CHEBI:75733 - (R,R)-tramadol hydrochloride

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ChEBI Name (R,R)-tramadol hydrochloride
ChEBI ID CHEBI:75733
ChEBI ASCII Name (R,R)-tramadol hydrochloride
Definition A hydrochloride resulting from the reaction of (R,R)-tramadol with 1 molar equivalent of hydrogen chloride; the (R,R)-enantiomer of the racemic opioid analgesic tramadol hydrochloride, it exhibits ten-fold higher analgesic potency than the (S,S)-enantiomer.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C16H26ClNO2
Net Charge 0
Average Mass 299.83600
Monoisotopic Mass 299.16521
InChI InChI=1S/C16H25NO2.ClH/c1-17(2)12-14-7-4-5-10-16(14,18)13-8-6-9-15(11-13)19-3;/h6,8-9,11,14,18H,4-5,7,10,12H2,1-3H3;1H/t14-,16+;/m1./s1
InChIKey PPKXEPBICJTCRU-XMZRARIVSA-N
SMILES Cl.COc1cccc(c1)[C@@]1(O)CCCC[C@@H]1CN(C)C
Roles Classification
Biological Role(s): delta-opioid receptor agonist
A compound that exhibits agonist activity at the delta-opioid receptor.
kappa-opioid receptor agonist
A compound that exhibits agonist activity at the kappa-opioid receptor.
adrenergic uptake inhibitor
Adrenergic uptake inhibitors are drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin.
capsaicin receptor antagonist
Any substance which blocks the painful sensation of heat caused by capsaicin acting on the TRPV1 ion channel.
opioid analgesic
A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
mu-opioid receptor agonist
A compound that exhibits agonist activity at the mu-opioid receptor.
muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
nicotinic antagonist
An antagonist at the nicotinic cholinergic receptor.
NMDA receptor antagonist
Any substance that inhibits the action of N-methyl-D-aspartate (NMDA) receptors. They tend to induce a state known as dissociative anesthesia, marked by catalepsy, amnesia, and analgesia, while side effects can include hallucinations, nightmares, and confusion. Due to their psychotomimetic effects, many NMDA receptor antagonists are used as recreational drugs.
serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
serotonin uptake inhibitor
A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent.
Application(s): delta-opioid receptor agonist
A compound that exhibits agonist activity at the delta-opioid receptor.
kappa-opioid receptor agonist
A compound that exhibits agonist activity at the kappa-opioid receptor.
adrenergic uptake inhibitor
Adrenergic uptake inhibitors are drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin.
antitussive
An agent that suppresses cough. Antitussives have a central or a peripheral action on the cough reflex, or a combination of both. Compare with expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing, and mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration.
opioid analgesic
A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
mu-opioid receptor agonist
A compound that exhibits agonist activity at the mu-opioid receptor.
muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
nicotinic antagonist
An antagonist at the nicotinic cholinergic receptor.
serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
serotonin uptake inhibitor
A compound that specifically inhibits the reuptake of serotonin in the brain. This increases the serotonin concentration in the synaptic cleft which then activates serotonin receptors to a greater extent.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (R,R)-tramadol hydrochloride (CHEBI:75733) has part (R,R)-tramadol(1+) (CHEBI:75737)
(R,R)-tramadol hydrochloride (CHEBI:75733) has role δ-opioid receptor agonist (CHEBI:64054)
(R,R)-tramadol hydrochloride (CHEBI:75733) has role κ-opioid receptor agonist (CHEBI:59282)
(R,R)-tramadol hydrochloride (CHEBI:75733) has role μ-opioid receptor agonist (CHEBI:55322)
(R,R)-tramadol hydrochloride (CHEBI:75733) has role adrenergic uptake inhibitor (CHEBI:35640)
(R,R)-tramadol hydrochloride (CHEBI:75733) has role antitussive (CHEBI:51177)
(R,R)-tramadol hydrochloride (CHEBI:75733) has role capsaicin receptor antagonist (CHEBI:70774)
(R,R)-tramadol hydrochloride (CHEBI:75733) has role muscarinic antagonist (CHEBI:48876)
(R,R)-tramadol hydrochloride (CHEBI:75733) has role nicotinic antagonist (CHEBI:48878)
(R,R)-tramadol hydrochloride (CHEBI:75733) has role NMDA receptor antagonist (CHEBI:60643)
(R,R)-tramadol hydrochloride (CHEBI:75733) has role opioid analgesic (CHEBI:35482)
(R,R)-tramadol hydrochloride (CHEBI:75733) has role serotonergic antagonist (CHEBI:48279)
(R,R)-tramadol hydrochloride (CHEBI:75733) has role serotonin uptake inhibitor (CHEBI:50949)
(R,R)-tramadol hydrochloride (CHEBI:75733) is a hydrochloride (CHEBI:36807)
(R,R)-tramadol hydrochloride (CHEBI:75733) is enantiomer of (S,S)-tramadol hydrochloride (CHEBI:75734)
Incoming tramadol hydrochloride (CHEBI:32250) has part (R,R)-tramadol hydrochloride (CHEBI:75733)
(S,S)-tramadol hydrochloride (CHEBI:75734) is enantiomer of (R,R)-tramadol hydrochloride (CHEBI:75733)
IUPAC Names
(1R,2R)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol hydrochloride
[(1R,2R)-2-hydroxy-2-(3-methoxyphenyl)cyclohexyl]-N,N-dimethylmethanaminium chloride
Synonyms Sources
(+)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol hydrochloride ChEBI
(+)-tramadol hydrochloride ChEBI
Registry Numbers Types Sources
53611-16-8 CAS Registry Number ChemIDplus
6164343 Reaxys Registry Number Reaxys
Last Modified
26 September 2013