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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.
Morphine. Synthesis of morphine-like alkaloids in chemistry describes the total synthesis of the natural morphinan class of alkaloids that includes codeine, morphine, oripavine, and thebaine and the closely related semisynthetic analogs methorphan, buprenorphine, hydromorphone, hydrocodone, isocodeine, naltrexone, nalbuphine, oxymorphone, oxycodone, and naloxone.
Oripavine is an opioid and the major metabolite of thebaine.It is the precursor to the semi-synthetic compounds etorphine and buprenorphine.Although this chemical compound has analgesic potency comparable to morphine, it is not used clinically due to severe adverse effects and a low therapeutic index.
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.
Morphinan is the prototype chemical structure of a large chemical class of psychoactive drugs, consisting of opiate analgesics, cough suppressants, and dissociative hallucinogens, among others. Typical examples include compounds such as morphine, codeine, and dextromethorphan (DXM).
Some synthetic compounds of similar structure may also be termed alkaloids. [2] Alkaloids are produced by a large variety of organisms including bacteria, fungi, plants, and animals. [3] They can be purified from crude extracts of these organisms by acid-base extraction, or solvent extractions followed by silica-gel column chromatography. [4]
Salutaridinol can be converted in two reaction steps to the morphine precursor thebaine. The first step is an esterification of the hydroxyl group previously reduced in the conversion of salutaridine to salutaridinol with acetyl-CoA. This step is mediated by the enzyme salutaridinol 7-O-acetyltransferase.