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Thebaine (paramorphine), also known as codeine methyl enol ether, is an opiate alkaloid, its name coming from the Greek Θῆβαι, Thēbai (Thebes), an ancient city in Upper Egypt. A minor constituent of opium , thebaine is chemically similar to both morphine and codeine , but has stimulatory rather than depressant effects.
The structure of morphine is not particularly complex, however the electrostatic polarization of adjacent bonded atoms does not alternate uniformly throughout the structure. This "dissonant connectivity" makes bond formation more difficult and therefore significantly complicates any synthetic strategy that is applied to this family of molecules ...
Codeine Chemical structure of morphine. Opiates belong to the large biosynthetic group of benzylisoquinoline alkaloids, and are so named because they are naturally occurring alkaloids found in the opium poppy. The major psychoactive opiates are morphine, codeine, and thebaine.
General structure of a Bentley compound with an ethano-bridge (single bond) General structure of a Bentley compound with an etheno-bridge (double bond) The Bentley compounds are a class of semi-synthetic opioids that were first synthesized by K. W. Bentley by Diels-Alder reaction of thebaine with various dienophiles.
The definition of "opioid" was later refined to refer to substances that have morphine-like activities that are mediated by the activation of opioid receptors. One modern pharmacology textbook states: "the term opioid applies to all agonists and antagonists with morphine-like activity, and also the naturally occurring and synthetic opioid ...
Thebaine 6-O-demethylase (EC 1.14.11.31, T6ODM) is an enzyme with systematic name thebaine,2-oxoglutarate:oxygen oxidoreductase (6-O-demethylating). [1] This enzyme catalyses the following chemical reaction
Most alkaloids contain oxygen in their molecular structure; those compounds are usually colorless crystals at ambient conditions. Oxygen-free alkaloids, such as nicotine [160] or coniine, [36] are typically volatile, colorless, oily liquids. [161] Some alkaloids are colored, like berberine (yellow) and sanguinarine (orange). [161]
Chemical structure of morphine. The benzylisoquinoline backbone is shown in green. Morphine structure showing its standard ring lettering and carbon numbering system [citation needed] Same structure, but in a three-dimensional perspective. Morphine is a benzylisoquinoline alkaloid with two additional ring closures. [106]