125-79-1

Basic information

• Product Name: 4-dimethylamino-2,2-diphenylvaleronitrile
• Synonyms: 4-dimethylamino-2,2-diphenylvaleronitrile;rac-2-Despropionyl 2-Cyano Methadone;rac-2-Despropionyl 2-Cyano Methadone (Methadone Nitrile);2,2-Diphenyl-4-(diMethylaMino)valeronitrile;NSC 2089;NSC 50382;4-(dimethylamino)-2,2-diphenylpentanenitrile;Methadone Impurity B
• CAS NO: 125-79-1
• Molecular Formula: C₁₉H₂₂N₂
• Molecular Weight: 278.39138
• EINECS: 204-755-9
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 125-79-1.mol

Chemical Properties

• Melting Point: 90-91 °C
• Boiling Point: 402.9°Cat760mmHg
• Flash Point: 165.9°C
• Appearance: /
• Density: 1.032g/cm³
• Vapor Pressure: 1.06E-06mmHg at 25°C
• Refractive Index: 1.554
• PKA: 8.89±0.50(Predicted)
• CAS DataBase Reference: 4-dimethylamino-2,2-diphenylvaleronitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-dimethylamino-2,2-diphenylvaleronitrile(125-79-1)
• EPA Substance Registry System: 4-dimethylamino-2,2-diphenylvaleronitrile(125-79-1)

Safety Data

• Hazardous Substances Data: 125-79-1(Hazardous Substances Data)

Usage

Chemical Properties

Light Brown Solid

Uses

Intermediate in the production of Methadone.

InChI:InChI=1/C19H22N2/c1-16(21(2)3)14-19(15-20,17-10-6-4-7-11-17)18-12-8-5-9-13-18/h4-13,16H,14H2,1-3H3

Upstream product

• 56-23-5 tetrachloromethane 
• 86-29-3 Diphenylacetonitrile 
• 865-47-4 potassium tert-butylate 
• 75-65-0 tert-butyl alcohol 
• 4584-49-0 (2-chloropropyl)dimethylamine hydrochloride 
• 108-14-5 2-chloro-1-dimethylaminopropane 
• 20985-42-6 4-Oxo-2,2-diphenylvaleronitril 
• 506-59-2 N,N-dimethylammonium chloride 
• 71-43-2 benzene 
• 140-29-4 phenylacetonitrile 
• 5798-79-8 bromo-phenyl-acetonitrile 
• 1438527-99-1 C₅H₁₂N⁽¹⁺⁾*Cl^(1-) 
• 182693-63-6 3-(2-Methyl-1,3-dioxolan-2-yl)-2,2-diphenylpropionitril 
• 53309-35-6 (2-chloro-1-methyl-ethyl)-dimethyl-amine 

Downstream Products

• 76-99-3 Methadone 
• 32443-35-9 5-dimethylamino-3,3-diphenyl-hexan-2-one 
• 24052-92-4 5-methyl-3,3-diphenyl-pyrrolidin-2-one-imine 
• 13957-55-6 recipavrin 
• 872807-71-1 1,N¹,N¹-trimethyl-3,3-diphenyl-butanediyldiamine 
• 62572-82-1 2-dimethylamino-4,4-diphenyl-nonan-5-one 
• 14474-50-1 6-dimethylamino-4,4-diphenyl-heptan-3-one-imine 
• 412282-67-8 1,5-dimethyl-3,3-diphenyl-pyrrolidin-2-ylideneamine 
• 5348-94-7 (+/-)-4-Dimethylamino-2,2-diphenylpentanoic acid 
• 60-46-8 aminopentamide 
• 7576-08-1 (S)-(+)-2,2-diphenyl-4-dimethylaminopentanenitrile 
• 7576-16-1 (R)-(-)-2,2-diphenyl-4-dimethylaminopentanenitrile 
• 110050-37-8 (+/-)-4-dimethylamino-2.2-diphenyl-valeric acid ethyl ester 
• 103193-25-5 (3-cyano-1-methyl-3,3-diphenyl-propyl)-trimethyl-ammonium; iodide 

