General Information About SGT-263 Synthetic Cannabinoid [1]

Other synonyms names of SGT-263 are:

5F-CUMYL-P7AICA; 5-Fluoro cumyl-p7aica; V3J3TQ3UPP; 2171492-36-5; CUMYL-5F-P7AICA;

IUPAC Name of SGT-263:

1-(5-fluoropentyl)-N-(2-phenylpropan-2-yl)pyrrolo[2,3-b]pyridine-3-carboxamide

CAS number is 2171492-36-5

Analogs of SGT-263 are CUMYL‐PINACA, 5F–CUMYL‐PINACA, CUMYL‐4CN‐BINACA and CUMYL‐4CN‐B7AICA

Physico-Chemical Properties of SGT-263 [1]

• Molecular Formula C₂₂H₂₆FN₃O
• Molecular Weight 367.5
• Density 1.1±0.1 g/cm3 [2]
• Boiling Point 588.1±50.0 °C at 760 mmHg [2]
• Flash Point 309.5±30.1 °C [2]
• Index of Refraction 1.574 [2]

Structural formula present on Figure 1.

Powder of SGT-263 present on Figure 2.

General Information of SGT-263 in Recreational Use and Pharmacology [3-10]

Synthetic cannabinoids are a class of novel psychoactive substances that act as agonists at the cannabinoid receptor. One such synthetic cannabinoid is SGT-263, which is known to potentially interact with the CB receptors. These compounds primarily exert their effects via the cannabinoid (CB) receptors, with cannabinoid receptor type 1 (CB1) being primarily responsible for the psychoactive effects. The emergence of 5F-CUMYL‐P7AICA was first documented by the European Monitoring Centre for Drugs and Drug Addiction in 2015, and was subsequently reported to the United Nations Office on Drugs and Crime between 2018 and 2020 [3, 4]. In February 2017, 14 individual packages of eleven “Spice-like” products were analyzed from German language internet shops, identifying three different synthetic cannabinoids, including 5F-Cumyl-P7AICA and Cumyl-PeGACLONE. While these compounds are often difficult to detect in biological matrices such as urine due to their extensive metabolism, the interpretation of toxicological analysis results should be approached with caution as the detection of some metabolites may not necessarily indicate consumption of a specific parent compound. Some biotransformation steps, such as loss of the tail or the linked group, may lead to the formation of metabolites that are identical in different synthetic cannabinoids. Furthermore, smoking may generate pyrolytic artifacts that may not be produced in HLM or human hepatocyte assays [3].

Street Names and Approximate Dosage

New psychoactive compounds known as synthetic cannabinoids are sold as so-called “legal highs,” primarily through internet stores, in the form of herbal smoking mixtures, powders, or e-liquids [5]. Among them, 5F-Cumyl-P7AICA is often present in “Spice-like” products, with a range of 109-153 mg/g and an average of 131 mg/g [6]. While marketed as plant-based incense blends to allegedly serve as room fragrances, these products are well-known for their intended purpose of being smoked like cigarettes to produce cannabis-like effects.

Effects of Cannabinoid Use

Animal testing has revealed that both synthetic cannabinoids and 5F-Cumyl-P7AICA reduce locomotor activity in rats, and higher doses can lead to piloerection, exophthalmos, and convulsions [7]. In one incident, three customs inspectors were exposed to a sticky substance (cumyl-PINACA, an SGT-24 analog of 5F-Cumyl-P7AICA) with their bare fingertips due to package damage and lack of protective gloves. Despite washing their hands with water, signs of synthetic cannabinoid intoxication began to appear half an hour later. By the time they arrived at the Emergency Department six hours later, they were somnolent, lethargic, and confused, displaying symptoms such as mydriasis, blurred vision, ataxia, weakness, numbness, tachycardia, and orthostatic hypotension. Two days later, they reported amnesia and slowed perception of time after exposure, but were feeling better overall. The substance in question was found to be 98% pure, with the intention of being diluted and sold by a drug dealer [8]. See Figure 3 for images of the cumyl-PINACA bottles and structure.

Forms and Appearance of Substances

In their pure form, synthetic cannabinoids are typically powders or oils that can be sprayed onto herbal mixtures and packaged in metal-foil sachets. These herbal mixtures, containing synthetic cannabinoids, are usually smoked, although they are rarely ingested as an infusion. Examples of such herbal mixtures are shown in Figure 4 [9]. SGT-263 is priced at $125 for 10 grams in the form of a faintly yellowish powder.

One reason why Spice may be more potent than marijuana is that the chemical components bind more strongly to the cannabinoid receptor in the brain, and they may also interact with other receptors in the brain that marijuana does not. Symptoms can vary and may resolve spontaneously without intervention, including mild to moderate intoxication-like symptoms, nausea, vomiting, weakness, tachycardia, hypertension, and agitation. However, several news reports have described users in states of “excited delirium,” which involves significant agitation, tearing off clothes, and profuse sweating. Severe symptoms include significant cardiac arrhythmias, myocardial infarction, psychosis, respiratory depression, flaccid paralysis, hyperthermia, rhabdomyolysis, seizures, coma, and even death. Intoxication management typically focuses on airway, breathing, circulation, and life-threatening issues first, followed by supportive care. Fluid resuscitation and electrolyte correction may be necessary. Benzodiazepines are usually the first-line treatment for anxiety/agitation, and physical restraint may be necessary. However, caution should be exercised with antipsychotics and other medications that can lower the seizure threshold, as there have been reports of synthetic cannabinoids causing seizures. Long-term users may be at risk of new-onset or relapse of psychosis and cognitive deficits, including reduced attention span and memory. Withdrawal potential can be unpredictable as well. One case report from Germany describes a daily user of “Spice Gold” over an eight-month period experiencing drug cravings, sweating, hypertension, headache, restlessness, and nightmares. 5F-Cumyl-P7AICA (SGT-263) is believed to be less potent than MMB-Chminaca or SGT-78 and another 13 synthetic cannabinoids. Different cannabinoids are presented in Figure 5.

Synthesis of 1-(5-fluoropentyl)-N-(2-phenylpropan-2-yl)pyrrolo[2,3-b]pyridine-3-carboxamide

Synthesis of 5F-Cumyl-P7AICA starting with 1H-pyrrolo[2, 3-b]pyridine-3-carboxylic acid. Detailed synthesis in [11]. General scheme of SGT-263 synthesis present on Figure 6.

Conclusion

Synthetic cannabinoids and SGT-263 are among the most common types of new psychoactive substances. However, a scientific report detailing the pharmacological properties of these compounds has yet to be published. SGT-263 and its analogues have been shown to undergo extensive metabolism, with some of the metabolic transformations resulting in structurally identical metabolites. Therefore, these metabolites should not be used as a marker for the intake of a specific parent compound. There are cases of fatal outcomes associated with the use of SGT-263, as well as other synthetic cannabinoids. Reports indicate several deaths related to the use of SGT-263 or mixtures containing this cannabinoid. However, it should be noted that there is little official information on lethal outcomes from SGT-263 because this cannabinoid is relatively new and its research is in the early stages.

Bibliography

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