NNE1 (also known as NNEI, MN-24 and AM-6527) is an

indole Indole is an aromatic heterocyclic organic compound with the formula C8 H7 N. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered pyrrole ring. Indole is widely distributed in the natural environme ...

-based

synthetic cannabinoid Synthetic cannabinoids are a class of designer drug molecules that bind to the same receptors to which cannabinoids ( THC, CBD and many others) in cannabis plants attach. These novel psychoactive substances should not be confused with synth ...

, representing a

molecular hybrid A molecule is a group of two or more atoms held together by attractive forces known as chemical bonds; depending on context, the term may or may not include ions which satisfy this criterion. In quantum physics, organic chemistry, and bioche ...

of APICA and

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 a ...

that is an

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 recep ...

s, with ''K''_i values of 60.09 nM at CB₁ and 45.298 nM at CB₂ and EC₅₀ values of 9.481 nM at CB₁ and 1.008 nM at CB₂. It was invented by

Abbott Abbott may refer to: People *Abbott (surname) *Abbott Handerson Thayer (1849–1921), American painter and naturalist * Abbott and Costello, famous American vaudeville act Places Argentina * Abbott, Buenos Aires United States * Abbott, Arkansas ...

and has a CB₁ receptor pEC₅₀ of 8.9 with around 80x selectivity over the related CB₂ receptor. It is suspected that metabolic hydrolysis of the amide group of NNE1 may release

1-naphthylamine 1-Naphthylamine is an aromatic amine derived from naphthalene. It can cause bladder cancer (transitional cell carcinoma). It crystallizes in colorless needles which melt at 50 °C. It possesses a disagreeable odor, sublimes readily, and turn ...

, a known

carcinogen A carcinogen is any substance, radionuclide, or radiation that promotes carcinogenesis (the formation of cancer). This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes. Several radioactive subst ...

, given the known metabolic liberation (and presence as an impurity) of

amantadine Amantadine, sold under the brand name Gocovri among others, is a medication used to treat dyskinesia associated with parkinsonism and influenza caused by type A influenzavirus, though its use for the latter is no longer recommended due to wi ...

in the related compound

APINACA APINACA (AKB48, ''N''-(1-adamantyl)-1-pentyl-1''H''-indazole-3-carboxamide) is a drug that acts as a reasonably potent agonist for the cannabinoid receptors, with a Ki of 304.5nM and an EC50 of 585nM at CB1. It had never previously been report ...

, and NNE1 was banned in New Zealand in 2012 as a

temporary class drug A temporary class drug is a relatively new status for controlled drugs, which has been adopted in some jurisdictions, notably New Zealand and the United Kingdom, to attempt to bring newly synthesised designer drugs under legal control. The controll ...

to stop it being used as an ingredient in then-legal

synthetic cannabis Synthetic cannabinoids are a class of designer drug molecules that bind to the same receptors to which cannabinoids ( THC, CBD and many others) in cannabis plants attach. These novel psychoactive substances should not be confused with syntheti ...

products. NNE1 was subsequently found to be responsible for the death of a man in Japan in 2014.

References

Designer drugs Naphthoylindoles Indolecarboxamides {{cannabinoid-stub

See also

References