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J-113,397 is an opioid
Condensation between 1-Benzyl-3-methoxycarbonyl-4-piperidone 7611-47-9(1) and O-Phenylenediamine (2) give
CID:16726310
(3). Reaction with boc anhydride followed by treatment with trifluoroacetic acid give
CID:16726358
(4). Reaction with iodoethane in the presence of base alkylates the urea nitrogen givin
CID:16726359
(5). Reduction of the enamine by treatment with magnesium metal in methanol solvent occurs to give predominantly the trans isomer
CID:16726360
(6). Catalytic removal of the benzyl group give
CID:16726362
(7). Reductive amination with Cyclooctanecarbaldehyde 688-11-5(7) give
CID:16726364
(9). Lastly, reduction of the ester with lithium aluminium hydride completed the synthesis of J-113397 (10).
Trap-101
(unsaturated olefin not reduced).
drug
A drug is any chemical substance that causes a change in an organism's physiology or psychology when consumed. Drugs are typically distinguished from food and substances that provide nutritional support. Consumption of drugs can be via insuffla ...
which was the first compound found to be a highly selective antagonist for the nociceptin receptor, also known as the ORL-1 receptor. It is several hundred times selective for the ORL-1 receptor over other opioid receptors, and its effects in animals include preventing the development of tolerance
Tolerance or toleration is the state of tolerating, or putting up with, conditionally.
Economics, business, and politics
* Toleration Party, a historic political party active in Connecticut
* Tolerant Systems, the former name of Veritas Software ...
to morphine, the prevention of hyperalgesia induced by intracerebroventricular administration of nociceptin
Nociceptin/orphanin FQ (N/OFQ), a 17-amino acid neuropeptide, is the endogenous ligand for the nociceptin receptor (NOP, ORL-1). Nociceptin acts as a potent anti-analgesic, effectively counteracting the effect of pain-relievers; it's activation i ...
(orphanin FQ), as well as the stimulation of dopamine
Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic compound, organic chemical of the catecholamine and phenethylamine families. Dopamine const ...
release in the striatum
The striatum, or corpus striatum (also called the striate nucleus), is a nucleus (a cluster of neurons) in the subcortical basal ganglia of the forebrain. The striatum is a critical component of the motor and reward systems; receives glutamate ...
, which increases the rewarding effects of cocaine, but may have clinical application in the treatment of Parkinson's disease.
Synthesis
Patents for treatingarrhythmia
Arrhythmias, also known as cardiac arrhythmias, heart arrhythmias, or dysrhythmias, are irregularities in the heartbeat, including when it is too fast or too slow. A resting heart rate that is too fast – above 100 beats per minute in adults ...
:Guo Zheng, et al. & (2020).
Condensation between 1-Benzyl-3-methoxycarbonyl-4-piperidone 7611-47-9(1) and O-Phenylenediamine (2) giveCID:16726310
(3). Reaction with boc anhydride followed by treatment with trifluoroacetic acid give
CID:16726358
(4). Reaction with iodoethane in the presence of base alkylates the urea nitrogen givin
CID:16726359
(5). Reduction of the enamine by treatment with magnesium metal in methanol solvent occurs to give predominantly the trans isomer
CID:16726360
(6). Catalytic removal of the benzyl group give
CID:16726362
(7). Reductive amination with Cyclooctanecarbaldehyde 688-11-5(7) give
CID:16726364
(9). Lastly, reduction of the ester with lithium aluminium hydride completed the synthesis of J-113397 (10).
See also
*JTC-801
JTC-801 is an opioid analgesic drug used in scientific research.
JTC-801 is a selective antagonist for the nociceptin receptor, also known as the ORL-1 receptor. This was the fourth opioid receptor to be discovered and is still the least unders ...
* LY-2940094
BTRX-246040, also known as LY-2940094, is a potent and selective nociceptin receptor antagonist which is under development by BlackThorn Therapeutics and Eli Lilly for the treatment of major depressive disorder (MDD). It has demonstrated proof ...
* SB-612,111
SB-612,111 is an opioid receptor ligand which is a potent and selective antagonist for the nociceptin receptor (ORL-1), several times more potent than the older drug J-113,397. It does not have analgesic effects in its own right, but prevents th ...
Trap-101
(unsaturated olefin not reduced).
References
{{Opioidergics Synthetic opioids Benzimidazoles Piperidines Ureas Primary alcohols Nociceptin receptor antagonists