Tramadol

Tramadol
Clinical data
Pronunciation/ˈtræməˌdɒl/
Trade namesTramal, others
AHFS/Drugs.comMonograph
MedlinePlusa695011
License data
Pregnancy
category
  • AU: C
Routes of
administration
By mouth, intravenous, intramuscular, rectal
Drug class
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability68% (by mouth), 77% (rectal), 100% (IM)
Protein binding20%
MetabolismLiver-mediated demethylation and glucuronidation via CYP2D6 & CYP3A4
MetabolitesO-desmethyltramadol
N-desmethyltramadol
Onset of action< 1 hour (by mouth)
Elimination half-life6.3 ± 1.4 h
Duration of action6 hours
ExcretionUrine (95%)
Identifiers
  • 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.043.912
Chemical and physical data
FormulaC16H25NO2
Molar mass263.381 g·mol−1
3D model (JSmol)
Melting point180 to 181 °C (356 to 358 °F)
  • CN(C)C[C@H]1CCCC[C@@]1(C2=CC(=CC=C2)OC)O
  • 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 Y
  • Key:TVYLLZQTGLZFBW-ZBFHGGJFSA-N Y
 NY (what is this?)  (verify)

Tramadol, sold under the brand name Tramal among others, is an opioid pain medication and a serotonin–norepinephrine reuptake inhibitor (SNRI) used to treat moderately 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.

Tramadol was patented in 1972 and launched under the brand name Tramal in 1977 by the West German pharmaceutical company Grünenthal GmbH. In the mid-1990s, it was approved in the United Kingdom and the United States. It is available as a generic medication and marketed under many brand names worldwide. In 2022, it was the 55th most commonly prescribed medication in the United States, with more than 12 million prescriptions.