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 environmen ...
-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 synthetic ...
, representing a
molecular hybrid of
APICA APICA or Apica may refer to:
Toponyms
* Apica River, stream in Charlevoix Regional County Municipality, Capitale-Nationale, Quebec, Canada
* Mont-Apica, Quebec, unorganized territory in Lac-Saint-Jean-Est Regional County Municipality, Saguenayâ ...
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 recepto ...
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 CB
1 and 1.008 nM at CB
2. It was invented by
Abbott and has a
CB1 receptor pEC
50 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 substan ...
, 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 wid ...
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 control ...
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 synthetic ...
products. NNE1 was subsequently found to be responsible for the death of a man in Japan in 2014.
See also
*
5F-NNE1
*
5F-PCN
*
AM-2201
AM-2201 (1-(5-fluoropentyl)-3-(1-naphthoyl)indole) is a recreational designer drug that acts as a potent but nonselective full agonist for the cannabinoid receptor. It is part of the AM series of cannabinoids discovered by Alexandros Makriyanni ...
*
APICA APICA or Apica may refer to:
Toponyms
* Apica River, stream in Charlevoix Regional County Municipality, Capitale-Nationale, Quebec, Canada
* Mont-Apica, Quebec, unorganized territory in Lac-Saint-Jean-Est Regional County Municipality, Saguenayâ ...
*
CUMYL-PICA
CUMYL-PICA (SGT-56) is an indole-3-carboxamide based synthetic cannabinoid. It is the α,α-dimethylbenzyl analogue of SDB-006. It was briefly sold in New Zealand during 2013 as an ingredient of at the time legal synthetic cannabis products, but ...
*
FDU-NNE1
FDU-NNE1 (also known as FDU-NNEI and FDU-MN-24) is an indole-based synthetic cannabinoid that is presumed to be a potent agonist of the CB1 receptor and has been sold online as a designer drug. Given the known metabolic liberation (and presence ...
*
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 ...
*
NM-2201
NM-2201 (also known as CBL-2201) is an indole-based synthetic cannabinoid that presumably has similar properties to the closely related 5F-PB-22 and NNE1, which are both full agonists and unselectively bind to CB1 and CB2 receptors with low n ...
*
SDB-005
SDB-005 is an indazole-based synthetic cannabinoid that has been sold online as a designer drug. It is presumed to be an agonist of the CB1 and CB2 cannabinoid receptors. SDB-005 is the indazole core analog of PB-22 where the 8-hydroxyquinoline ...
References
Designer drugs
Naphthoylindoles
Indolecarboxamides
{{cannabinoid-stub