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: This review summarizes recent developments in the total synthesis of morphine alkaloids and some of the semisynthetic derivatives. The literature is covered for the period of 5 years after the publication of the last review in 2005. The syntheses that appeared in this period are covered in detail and are placed in the context of all syntheses of opiate alkaloids since the original one published by Gates in 1952. The introduction covers the historical aspects of total synthesis of these alkaloids. The synthesis of some of the medicinally useful derivatives is reviewed in the last section along with some of the methodology required for their preparation.
Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090, Vienna, Austria, firstname.lastname@example.org.
This article was published in the following journal.
Name: Topics in current chemistry
Conspectus We became interested in approaches to morphine in the early 1990s following our immersion into the new program on the enzymatic dihydroxylation of aromatics. Larry Kwart, a former classmate...
Morphinan alkaloids are the most powerful narcotic analgesics currently used to treat moderate to severe and chronic pain. The feasibility of morphinan synthesis in recombinant Saccharomyces cerevisia...
The gateway to morphine biosynthesis in opium poppy (Papaver somniferum) is the stereochemical inversion of (S)-reticuline since the enzyme yielding the first committed intermediate salutaridine is sp...
2-(Acylmethylene)pyrrolidine derivatives were synthesized via intermolecular decarbonylative Mannich reaction from various methyl ketones and 1-alkyl-1-pyrroliniums, generated in situ from 1-alkylprol...
Regioselective synthesis of 3-bromoquinoline derivatives was achieved via a formal [4+2]-cycloaddition between N-aryliminium ion, generated from arylmethyl azides, and 1-bromoalkynes. This method coul...
This study aims to compare the effect of spinal morphine between the dose 0.05 mg and 0.1 mg on the amount of morphine during the first 24 hours postoperative.
RATIONALE: Morphine that is inhaled may be more rapidly absorbed than morphine that is given by mouth. It is not yet known if inhaled morphine is more effective than morphine given by mout...
This is a randomized Phase II study testing the effectiveness of the combination of morphine and methadone versus morphine alone in relieving pain. A second goal is to further evaluate any...
RATIONALE: Morphine helps to relieve the pain associated with cancer surgery. Giving morphine in different ways may offer more pain relief. PURPOSE: This randomized clinical trial is stud...
Ketamine (an analgesic drug often associated with morphine in the treatment of Opioid Induced Hyperalgesia) is often mixed in Morphine PCA syringe. We make the hypothesis that ketamine adm...
Analogs or derivatives of morphine.
Morphine derivatives of the methanobenzazocine family that act as potent analgesics.
The principal alkaloid in opium and the prototype opiate analgesic and narcotic. Morphine has widespread effects in the central nervous system and on smooth muscle.
The air-dried exudate from the unripe seed capsule of the opium poppy, Papaver somniferum, or its variant, P. album. It contains a number of alkaloids, but only a few - MORPHINE; CODEINE; and PAPAVERINE - have clinical significance. Opium has been used as an analgesic, antitussive, antidiarrheal, and antispasmodic.
An opioid analgesic made from MORPHINE and used mainly as an analgesic. It has a shorter duration of action than morphine.