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Tramadol

Tramadol (marketed as Ultram, and as generics) is an opioid pain medication used to treat moderate to moderately severe pain. When taken as an immediate-release oral formulation, the onset of pain relief usually occurs within about an hour. It has two different mechanisms. First, it binds to the μ-opioid receptor. Second, it inhibits the reuptake of serotonin and norepinephrine.

Serious side effects may include seizures, increased risk of serotonin syndrome, decreased alertness, and drug addiction. The risk of serotonin syndrome appears to be low. Common side effects include: constipation, itchiness and nausea, among others. A change in dosage may be recommended in those with kidney or liver problems. Its use is not recommended in women who are breastfeeding or those who are at risk of suicide.

Tramadol is marketed as a racemic mixture of both R- and S-stereoisomers. This is because the two isomers complement each other's analgesic activity. It is often combined with paracetamol (acetaminophen) as this is known to improve the efficacy of tramadol in relieving pain. Tramadol is metabolised to O-desmethyltramadol, which is a more potent opioid. It is of the benzenoid class.

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Product Description



2-[(Dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol


Clinical data
Trade names Ryzolt, Tramal, Ultram
AHFS/Drugs.com monograph
MedlinePlus a695011
Licence data US FDA:link
Pregnancy category
  • AU: C
  • US: C (Risk not ruled out)
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: Class C – Schedule 3 CD
  • US: Schedule IV
  • ℞ (Prescription only)
Dependence liability Present[1]
Routes of administration Oral, IV, IM, rectal


Bioavailability 70–75% (oral), 77% (rectal), 100% (IM)[2]
Protein binding 20%[3]
Metabolism Liver-mediated demethylation and glucuronidation via CYP2D6 & CYP3A4[2][3]
Biological half-life 6.3 ± 1.4 hr[3]
Excretion Urine (95%)[4]


CAS Number 27203-92-5 
ATC code N02AX02
PubChem CID: 33741
DrugBank DB00193 
ChemSpider 31105 
UNII 39J1LGJ30J 
KEGG D08623 
ChEBI CHEBI:9648 
ChEMBL CHEMBL1066 


Formula C16H25NO2
Molecular mass 263.4 g/mol

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