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EG-2201

eg-2201EG-2201 goes by the formal and systematic IUPAC name (9-(5-fluoropentyl)-9H-carbazol-3-yl)(naphthalen-1-yl)methanone, has a molecular formula C28H24FNO and a relative molar mass of 409.5 grams. It forms a neat solid at room temperature and pressure.

The synthetic cannabinoid EG2201 is an analogue of the more well known AM2201. AM 2201 is known to be a potent synthetic cannabinoid with a binding affinity of 1 nM for the human cannabinoid receptor CB1 and 2.6 nM for the human cannabinoid receptor CB2.

EG-2201 deviates in structure from AM2201 in that it has a benzene ring fused to the aminoalkylindole moiety.

EG-2201 belongs to the class of synthetic cannabinoids known as aminoalkylindoles. These molecules were first synthesised by the now redundant pharmaceutical corporation Sterling-Winthorp as potential drug leads for a new non-steroidal anti-inflammatory medicinal agent. However these chemicals are currently known in forensic science as one class of synthetic cannabinoids within the increasingly complex ecosystem of synthetic cannabinoids used for their propensity to produce a “high” when ingested.

As of 2013 the aminoalkylindole class was the most prevalent cannabinoid. Popular members of this group included JWH-200, JWH-072 and JWH-018. The JWH series of aminoalkylindole class of cannabinoids were synthesised by Clemson professor J.W Huffmann. They may be synthesised in a simple two step process – so easy in fact that many of the original analogues were first synthesised by undergraduate summer research students within his laboratory.

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AM2201 largely emerged in following the 2011 ban of JWH-018. AM2201 was in fact many degrees more potent than JWH-018. Thus as an unforeseen consequence of legislation a molecule was banned and in its place vendors began selling a more potent analogue. It was the substitution on the pentyl side chain of a fluoride molecule that introduced a significant increase in binding affinity to CB1. This is part of a trend of fluorination of synthetic cannabinoids in recent years which has lead to increasing potency and potential toxicity.

EG2201 then with its fusion of a benzene ring to the structure of AM2201 can be seen as part of a lineage of aminoalkylindole cannabinoids from JWH-018. EG2201 is also fluorinated at the pentyl side chain which should impart it the typically high binding affinity to CB1 and CB2.

This full agonist action and extremely high binding affinity at CB1 is in contrast to the partial agonist action of THC, the primary psychoactive constituent of the herbal drug marijuana, at CB1. Cannabinoids like THC and others from marijuana do not contain nitrogen or indeed highly electrophilic atoms such as fluorine. The synthetic cannabinoids that do contain nitrogen and importantly fluorine then bind much more strongly to CB1 producing a profile of effects that far exceed those of traditional cannabis in strength and duration. Synthetic cannabinoids also come with a risk of hospitalisation, seizure, overdose and death.

EG-2201 is untested in humans and not fit for consumption by humans or animals.

Subjective and unverifiable online reports claim that this chemical produces a highly sedative and potent marijuana type high in very small doses. Synthetic cannabinoids should be ingested by a cold method. It is speculated that heat may produce toxic combustion products owing to the presence of fluorine and nitrogen in the molecule. Online reports also state that doses are extremely small and measured using milligram scales and volumetric titration methods. There are some reports of overdosage and dependency.