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(R,R)-tramadol (CHEBI:75725)

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ChEBI Name (R,R)-tramadol
ChEBI ID CHEBI:75725
ChEBI ASCII Name (R,R)-tramadol
Definition A 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol in which both stereocentres have R-configuation; the (R,R)-enantiomer of the racemic opioid analgesic tramadol, it exhibits ten-fold higher analgesic potency than the (S,S)-enantiomer.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula Source
C16H25NO2 ChEBI
Net Charge 0
Average Mass 263.37520
InChI
InChI=1S/C16H25NO2/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/t14-,16+/m1/s1
InChIKey
TVYLLZQTGLZFBW-ZBFHGGJFSA-N
SMILES
COc1cccc(c1)[C@@]1(O)CCCC[C@@H]1CN(C)C
Roles Classification
Biological Role(s): serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
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.
mu-opioid receptor agonist
A compound that exhibits agonist activity at the mu-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.
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.
opioid analgesic
A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
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.
metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
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.
mu-opioid receptor agonist
A compound that exhibits agonist activity at the mu-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.
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.
opioid analgesic
A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
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 on the ChEBI Ontology
ChEBI Ontology
Outgoing (R,R)-tramadol (CHEBI:75725) has role δ-opioid receptor agonist (CHEBI:64054)
(R,R)-tramadol (CHEBI:75725) has role κ-opioid receptor agonist (CHEBI:59282)
(R,R)-tramadol (CHEBI:75725) has role μ-opioid receptor agonist (CHEBI:55322)
(R,R)-tramadol (CHEBI:75725) has role adrenergic uptake inhibitor (CHEBI:35640)
(R,R)-tramadol (CHEBI:75725) has role antitussive (CHEBI:51177)
(R,R)-tramadol (CHEBI:75725) has role capsaicin receptor antagonist (CHEBI:70774)
(R,R)-tramadol (CHEBI:75725) has role metabolite (CHEBI:25212)
(R,R)-tramadol (CHEBI:75725) has role muscarinic antagonist (CHEBI:48876)
(R,R)-tramadol (CHEBI:75725) has role nicotinic antagonist (CHEBI:48878)
(R,R)-tramadol (CHEBI:75725) has role NMDA receptor antagonist (CHEBI:60643)
(R,R)-tramadol (CHEBI:75725) has role opioid analgesic (CHEBI:35482)
(R,R)-tramadol (CHEBI:75725) has role serotonergic antagonist (CHEBI:48279)
(R,R)-tramadol (CHEBI:75725) has role serotonin uptake inhibitor (CHEBI:50949)
(R,R)-tramadol (CHEBI:75725) is a 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol (CHEBI:75722)
(R,R)-tramadol (CHEBI:75725) is conjugate base of (R,R)-tramadol(1+) (CHEBI:75737)
(R,R)-tramadol (CHEBI:75725) is enantiomer of (S,S)-tramadol (CHEBI:75731)
Incoming tramadol (CHEBI:9648) has part (R,R)-tramadol (CHEBI:75725)
(R,R)-tramadol(1+) (CHEBI:75737) is conjugate acid of (R,R)-tramadol (CHEBI:75725)
(S,S)-tramadol (CHEBI:75731) is enantiomer of (R,R)-tramadol (CHEBI:75725)
IUPAC Name
(1R,2R)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol
Synonyms Sources
(+)-tramadol ChEBI
(+)-trans-2-(Dimethylaminomethyl)-1-(m-methoxyphenyl)cyclohexanol ChemIDplus
Database Links Databases
C07153 KEGG COMPOUND
D08623 KEGG DRUG
Tramadol Wikipedia
View more database links
Registry Numbers Types Sources
123154-38-1 CAS Registry Number ChemIDplus
27203-92-5 CAS Registry Number KEGG COMPOUND
9590387 Reaxys Registry Number Reaxys
Last Modified
28 July 2014

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