Tramadol
Athanor · official
C16H25NO2 · 263.37 g/mol
IUPAC name: 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol
Also called Ultram, Tramal, opioid
Names and identifiers
- IUPAC name
- 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol
- Synonyms
- Ultram, Tramal, opioid
+ 37 more
2-[(Dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexanol, CHEBI:75722, 2-((Dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexanol, RefChem:1060573, 2-[(DIMETHYLAMINO)METHYL]-1-(3-METHOXYPHENYL)CYCLOHEXAN-1-OL, 2-Dimethylaminomethyl-1-(m-methoxyphenyl)cyclohexanol, cis,trans-(+-)-L 201, Cyclohexanol, 2-(dimethylaminomethyl)-1-(m-methoxyphenyl)-, NIOSH/GV8924900, GV89249000, 2-((Dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexan-1-ol, (1R,2S)-2-[(Dimethylamino)Methyl]-1-(3-Methoxyphenyl)Cyclohexanol Hydrochloride, Cyclohexanol, 2-((dimethylamino)methyl)-1-(m-methoxyphenyl)-, (+-)-cis,trans-, EINECS 220-831-4, Adolonta, Maxitram, Tilodol, E265, Tramadol Impurity 4, (+)-Tramadol-d6, SCHEMBL57496, tramadol (not stereospecific), GTPL8286, SCHEMBL6944556, CHEMBL1237044, DTXSID00860388, Cyclohexanol, 2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)-, GHA28958, GHA28959, AKOS022507395, FT28359, FM172554, FT178076, DB-226678, DS-015928, NS00083054, L000985
- Molecular formula
- C16H25NO2
- Empirical formula
- C16H25NO2
- Molecular weight
- 263.37 g/mol
- Exact mass
- 263.18853
- CAS number
- 27203-92-5
- PubChem CID
- 5523
- Canonical SMILES
- CN(C)CC1CCCCC1(C2=CC(=CC=C2)OC)O
- Isomeric SMILES
- CN(C)CC1CCCCC1(C2=CC(=CC=C2)OC)O
- InChI
- 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
- InChIKey
- TVYLLZQTGLZFBW-UHFFFAOYSA-N
- Molfile
Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.
Calculated
- Heavy atoms
- 19
- Rings
- 2
- Aromatic rings
- 1
- Fraction sp³ carbons (Fsp3)
- 0.62
- H-bond donors
- 1
- H-bond acceptors
- 3
- Rotatable bonds
- 4
- TPSA (Ų)
- 32.7
- Formal charge
- 0
- XLogP3
- 2.6 PubChem
- Complexity
- 282 PubChem
- Stereocenters
- 0 defined, 2 undefinedCIP: C9: undefined · C15: undefined
- Double-bond geometry
- None specified
- Point group
- C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)
Elemental analysis
- C72.97%
- H9.57%
- N5.32%
- O12.15%
Isotope pattern
Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.
Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.
Predicted
- log P
- 2.63 Crippen (Wildman and Crippen 1999)
- log S (water solubility)
- -3.1 ESOL (Delaney 2004), log mol/L
- Synthetic accessibility
- 3.02 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)
Drug-likeness: Lipinski’s rule of five
- Molecular weight ≤ 500: 263.38
- log P ≤ 5 (Crippen): 2.63
- H-bond donors ≤ 5: 1
- H-bond acceptors ≤ 10: 3
Passes all four rules.
¹³C NMR shifts, predicted
Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.
Safety
No GHS hazard classification was found in the sources.
Always read the supplier’s safety data sheet before working with it.
Spectra
- GC-MSNIST Mass Spectrometry Data Center · NIST Mass Spectrometry Data Center · NIST Mass Spectrometry Data Center · NIST Mass Spectrometry Data Center · NIST Mass Spectrometry Data Center · SpectraBase (GC)
- MS-MSHuman Metabolome Database (HMDB) (Positive) · Human Metabolome Database (HMDB) (Positive) · NIST Mass Spectrometry Data Center (IT/ion trap) · NIST Mass Spectrometry Data Center (IT/ion trap)
- LC-MSMassBank Europe (6550 Q-TOF (Agilent Technologies) · LC-ESI-QTOF · POSITIVE) · MassBank Europe (6550 Q-TOF (Agilent Technologies) · LC-ESI-QTOF · POSITIVE) · MassBank Europe (6550 Q-TOF (Agilent Technologies) · LC-ESI-QTOF · POSITIVE) · MassBank of North America (MoNA) (6550 Q-TOF (Agilent Technologies) · LC-ESI-QTOF · positive) · MassBank of North America (MoNA) (6550 Q-TOF (Agilent Technologies) · LC-ESI-QTOF · positive) · MassBank of North America (MoNA) (6550 Q-TOF (Agilent Technologies) · LC-ESI-QTOF · positive)
Experimental spectra held by these sources; each link opens the source's own record.
Literature
Reading PubChem, OpenAlex and GSRS…
Bioactivity
Reading ChEMBL…
References
- [1]NIST Mass Spectrometry Data Center · Linked only · via PubChem · retrieved 2026-10-14
- [2]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
- [3]Human Metabolome Database (HMDB) · Linked only · via PubChem · retrieved 2026-10-14
- [4]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
- [5]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
- ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
- ·Literature on PubChem
Data last updated 2026-10-14.