File:Tramadol_as_a_racemic_mixture.svg · Wikimedia Commons · See Wikimedia Commons
tramadol
Sign in to saveAlso known as (+)-trans-2-(dimethylaminomethyl)-1-(m-methoxyphenyl)cyclohexanol, (+)-tramadol, 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol, (R,R)-tramadol
Tramadol, sold under the brand name Tramal among others, is an opioid pain medication and a serotonin–norepinephrine reuptake inhibitor (SNRI) used to treat moderate to severe pain. When taken by mouth in an immediate-release formulation, the onset of pain relief usually begins within an hour. It is also available by injection. It is available in combination with paracetamol (acetaminophen).
Key facts
- Drug.PubChem
- 33741
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 451973921
- Drug.image
- Tramadol as a racemic mixture.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 250
- Drug.width2
- 200
- Drug.imageL
- (1S,2S)-Tramadol molecule ball.png
- Drug.image_classL
- bg-transparent
- Drug.imageR
- (1R,2R)-Tramadol molecule spacefill.png
- Drug.image_classR
- bg-transparent
- Drug.pronounce
- /ˈtræməˌdɒl/
- Drug.tradename
- Tramal, others
- Drug.MedlinePlus
- a695011
- Drug.DailyMedID
- Tramadol
- Drug.pregnancy_AU
- C
- Drug.dependency_liability
- Yes, misuse and dependence reported
via Wikipedia infobox
Chemical data
- Formula
- C16H25NO2
- Molecular weight
- 263.37 g/mol
- IUPAC name
- cis-(1R,2R)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol
- SMILES
- CN(C)C[C@H]1CCCC[C@@]1(C2=CC(=CC=C2)OC)O
- InChIKey
- TVYLLZQTGLZFBW-ZBFHGGJFSA-N
- XLogP
- 2.6
- Polar surface area
- 32.7 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Research
8,015 papersvia PubMed
Wikidata facts
- Mass
- 263.188529
Show 5 more facts
- chemical formula
- C₁₆H₂₅NO₂
- Commons category
- Tramadol
- isomeric SMILES
- CN(C)C[C@H]1CCCC[C@@]1(C2=CC(=CC=C2)OC)O
- canonical SMILES
- CN(C)CC1CCCCC1(C2=CC(=CC=C2)OC)O
- stylized name
- traMADol
Sources (3)
via Wikidata · CC0
~33 min read
Article
33 sectionsContents
- Medical uses
- Pain relief
- Off-label uses
- Restless legs syndrome
- Premature ejaculation
- Contraindications
- Pregnancy and lactation
- Labor and delivery
- Children
- Elderly
- Liver and kidney failure
- Side effects
- Dependence and withdrawal
- Overdose
- Interactions
- Pharmacology
- Mechanism of action
- Correspondence to effects
- Pharmacokinetics
- Chemistry
- Synthesis and stereoisomerism
- Detection in biological fluids
- Discrepant reports on natural agency
- Society and culture
- Formulations
- Patent history
- Legal status
- Misuse
- Research
- Veterinary medicine
- See also
- References
- Further reading
Tramadol, sold under the brand name Tramal among others, is an opioid pain medication and a serotonin–norepinephrine reuptake inhibitor (SNRI) used to treat moderate to severe pain. When taken by mouth in an immediate-release formulation, the onset of pain relief usually begins within an hour. It is also available by injection. It is available in combination with paracetamol (acetaminophen).
As is typical of opioids, common side effects include constipation, itchiness, and nausea. Serious side effects may include hallucinations, seizures, increased risk of serotonin syndrome, decreased alertness, and drug addiction. A change in dosage may be recommended in those with kidney or liver problems. It is not recommended in those who are at risk of suicide or in those who are pregnant. While not recommended in women who are breastfeeding, those who take a single dose should not generally have to stop breastfeeding. Tramadol is converted in the liver to O-desmethyltramadol (desmetramadol), an opioid with a stronger affinity for the μ-opioid receptor.