Compound: Tapentadol
SMILES: Oc1cc(ccc1)[C@@H]([C@H](CN(C)C)C)CC
InChIKey: KWTWDQCKEHXFFR-SMDDNHRTSA-N
Synonyms: Tapentadol, 175591-23-8, CG5503, BN 200 (BASE), CG5503 (BASE), BN 200, BN-200, CG-5503, CG5503 IR, 3-((1R,2R)-3-(Dimethylamino)-1-ethyl-2-methylpropyl)phenol, H8A007M585, NSC-759619, CG 5503, DTXSID30170003, phenol, 3-[(1r,2r)-3-(dimethylamino)-1-ethyl-2-methylpropyl]-, Phenol, 3-((1R,2R)-3-(dimethylamino)-1-ethyl-2-methylpropyl)-, 3-[(1r,2r)-3-(dimethylamino)-1-ethyl-2-methylpropyl]phenol, 3-((2R,3R)-1-dimethylamino-2-methylpentan-3-yl)phenol, 3-[(2R,3R)-1-dimethylamino-2-methylpentan-3-yl]phenol, tapentadolum, RefChem:58438, DTXCID1092494, Tapentadol [USAN:INN], 3-[(2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl]phenol, 3-((2R,3R)-1-(dimethylamino)-2-methylpentan-3-yl)phenol, DEA No. 9780, UNII-H8A007M585, HSDB 8309, Tapentadol [INN], (R,R)-Tapentadol, TAPENTADOL [MI], Tapentadol (USAN/INN), TAPENTADOL [USAN], TAPENTADOL [VANDF], TAPENTADOL [MART.], TAPENTADOL [WHO-DD], SCHEMBL116924, GTPL7477, CHEMBL1201776, SCHEMBL29447436, SCHEMBL29611116, CHEBI:135935, KWTWDQCKEHXFFR-SMDDNHRTSA-N, CS-M0020, BDBM50386381, AKOS015951190, DB06204, NSC 759619, NS00002711, D06007, Q414463, BRD-K04283354-003-01-9, (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methyl-propyl)-phenol
Theoretical properties:
molecular_formula: C14H23NO
molecular_weight: 221.34 g/mol
exact_mass: 221.177964357 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 5
heavy_atom_count: 16
topological_polar_surface_area: 23.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
melting_point: 202-205
Descriptions:
{"pubchem": "Tapentadol is an alkylbenzene.", "chebi": null, "chembl": "TAPENTADOL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Tapentadol, sold under the brand names Nucynta and Palexia among others, is a synthetic opioid analgesic with a dual mode of action as a highly selective full agonist of the \u03bc-opioid receptor and as a norepinephrine reuptake inhibitor (NRI). Tapentadol is used medically for the treatment of moderate to severe pain. It is highly addictive and is a commonly abused drug.  \nFrequently reported adverse effects include euphoria, constipation, nausea, vomiting, headaches, loss of appetite, drowsiness, dizziness, itching, dry mouth, and sweating.  More severe adverse reactions can occur, including addiction and dependence, substance abuse, respiratory depression, and an elevated risk of serotonin syndrome. Concurrent use of tapentadol with serotonergic drugs or central nervous system depressants \u2013 including alcohol, cannabis, benzodiazepines, and other opioids \u2013 can heighten the risks of excessive serotonin accumulation, profound sedation, dangerously slowed breathing and death. \nAnalgesia occurs within 32 minutes of oral administration, and lasts for 4\u20136 hours. Tapentadol is taken by mouth, and is available in immediate-release and controlled-release formulations. Tapentadol's combined mechanism of action is often compared to that of tramadol. Unlike tramadol, tapentadol is not metabolised by cytochrome P450 enzymes, but rather through glucuronidation. Due to this, tapentadol has fewer interactions with other medications and fewer side effects when compared with tramadol.  \nLike tramadol, tapentadol affects both the opioid system and the norepinephrine system to relieve pain. Unlike tramadol, it has only weak effects on the reuptake of serotonin and is a significantly more potent opioid with no known active metabolites. The potency of tapentadol is somewhere between that of tramadol and morphine, with an analgesic efficacy comparable to that of oxycodone despite a lower incidence of side effects. The CDC Opioid Guidelines Calculator estimates a conversation rate of 50mg of tapentadol equaling 10 mg of oral oxycodone in terms of opioid receptor activation. \nIn the late 1980s, Gr\u00fcnenthal developed tapentadol to improve on tramadol, which they had created in 1962. Their goal was to design a molecule that minimized serotonin activity, strongly activated the \u03bc-opioid receptor, inhibited norepinephrine reuptake, and worked without metabolic activation. The result was tapentadol. Due to the high risk of addiction, substance misuse, and dependence, tapentadol is a Schedule II controlled substance in the United States, a Schedule 8 controlled drug in Australia, and a Class A controlled substance in the United Kingdom."}