U-47700   Click here for help

GtoPdb Ligand ID: 9282

Synonyms: compound 1 [PMID: 2999404]
Compound class: Synthetic organic
Comment: U-47700 is a selective μ-opioid receptor agonist [2], with in vivo effects similar to other potent opioid agonists (analgesia, sedation, euphoria, constipation and respiratory depression). Illicit use and fatalities caused by U-47700 [1,3-4] has prompted action to schedule the compound or make it illegal in some jurisdictions.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 4
Topological polar surface area 23.55
Molecular weight 328.11
XLogP 3.96
No. Lipinski's rules broken 0
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Canonical SMILES CN(C1CCCCC1N(C(=O)c1ccc(c(c1)Cl)Cl)C)C
Isomeric SMILES CN([C@@H]1CCCC[C@H]1N(C(=O)c1ccc(c(c1)Cl)Cl)C)C
InChI 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
1. Armenian P, Olson A, Anaya A, Kurtz A, Ruegner R, Gerona RR. (2017)
Fentanyl and a Novel Synthetic Opioid U-47700 Masquerading as Street "Norco" in Central California: A Case Report.
Ann Emerg Med, 69 (1): 87-90. [PMID:27473610]
2. Cheney BV, Szmuszkovicz J, Lahti RA, Zichi DA. (1985)
Factors affecting binding of trans-N-[2-(methylamino)cyclohexyl]benzamides at the primary morphine receptor.
J Med Chem, 28 (12): 1853-64. [PMID:2999404]
3. Domanski K, Kleinschmidt KC, Schulte JM, Fleming S, Frazee C, Menendez A, Tavakoli K. (2017)
Two cases of intoxication with new synthetic opioid, U-47700.
Clin Toxicol (Phila), 55 (1): 46-50. [PMID:27432224]
4. Elliott SP, Brandt SD, Smith C. (2016)
The first reported fatality associated with the synthetic opioid 3,4-dichloro-N-[2-(dimethylamino)cyclohexyl]-N-methylbenzamide (U-47700) and implications for forensic analysis.
Drug Test Anal, 8 (8): 875-9. [PMID:27232154]