U-47700

 

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CAS Number: 82657-23-6
Formula:C16H22Cl2N2O
Molar mass:329.27 g·mol−1
PubChem CID: 13544016
ChemSpider:23113403
UNII:6IY4WX208T
ChEMBL:CHEMBL277572
IUPAC name: 3,4-Dichloro-N-[(1R,2R)-2-(dimethylamino)cyclohexyl]-N-methylbenzamide

U-47700 is an opioid analgesic drug developed by a team at Upjohn in the 1970s that acts as a selective agonist of the µ-opioid receptor with a Kd value of 5.3 nM compared to 910 nM for the κ-opioid receptorand has around 7.5 x the potency of morphine in animal models.

U-47700 is a structural isomer of the earlier opioid AH-7921[7] and the result of a great deal of work elucidating the quantitative structure–activity relationship of the scaffold. Upjohn looked for the key moieties which gave the greatest activity and posted over a dozen patents on related compounds, each optimizing one moiety until they discovered that U-47700 was the most active.

U-47700 became the lead compound of selective kappa-opioid receptor ligands such as U-50488, U-51754 (containing a single methylene spacer difference) and U-69,593, which share very similar structures.Although not used medically, the selective kappa ligands are used in research.

U-47700 has never been studied on humans, but would be expected to produce effects similar to those of other potent opioid agonists, including strong analgesia, sedation, euphoria, constipation, itching and respiratory depression which could be harmful or fatal. Tolerance and dependence would be expected to develop.

Combined consumption of U-47700 and fentanyl caused one fatality in Belgium.17 opioid overdoses and several deaths in the USA had initially been associated with U-47700 in April 2016, as of September 2016 at least 15 fatalities were confirmed.

Following its sale as a designer drug, U-47700 was made illegal in Sweden on 26 January 2016.

U-47700 was emergency scheduled in Ohio on 3 May 2016 by executive order of Governor John Kasich.

U-47700 was emergency scheduled in Florida on 27 September 2016 by an emergency rule of Florida Attorney General Pam Bondi.

Responding to the imminent threat to public health and safety, the U.S. Drug Enforcement Administration has placed U-47700 into Schedule 1 of the Controlled Substances Act, effective November 14, 2016.