297-90-5

Usage

Uses

racephedrine.

Purification Methods

Crystallise it from MeOH or aqueous EtOH. The hydrochloride has m 176-177o. The hydrobromide has m 200-201o when recrystallised from EtOH/Et2O. [Sneider & Hellerbach Helv Chim Acta 33 1446 1950, Beilstein 21 III/IV 100.]

InChI:InChI=1/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3/t14-,16+,17+/m0/s1

Upstream product

• 67596-84-3 (+)-2-methyl-1-(4-methoxy)benzyl-1,2,3,4,5,6,7,8-hexahydroisoquinoline 
• 50-00-0 formaldehyd 
• 1531-12-0 norlevorphanol 
• 125-68-8 dextromethorphan hydrobromide 
• 125-72-4 levorphanol tartrate 
• 38969-65-2 1-(p-methoxybenzyl)-2-methyl-1,2,3,4,5,6,7,8-octahydroisoquinoline 
• 125-70-2 levomethorphan 
• 860371-36-4 1-(4-methoxy-benzyl)-2-methyl-octahydro-isoquinolin-4a-ol 
• 67553-46-2 (+/-)-4-(2-methyl-1,2,3,4,5,6,7,8-octahydro-[1]isoquinolylmethyl)-phenol 
• 98237-33-3 1-(4-Methoxybenzyl)-2-methyl-5,6,7,8-tetrahydroisochinoliniumiodide 
• 51072-36-7 (+)-1-(p-methoxybenzyl)-1,2,3,4,5,6,7,8-octahydroisoquinoline 
• 63477-92-9 1-(4-methoxy-benzyl)-octahydro-isoquinolin-4a-ol 
• 3399-73-3 2-(1-cyclohexenyl)ethylamine 
• 77-07-6 racemorphan 

Downstream Products

• 125-70-2 levomethorphan 
• 125-72-4 levorphanol tartrate 
• 67562-52-1 (-)-3-(m-methoxy)phenoxy-N-methylmorphinan 
• 67562-69-0 (-)-3-(m-Fluoro)phenoxy-N-methylmorphinan 
• 67562-77-0 (-)-3-phenoxy-N-methylmorphinan oxalate 
• 109596-70-5 C₁₇H₂₃NO₂ 
• 1210893-63-2 C₁₆H₂₁NO₂ 
• 1210893-59-6 C₁₇H₂₃NO₂ 
• 1531-12-0 norlevorphanol 

Relevant academic research and scientific papers

METHODS FOR PREPARING LEVORPHANOL AND RELATED COMPOUNDS, AND COMPOSITIONS THEREOF

A method for producing substantially pure levorphanol and related compounds, when compared to the conventional process, is provided. In particular, a method for producing substantially pure levorphanol tartrate dihydrate is described. Also described are compositions comprising levorphanol and related compounds, particularly compositions comprising levorphanol tartrate dihydrate, levomethorphan, and norlevorphanol in which the levomethorphan and norlevorphanol are present in the composition in reduced levels.

Retrorsine, but not monocrotaline, is a mechanism-based inactivator of P450 3A4

Retrorsine (RTS) and monocrotaline (MCT) cause severe toxicities via P450-mediated metabolic activation. The screening of mechanism-based inhibitors showed RTS inactivated 3A4 in the presence of NADPH. Unlike RTS, MCT failed to inhibit P450 3A4 and other enzymes tested. Further studies showed the loss of P450 3A4 activity occurred in a time- and concentration-dependent way, which was not recovered after dialysis. Dextromethorphan, a P450 3A4 substrate, protected the enzyme from the inactivation. Exogenous nucleophile glutathione (GSH) and reactive oxygen species scavengers catalase and superoxide dismutase did not protect P450 3A4 from the inactivation. GSH trapping experiments showed both P450 3A4 and 2C19 converted RTS and MCT to the corresponding electrophilic metabolites which could be trapped by GSH to form 7-GSH-DHP conjugate. We conclude that RTS and MCT are metabolically activated by P450 3A4 and 2C19, and that RTS, but not MCT, is a mechanism-based inactivator of P450 3A4.

