AM-2201 (1-(5-fluoropentyl)-3-(1-naphthoyl)indole) is a

recreational Recreation is an activity of leisure, leisure being discretionary time. The "need to do something for recreation" is an essential element of human biology and psychology. Recreational activities are often done for enjoyment, amusement, or pleasur ...

designer drug A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. Des ...

that acts as a potent but nonselective

full agonist An agonist is a chemical that activates a receptor to produce a biological response. Receptors are cellular proteins whose activation causes the cell to modify what it is currently doing. In contrast, an antagonist blocks the action of the ago ...

for the

cannabinoid receptor Cannabinoid receptors, located throughout the body, are part of the endocannabinoid system a class of cell membrane receptors in the G protein-coupled receptor superfamily. As is typical of G protein-coupled receptors, the cannabinoid recepto ...

. It is part of the AM series of cannabinoids discovered by

Alexandros Makriyannis Alexandros Makriyannis (born September 9, 1939) is an American biochemist and professor of Chemistry and Chemical Biology in the Department of Medicinal Chemistry at Northeastern University in Boston, Massachusetts, where he directs the Center for ...

Northeastern University Northeastern University (NU) is a private university, private research university with its main campus in Boston. Established in 1898, the university offers undergraduate and graduate programs on its main campus as well as satellite campuses in ...

Hazards

Convulsions A convulsion is a medical condition where the body muscles contract and relax rapidly and repeatedly, resulting in uncontrolled shaking. Because epileptic seizures typically include convulsions, the term ''convulsion'' is sometimes used as a s ...

have been reported including at doses as low as 10 mg.

Pharmacology

AM-2201 is a

for

s. Affinities are: with a ''K''_i of 1.0 nM at CB₁ and 2.6 nM at CB₂. The 4-methyl functional analog

MAM-2201 MAM-2201 (4'-methyl-AM-2201, 5"-fluoro-JWH-122) is a drug that presumably acts as a potent agonist for the cannabinoid receptors. It had never previously been reported in the scientific or patent literature, and was first identified by laborato ...

probably has similar affinities. AM-2201 has an EC₅₀ of 38 nM for human CB₁ receptors, and 58 nM for human CB₂ receptors. AM-2201 produces

bradycardia Bradycardia (also sinus bradycardia) is a slow resting heart rate, commonly under 60 beats per minute (BPM) as determined by an electrocardiogram. It is considered to be a normal heart rate during sleep, in young and healthy or elderly adults, a ...

and hypothermia in rats at doses of 0.3–3 mg/kg, comparable to the potency of

JWH-018 JWH-018 (1-pentyl-3-(1-naphthoyl)indole, NA-PIMO or AM-678) is an analgesic chemical from the naphthoylindole family that acts as a full agonist at both the CB1 and CB2 cannabinoid receptors, with some selectivity for CB2. It produces effects in ...

in rats, suggesting potent cannabinoid-like activity.

Pharmacokinetics

AM-2201

metabolism Metabolism (, from el, μεταβολή ''metabolē'', "change") is the set of life-sustaining chemical reactions in organisms. The three main functions of metabolism are: the conversion of the energy in food to energy available to run cell ...

differs only slightly from that of

. AM-2201 ''N''-

dealkylation Alkylation is the transfer of an alkyl group from one molecule to another. The alkyl group may be transferred as an alkyl carbocation, a free radical, a carbanion, or a carbene (or their equivalents). Alkylating agents are reagents for effecting al ...

produces fluoropentane instead of pentane (or plain

alkane In organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which ...

s in general).

Detection

A forensic standard of AM-2201 is available, and the compound has been posted on the Forendex website of potential drugs of abuse.

Legal status

In the United States, AM-2201 is a

Schedule I controlled substance This is the list of Schedule I drugs as defined by the United States Controlled Substances Act. 21 CFRbr>1308.11(CSA Sched I) with changes through (Oct 18, 2012). Retrieved September 6, 2013. The following findings are required for drugs to be pl ...

.Controlled Substances listed by the DEA
/ref>

References

{{Cannabinoidergics Naphthoylindoles Organofluorides AM cannabinoids Designer drugs CB1 receptor agonists CB2 receptor agonists