CHEBI:75725 - (R,R)-tramadol

ChEBI IDCHEBI:75725
ChEBI Name(R,R)-tramadol
Stars
ASCII Name(R,R)-tramadol
DefinitionA 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol in which both stereocentres have R-configuration; the (R,R)-enantiomer of the racemic opioid analgesic tramadol, it exhibits ten-fold higher analgesic potency than the (S,S)-enantiomer.
Last Modified25 February 2016
SubmitterSteve
DownloadsMolfile
FormulaC16H25NO2
Net Charge0
Average Mass263.381
Monoisotopic Mass263.18853
SMILESCOc1cccc([C@@]2(O)CCCC[C@@H]2CN(C)C)c1
InChIInChI=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
InChIKeyTVYLLZQTGLZFBW-ZBFHGGJFSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
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.
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.
kappa-opioid receptor agonist  A compound that exhibits agonist activity at the κ-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.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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 μ-opioid 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.
delta-opioid receptor agonist  A compound that exhibits agonist activity at the δ-opioid receptor.
serotonergic antagonist  Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
Applications:
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.
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.
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.
kappa-opioid receptor agonist  A compound that exhibits agonist activity at the κ-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.
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 μ-opioid receptor.
delta-opioid receptor agonist  A compound that exhibits agonist activity at the δ-opioid receptor.
serotonergic antagonist  Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
ChEBI Ontology
Outgoing Relation(s)
(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) 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) 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 Relation(s)
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  Source
(+)-tramadolChEBI
(+)-trans-2-(Dimethylaminomethyl)-1-(m-methoxyphenyl)cyclohexanolChemIDplus
Manual XrefsDatabases
3008VSDB
C07153KEGG COMPOUND
D08623KEGG DRUG
LSM-5221LINCS
TramadolWikipedia
Registry NumbersSources
Reaxys:9590387Reaxys
CAS:123154-38-1ChemIDplus
CAS:27203-92-5KEGG COMPOUND