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467-04-9Relevant academic research and scientific papers
Identification of fluorinated (R)-(?)-aporphine derivatives as potent and selective ligands at serotonin 5-HT2C receptor
Xu, Yulong,Sromek, Anna W.,Neumeyer, John L.
, p. 230 - 233 (2019)
A series of novel aporphine derivatives were synthesized for initial screening at the 5-HT2 receptor subtypes. Among them, Compounds 11a and 11b were identified as potent 5-HT2C hit ligands with high selectivity over other 5-HT2 receptor subtypes. Molecular docking study revealed that compounds 11a and 11b formed two key interactions with the binding site of 5-HT2C receptor, including a salt-bridge to D3.32 and a H-bond interaction with N6.55.
Synthesis and dopamine receptor affinities of N-Alkyl-11-hydroxy-2- methoxynoraporphines: N-Alkyl substituents determine D1 versus D2 receptor selectivity
Si, Yu-Gui,Gardner, Matthew P.,Tarazi, Frank I.,Baldessarini, Ross J.,Neumeyer, John L.
, p. 983 - 987 (2008)
We developed a procedure to synthesize a series of N-alkyl-2-methoxy-11- hydroxynoraporphines from thebaine and evaluated their binding affinities at dopamine D1 and D2 receptors in rat forebrain tissue. At D2 receptors, the most potent 10,11-catechol-aporphine was (R)-(-)-2-methoxy-N-n-propylnorapomorphine (D2, Ki = 1.3 nM; D1, Ki = 6450 nM), and the most selective and potent 11-monohydroxy aporphine was (R)-(-)-2-methoxy-11-hydroxy-N-n-propylnoraporphine (D2, Ki = 44 nM; D1, Ki = 1690 nM). In contrast, the N-methyl congeners (R)-(-)-2-methoxy-11-hydroxy-N-methyl- aporphine (D1 vs D2, Ki = 46 vs 235 nM) showed higher D1 than D2 affinity, indicating that N-alkyl substituents have major effects on D2 affinity and D 2/D1 selectivity in such 2-methoxy-11-monohydroxy- substituted aporphines.
Synthesis and neuropharmacological evaluation of esters of R(-)-N-alkyl-11-hydroxy-2-methoxynoraporphines
Si, Yu-Gui,Choi, Yong-Kee,Gardner, Matthew P.,Tarazi, Frank I.,Baldessarini, Ross J.,Neumeyer, John L.
, p. 51 - 53 (2009)
We synthesized several esters of R(-)-N-alkyl-11-hydroxy-2-methoxynoraporphines, assessed their affinities at dopamine D1 and D2 receptors in rat forebrain tissue and quantified their effects on motor activity in normal adult male rats. Tested compounds displayed moderate to high affinities to D2 receptors but low affinities to D1 receptors. The most D2-potent (Ki = 18.9 nM) and selective novel agent (>529-fold vs D1 sites) was R(-)-2-methoxy-11-acetyloxy-N-n-propylnoraporphine (compound 4b). At moderate doses, the compound proved to have prolonged behavioral locomotor activity.
Synthesis and binding studies of 2-O- and 11-O-substituted N-alkylnoraporphines
Si, Yu-Gui,Gardner, Matthew P.,Tarazi, Frank I.,Baldessarini, Ross J.,Neumeyer, John L.
, p. 3971 - 3973 (2008)
We synthesized several novel 2-O- or 11-O-substituted N-alkylnoraporphines and assessed their affinities at dopamine D1 and D2, and serotonin 5-HT1A receptors in rat forebrain tissue. Tested compounds displayed moderate to high affinities to D2 receptors but low affinities to D1 and 5HT1A receptors. The findings accord with previous evidence of a lipophilic cavity on the surface of the D2 receptor to accommodate N-alkyl moieties of aporphines. The most D2-potent (Ki = 97 nM) and selective novel agent (>100-fold vs. D1 and 5-HT1A sites) was R(-)-2-(2-hydroxyethoxy)-11-hydroxy-N-n-propylnoraporphine (compound 11).
METHODS FOR THE PREPARATION OF HYDROMORPHONE
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Paragraph 0099; 0101, (2015/09/22)
The present application relates to methods for the preparation of morphine derivatives. In particular, the present application relates to methods for the preparation of hydromorphone from oripavine and oripavine from thebaine.
Conversion of thebaine to oripavine and other useful intermediates for the semisynthesis of opiate-derived agents: Synthesis of hydromorphone
Murphy, Brennan,Snajdr, Ivan,Machara, Ales,Endoma-Arias, Mary Ann A.,Stamatatos, Theocharis C.,Cox, D. Phillip,Hudlicky, Tomas
, p. 2679 - 2687 (2014/09/30)
Thebaine was converted to oripavine in three steps by employing two different modes of protection of the diene moiety; as an iron tricarbonyl complex and as a Diels-Alder adduct with thioformyl cyanide. The two C-ring-protected thebaine derivatives were subjected to 3-O-demethylation by four different protocols, providing oripavine derivatives, which yielded oripavine after deprotection. Oripavine was then converted to hydromorphone by a three-step process of ketalization, hydrogenation, and deprotection, without the isolation of intermediates.
METHOD OF PREPARING BUPRENORPHINE
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Paragraph 0143; 0154, (2014/09/03)
An improved process for preparing buprenorphine and a method for increasing the yield of buprenorphine or a derivative thereof.
Rat CYP2D2, not 2D1, is functionally conserved with human CYP2D6 in endogenous morphine formation
Grobe, Nadja,Kutchan, Toni M.,Zenk, Meinhart H.
experimental part, p. 1749 - 1753 (2012/08/29)
The assumption that CYP2D1 is the corresponding rat cytochrome to human CYP2D6 has been revisited using recombinant proteins in direct enzyme assays. CYP2D1 and 2D2 were incubated with known CYP2D6 substrates, the three morphine precursors thebaine, codeine and (R)-reticuline. Mass spectrometric analysis showed that rat CYP2D2, not 2D1, catalyzed the 3-O-demethylation reaction of thebaine and codeine. In addition, CYP2D2 incubated with (R)-reticuline generated four products corytuberine, pallidine, salutaridine and isoboldine while rat CYP2D1 was completely inactive. This intramolecular phenol-coupling reaction follows the same mechanism as observed for CYP2D6. Michaelis-Menten kinetic parameters revealed high catalytic efficiencies for rat CYP2D2. These findings suggest a critical evaluation of other commonly accepted, however untested, CYP2D1 substrates.
R-(-)-N-alkyl-11-hydroxy-10-hydroxymethyl- and 10-methyl-aporphines as 5-HT1A receptor ligands
Si, Yu-Gui,Gardner, Matthew P.,Tarazi, Frank I.,Baldessarini, Ross J.,Neumeyer, John L.
, p. 4128 - 4130 (2008/02/09)
Several N-substituted-11-hydroxy-10-hydroxymethyl- and 11-hydroxy-10-methylaporphines were synthesized and their binding affinities at dopamine D1 and D2 receptors and serotonin 5-HT1A and 5-HT2A receptors in rat forebrain tissue were evaluated. Tested compounds displayed moderate to high affinity to 5-HT1A receptors but low affinity to D1 and D2 receptors. The most potent novel 5-HT1A agent was R-(-)-N-methyl-10-hydroxymethyl-11-hydroxyaporphine.