U-47700

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U-47700
U-47700 molecule.svg
Systematic (IUPAC) name
trans-3,4-dichloro-N-(2-(dimethylamino)cyclohexyl)-N-methylbenzamide
Clinical data
Legal status
  • Illegal in Finland, Sweden, Ohio
Identifiers
CAS Number 121348-98-9
PubChem CID: 13544015
ChemSpider 23113403 YesY
ChEMBL CHEMBL2311130
Chemical data
Formula C16H22Cl2N2O
Molecular mass 329.27 g·mol−1
  • ClC1=C(C=CC(=C1)C(=O)N(C)[C@@H]2CCCC[C@H]2N(C)C)Cl
  • InChI=1S/C16H22Cl2N2O/c1-19(2)14-6-4-5-7-15(14)20(3)16(21)11-8-9-12(17)13(18)10-11/h8-10,14-15H,4-7H2,1-3H3/t14-,15-/m1/s1
  • Key:JGPNMZWFVRQNGU-HUUCEWRRSA-N
 NYesY (what is this?)  (verify)

U-47700[1] is an opioid analgesic drug developed by a team at Upjohn in the 1970s.[2] U-47700 was derived from an earlier opioid AH-7921. U-47700 is selective for the µ-opioid receptor with a Kd value of 5.3 nM compared to 910 nM for the κ-opioid receptor[3][4] and has around 7.5 x the potency of morphine in animal models.[5][6]

U-47700 is the result of a great deal of work elucidating the quantitative structure–activity relationship of the scaffold. The team looked for the key moieties which gave the greatest activity.[7] Upjohn posted over a dozen patents on related compounds, each optimizing one moiety[8][9][10][11][12][13][14] until they discovered that U-47700 was the most active.[15]

U-47700 became the lead compound of selective kappa-opioid receptor ligands such as U-50488 (containing a single methylene spacer difference) and U-69,593, which share very similar structures.[3] Its structure led to other chemists experimenting with it to see if rigid analogues would retain activity.[16] Although not used medically, the selective kappa ligands are used in research.[17]

Side effects

U-47700 has never been studied in 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.[18] Tolerance and dependence would be expected to develop.[original research?]

Combined consumption of U-47700 and fentanyl caused one fatality in Belgium.[19][20] At least 17 opioid overdoses and several deaths in the USA have been connected with the use of U-47700.[21]

Legal status

Following its sale as a designer drug, U-47700 was made illegal in Sweden on 26 January 2016.[22]

U-47700 was emergency scheduled in Ohio on 3 May 2016.[23]

See also

References

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  23. ↑ Lua error in package.lua at line 80: module 'strict' not found.


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