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tramadol (CHEBI:9648)

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ChEBI Name tramadol
ChEBI ID CHEBI:9648
Definition A racemate consisting of equal amounts of (R,R)- and (S,S)-tramadol. A centrally acting synthetic opioid analgesic, used (as the hydrochloride salt) to treat moderately severe pain. The (R,R)-enantiomer exhibits ten-fold higher analgesic potency than the (S,S)-enantiomer. Originally developed by Grünenthal GmbH and launched in 1977, it was subsequently isolated from the root bark of the South African tree Nauclea latifolia.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula Source
C16H25NO2 KEGG COMPOUND
Net Charge 0
Average Mass 263.37520
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Biological Role(s): 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.
muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
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.
kappa-opioid receptor agonist
A compound that exhibits agonist activity at the kappa-opioid receptor.
delta-opioid receptor agonist
A compound that exhibits agonist activity at the delta-opioid receptor.
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.
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.
nicotinic antagonist
An antagonist at the nicotinic cholinergic receptor.
capsaicin receptor antagonist
Any substance which blocks the painful sensation of heat caused by capsaicin acting on the TRPV1 ion channel.
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
Application(s): 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.
muscarinic antagonist
A drug that binds to but does not activate muscarinic cholinergic receptors, thereby blocking the actions of endogenous acetylcholine or exogenous agonists.
opioid analgesic
A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
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.
mu-opioid receptor agonist
A compound that exhibits agonist activity at the mu-opioid receptor.
kappa-opioid receptor agonist
A compound that exhibits agonist activity at the kappa-opioid receptor.
delta-opioid receptor agonist
A compound that exhibits agonist activity at the delta-opioid receptor.
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.
serotonergic antagonist
Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or serotonergic agonists.
nicotinic antagonist
An antagonist at the nicotinic cholinergic receptor.
View more on the ChEBI Ontology
ChEBI Ontology
Outgoing tramadol (CHEBI:9648) has part (R,R)-tramadol (CHEBI:75725)
tramadol (CHEBI:9648) has part (S,S)-tramadol (CHEBI:75731)
tramadol (CHEBI:9648) has role δ-opioid receptor agonist (CHEBI:64054)
tramadol (CHEBI:9648) has role κ-opioid receptor agonist (CHEBI:59282)
tramadol (CHEBI:9648) has role μ-opioid receptor agonist (CHEBI:55322)
tramadol (CHEBI:9648) has role adrenergic uptake inhibitor (CHEBI:35640)
tramadol (CHEBI:9648) has role antitussive (CHEBI:51177)
tramadol (CHEBI:9648) has role capsaicin receptor antagonist (CHEBI:70774)
tramadol (CHEBI:9648) has role environmental contaminant (CHEBI:78298)
tramadol (CHEBI:9648) has role muscarinic antagonist (CHEBI:48876)
tramadol (CHEBI:9648) has role nicotinic antagonist (CHEBI:48878)
tramadol (CHEBI:9648) has role NMDA receptor antagonist (CHEBI:60643)
tramadol (CHEBI:9648) has role opioid analgesic (CHEBI:35482)
tramadol (CHEBI:9648) has role serotonergic antagonist (CHEBI:48279)
tramadol (CHEBI:9648) has role serotonin uptake inhibitor (CHEBI:50949)
tramadol (CHEBI:9648) has role xenobiotic (CHEBI:35703)
tramadol (CHEBI:9648) is a racemate (CHEBI:60911)
tramadol (CHEBI:9648) is conjugate base of tramadol(1+) (CHEBI:75736)
Incoming tramadol(1+) (CHEBI:75736) is conjugate acid of tramadol (CHEBI:9648)
IUPAC Name
rac-(1R,2R)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol
INNs Sources
tramadol WHO MedNet
tramadol WHO MedNet
tramadol WHO MedNet
tramadolum DrugBank
Synonyms Sources
(±)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol ChEBI
CG-315E ChEBI
E-265 ChEBI
U-26225A ChEBI
Database Links Databases
C07153 KEGG COMPOUND
D08623 KEGG DRUG
DB00193 DrugBank
GB997399 Patent
HMDB14339 HMDB
Tramadol Wikipedia
US3652589 Patent
View more database links
Registry Numbers Types Sources
27203-92-5 CAS Registry Number KEGG COMPOUND
27203-92-5 CAS Registry Number ChemIDplus
2943832 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
18 November 2014

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