Tramadol

Chemistry

44 atoms · Conformer computed and published by PubChem.

Formula: C16H25NO2
Molar mass: 263.37 g/mol
IUPAC name: cis-(1R,2R)-2-[(dimethylamino)methyl]-1-(3-methoxyphenyl)cyclohexan-1-ol
InChIKey: TVYLLZQTGLZFBW-ZBFHGGJFSA-N

Chemistry from PubChem CID 33741.

Also known as

27203-92-5
Ralivia flashtab
Ralivia ER
Tramadon
cis-Tramadol
Biomadol
Contramid
Labesfal

Stereoisomers

4 distinct stereoisomers are registered for this structure.

Tramadol this area CID 33741
trans-Tramadol CID 63015
(-)-(S,S)-trans-Tramadol CID 667511
Tramadol, trans-(-)- CID 9813907
2-((Dimethylamino)methyl)-1-(3-methoxyphenyl)cyclohexanol mixture CID 5523

Sold as the racemate, and unusually both enantiomers earn their place: (+)-tramadol and its M1 metabolite carry the opioid action and serotonin reuptake inhibition, while (−)-tramadol inhibits noradrenaline reuptake. Separating them would not give you a better tramadol, it would give you two different and weaker drugs.

Photographs

Loose green-and-yellow tramadol 50 mg capsules beside their part-used foil blister strip, the two-tone gelatin capsule form common outside the US.

Glass 2 mL ampoule of Tramadol Stada injection solution, 100 mg tramadol hydrochloride, ringed with blue and green identification bands at the neck.

Swedish retail pack of Tramadol Aurobindo 50 mg hard capsules: teal-and-white carton over a silver blister card printed with the product name on every pocket.

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