Chemical substance record

Tramadol

27203-92-5C₁₆H₂₅NO₂263.375 g/mol

Organic/Inorganic Small MoleculeChEBI source record

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. — ChEBI

Safety references

Safety documents & references

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Identity & molecular properties

Source-linked values

CAS number	27203-92-5	ChEBI ↗
Molecular formula	C₁₆H₂₅NO₂	ChEBI ↗
Molar mass	263.375 g/mol	ChEBI ↗
Monoisotopic mass	263.18853 Da	ChEBI ↗
Formal charge	0	ChEBI ↗
ChEBI identifier	CHEBI:9648	ChEBI ↗

Names & structural identifiers

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Source preferred name

tramadol

IUPAC name

rac-(1R,2R)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol

Names & synonyms

rac-(1R,2R)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanoltramadolum

Names are supplied by ChEBI. Trade names and related synonyms may describe a broader product context.

Classification & relationships

ChEBI ontology

racemateChEBI parent class · 60911 ↗

Roles recorded in ChEBI

antidepressantanalgesicopioid analgesicantineoplastic agentadrenergic uptake inhibitorxenobioticserotonergic antagonistmuscarinic antagonistnicotinic antagonistserotonin uptake inhibitor

Database role annotations describe reported biological or chemical roles; they are not product approvals or recommendations for use.

Mass ↔ amount of substance

Calculated from sourced mass

Amount

Input unit

Equivalent amount

0.00379687 mol

Uses 263.375 g/mol from ChEBI. Assumes the substance described by this record; no purity or concentration correction is applied.

Elemental composition

Theoretical mass fractions

C

Carbon · 16 atoms

72.97%

O

Oxygen · 2 atoms

12.15%

H

Hydrogen · 25 atoms

9.57%

N

Nitrogen · 1 atom

5.32%

Calculated theoretical mass fractions from the reported formula and PubChem periodic-table atomic masses. These are not assay or purity results.

Research & patent references

Selected source associations

Tramadol enhances urethral continence function through µ-opioid receptors in rats. ↗Neurourology and urodynamics · 2013 Jan · PMID 22674657

Tramadol and hypoglycaemia: comparison with other step 2 analgesic drugs. ↗British journal of clinical pharmacology · 2013 Apr · PMID 22943675

GB997399 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

US3652589 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

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Sources & record history

Checked 27 Sep 2026

Identity, formula, mass, synonyms & ontologyEMBL-EBI ChEBI · CHEBI:9648

Release 255, 9 September 2026. ChEBI three-star (manually annotated) source entry. View original record ↗ · CC BY 4.0

PubCAS formats source data, connects references and computes explicitly labelled conversions. CAS cross-references are supplied by ChEBI; they do not constitute CAS verification or endorsement.

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