Tramadol Chemistry

Characteristics

Structurally, tramadol closely resembles a stripped down version of codeine. Both codeine and tramadol share the 3-methyl ether group, and each compounds are metabolized alongside the identical hepatic pathway and mechanism to the stronger opioid, phenol agonist analogs. For codeine, that is morphine, and for tramadol, it's the O-desmethyltramadol.

Comparability with related substances
Structurally, tapentadol is the closest chemical relative of tramadol in medical use. Tapentadol is also an opioid, but not like each tramadol and venlafaxine, tapentadol represents only one stereoisomer and is the weaker of the two, when it comes to opioid effect. Each tramadol and venlafaxine are racemic mixtures. Structurally, tapentadol additionally differs from tramadol in being a phenol, and not an ether. Additionally, each tramadol and venlafaxine incorporate a cyclohexyl moiety, attached on to the aromatic, while tapentadol lacks this feature. In reality, the closest structural chemical entity to tapentadol in medical use is the over-the-counter drug phenylephrine. Both share a meta phenol, connected to a straight chain hydrocarbon. In each circumstances, the hydrocarbon terminates in an amine.

Synthesis and stereoisomerism

The chemical synthesis of tramadol is described within the literature. Tramadol [2-(dimethylaminomethyl)-1-(3-methoxyphenyl)cyclohexanol] has two stereogenic facilities at the cyclohexane ring. Thus, 2-(dimethylaminomethyl)-1-(3-methoxyphenyl)cyclohexanol might exist in 4 totally different configurational types:


 
(1R,2R)-Tramadol     (1S,2S)-Tramadol
 
(1R,2S)-Tramadol     (1S,2R)-Tramadol

•     (1R,2R)-isomer
•     (1S,2S)-isomer
•     (1R,2S)-isomer
•     (1S,2R)-isomer

The synthetic pathway results in the racemate (1:1 combination) of (1R,2R)-isomer and the (1S,2S)-isomer as the main products. Minor amounts of the racemic mixture of the (1R,2S)-isomer and the (1S,2R)-isomer are formed as well. The isolation of the (1R,2R)-isomer and the (1S,2S)-isomer from the diastereomeric minor racemate [(1R,2S)-isomer and (1S,2R)-isomer] is realized by the recrystallization of the hydrochlorides. The drug tramadol is a racemate of the hydrochlorides of the (1R,2R)-(+)- and the (1S,2S)-(-)-enantiomers. The resolution of the racemate [(1R,2R)-(+)-isomer / (1S,2S)-(-)-isomer] was described using (R)-(-)- or (S)-(+)-mandelic acid. This process does not discover industrial software, since tramadol is used as a racemate, regardless of known different physiological results of the (1R,2R)- and (1S,2S)-isomers, as a result of the racemate showed increased analgesic activity than both enantiomer in animals and in humans.

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