PRODRUGS AND METHODS OF MAKING AND USING THE SAME

Prodrugs of parent drugs and methods of making and using the same are described. The prodrugs comprise an amine-containing parent drug moiety and a prodrug moiety, such as methoxyphosphonic acid or ethoxyphosphonic acid. The prodrugs may be employed in therapy for the treatment of various indications, such as pain, and in methods of decreasing the abuse potential of abuse-prone drugs and/or delaying the onset of parent drug activity and/or prolonging parent drug activity as compared to administration of a parent drug.

Crystalline Forms of Levorphanol

The present invention relates to novel crystalline polymorphic forms of levorphanol including hydrated, solvated, and non-hydrated (non-solvated) forms. The invention also describes methods of preparing the various polymorphic forms. The present invention also relates to pharmaceutical compositions containing crystalline polymorphs of levorphanol, as well as methods of relieving pain by administering the pharmaceutical compositions.

PROCESS FOR THE PRODUCTION OF LEVORPHANOL AND RELATED COMPOUNDS

A process for the production of morphinans with higher purity and yield, when compared to the conventional process, is described. Specifically, the process may be used to prepare levorphanol, levorphanol tartrate, and levorphanol tartrate dihydrate in high yields and substantially free from several process impurities.

Combination of selected opioids with muscarine antagonists for treating urinary incontinence

Active compound combinations of compounds of group A, particularly opioids, and compounds of group B, particularly anti-muscarine agents and other substances suitable for treatment of an increased urge to urinate or urinary incontinence. Related pharmaceutical formulations and methods of treatment of an increased urge to urinate or urinary incontinence are also provided.

Anticonvulsant effects of new morphinan derivatives

We synthesized a series of compounds that are modified in positions 3 and 17 of the morphinan ring system, with the intention of developing ideal anticonvulsant agents. We examined the effects of these compounds on kainic acid (KA)-induced seizures, and on locomotor patterns in rats. We found that compounds 5, 6, and 8 exhibit novel anticonvulsant effects, with negligible psychotropic effects.

Dextrorphan. Note II. Preparation of dextrorphan citrate

Preparation of destrorphan citrate, a very soluble salt in water, in described. This salt may be used in oral composition with anti-tussive activity. Structural date are reported about 1H-NMR, 13C-NMR, COSY.

Synthesis and Evaluation of 3-Substituted 17-Methylmorphinan Analogs as Potential Anticonvulsant Agents

Dextromethorphan (1, (+)-3-methoxy-17-methylmorphinan) demonstrates anticonvulsant activity in a variety of in vitro and in vivo models of convulsive action.It is well known that 1 is metabolized to its phenolic derivative dextrorphan (2) and this metabolite is also a potent anticonvulsant.A series of (+)-3-substituted-17-methylmorphinans, which are structurally similar to 1 but are either not expected to be metabolized to 2 or might do so at a reduced rate, as compared to 1, were prepared.Three analogs, 5 ((+)-3-amino-17-methylmorphinan), 14 ((+)-3-ethoxy-17-methylmorphinan), and 15 ((+)-3-(2-propoxy)-17-methylmorphinan were found to possess potent anticonvulsant activity with full efficacy (ED50 25, 5.6, and 3.9 mg/kg, sc, respectively) in the rat supramaximal electroshock (MES) test.Binding potencies of these compounds to receptor sites labeled with 3H>dextromethorphan (3H>1), in rat brain and guinea pig brain subcellular fractions, and 3H>thienylcyclohexylpiperidine (TCP) and 3H>glycine in rat brain, were determined.Most of the analogs displaced 3H>1 from its binding sites, with compounds 14 (IC50 0.42 μM) and 15 (IC50 0.88 μM having equivalent potencies to 1 (IC50 0.59 μM), in rat brain, and no appreciable activity at the 3H>TCP or 3H>glycine-labeled sites.Compound 5 did not bind with appreciable activity to the 3H>1 site, in rat brain, but did bind to the 3H>TCP site with lower potency than the parent 1 (IC50 7.8 and 2.0 μM, respectively).The mechanism of anticonvulsant action of these agents is not clear although it appears that interaction at the 3H>1 sites may be involved.