classified as a Schedule I substance in the United States, making it illegal to possess or distribute. In Australia, it is listed as a Schedule 9 prohibited substance, and in Canada, it is classified as a Schedule II substance. In Germany, it is classified as an Anlage II substance, meaning that it is authorized for trade but not prescriptible. In the United Kingdom, JWH-250 is classified as a Class B drug. The substance is also illegal in the Czech Republic and Latvia. These classifications reflect the potential for abuse and addiction, as well as the potential for harm to individuals who use it.
Synthesis of JWH-250 (AM-250) [10]
JWH-250 is a unique synthetic cannabinoid as it differs from the earlier compounds in the JWH series due to the absence of a naphthalene ring and the presence of a 2′-methoxy-phenylacetyl group instead. The synthesis of JWH-250 and other cannabimimetic indoles involves the use of 1-pentylindole and the appropriate phenylacetyl chloride in a modified Friedel–Crafts reaction called the Okauchi method. This involves stirring the indole substrate in dichloromethane with dimethylaluminum chloride and adding the acyl halide. The process of synthesizing JWH-250 is illustrated in Figure 4.
Conclusion
In recent years, there has been a surge in the use of legal highs or substitute drugs of abuse, including synthetic cannabinoids like JWH-250. These substances are often marketed as a safer alternative to traditional drugs of abuse, but in reality, they can be just as dangerous or even more so. The complex mixtures of active substances in legal highs, including JWH-250, make it difficult to fully understand their impact on the human body. Further research is needed to better understand the potential risks and harms associated with these substances.
Bibliography
- https://en.wikipedia.org/wiki/JWH-250
- https://pubchem.ncbi.nlm.nih.gov/compound/44397540
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- https://www.exportersindia.com/pharma-chem-company5146936/jwh-250-3214524.htm
- Andrea Ossato, Isabella Canazza etc. Effect of JWH-250, JWH-073 and their interaction on “tetrad”, sensorimotor, neurological and neurochemical responses in mice. Progress in Neuro-Psychopharmacology & Biological Psychiatry, 2016, 67, pp. 31–50. https://doi.org/10.1016/j.pnpbp.2016.01.007 https://www.sciencedirect.com/science/article/abs/pii/S0278584616300069?via%3Dihub
- Kinga Mruczyk, Krzysztof Durkalec-Michalski Chemical analysis of substitute drugs of abuse – “legal highs” from Lubuskie province, Poland. Journal of Medical Science, 2014, 2, 83, pp. 101-107. DOI: https://doi.org/10.20883/medical.e52
- John W. Huffman, Paul V. Szklennik 1-Pentyl-3-phenylacetylindoles, a new class of cannabimimetic indoles. Bioorganic & Medicinal Chemistry Letters, 2005, 15, 18, pp. 4110–4113. https://doi.org/10.1016/j.bmcl.2005.06.008 https://www.sciencedirect.com/science/article/abs/pii/S0960894X05007481