Relevant articles and documents

COMPOSITIONS AND METHODS FOR THE TREATMENT OF SEVERE PAIN

The invention relates to the compounds of formula I or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula I, and methods for the treatment of severe pain may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of chronic pain, generalized pain disorders, leukemia, cancer, chronic pain, chemotherapy induced pain, epilepsy, migraine, neuropathic pain, post herpetic neuralgia, neuralgia, pain, drug addiction, detoxification of drugs, Alzheimer's disease, multiple sclerosis, multiple sclerosis, restless legs syndrome (RLS), cluster headache, depression, fibromyalgia, amyotrophic lateral sclerosis (ALS), convulsions, partial seizures, mood-stabilizing agent and bipolar disorder.

(R)-6-(DIMETHYLAMINO)-4,4-DIPHENYLHEPTAN-3-ONE

(R)-6-(dimethylamino)-4,4-diphenylheptan-3-one and a process to produce thereof.

COMPOSITIONS AND METHODS FOR THE TREATMENT OF SEVERE PAIN

The invention relates to the compounds of formula (I) or its pharmaceutical acceptable salts, as well as polymorphs, solvates, enantiomers, stereoisomers and hydrates thereof. The pharmaceutical compositions comprising an effective amount of compounds of formula (I), and methods for the treatment of severe pain may be formulated for oral, buccal, rectal, topical, transdermal, transmucosal, intravenous, parenteral administration, syrup, or injection. Such compositions may be used to treatment of chronic pain, generalized pain disorders, leukemia, cancer, chronic pain, chemotherapy induced pain, epilepsy, migraine, neuropathic pain, post herpetic neuralgia, neuralgia, pain, drug addiction, detoxification of drugs, Alzheimer's disease, multiple sclerosis, multiple sclerosis restless legs syndrome (RLS), cluster headache, depression, fibromyalgia, amyotrophic lateral sclerosis (ALS), convulsions, partial seizures, mood-stabilizing agent and bipolar disorder.

(R)-6-(DIMETHYLAMINO)-4,4-DIPHENYLHEPTAN-3-ONE

Methods for producing methadone and its resolution to produce (R)-6-dimethylamino-4,4-diphenylheptan-3-one ((R)- methadone). Such methods producing first the precursor compound 4-(dimethylamino)-2,2-diphenylpentanitrile. Oxidation of 4-(dimethylamino)-2,2-diphenylpentanitrile with ethyl magnesium halide and hydrolysis with of the complex to form 6-dimethylamino-4,4-diphenylheptan-3-one. Resolution to the (R)-isomer is effected by reaction with a bromocamphor salt. Once isolated the (R)-isomer is crystallised.

Considerations to the synthesis of methadone-nitrile as well as isomethadone-nitrile, and related compounds

The 2-chloro-1-dialkylamino-propanes 4a-d are reacted with diphenylacetonitrile under phase transfer conditions to give a mixture of the nitriles la-d and 2a-d. Both chloro-dialkylamino-1-phenyl-ethanes 7a-d and 8a-d lead to 4-dialkylamino-2,2,3-triphenyl-butyronitriles 6a-d.

Process for the preparation of optically active methadones in high enantiomeric purity

PCT No. PCT/GB97/01441 Sec. 371 Date Apr. 9, 1999 Sec. 102(e) Date Apr. 9, 1999 PCT Filed May 27, 1997 PCT Pub. No. WO97/45551 PCT Pub. Date Dec. 4, 1997A method of preparing optically active methadones comprises an enzymatic process for the resolution of 1-dialkyl-amino-2-propanol and conversion of the enantiomers to the optically active methadones in high enantiomeric purity.

Methadone derivatives and protein and polypeptide methadone derivative conjugates and labels

The present invention is directed to novel methadone derivatives which are synthesized for the covalent attachment to antigens (proteins or polypeptides) for the preparation of antibodies or receptors to methadone and methadone metabolites. The resulting novel antigens may be used for the production of antibodies or receptors using standard methods. Once generated, the antibodies or receptors and the novel derivatives which are covalently attached to proteins, polypeptides or labels may be used in the immunoassay process.

A novel approach to isomeric pure (±)-methadone

Alkylation of deprotonated diphenylacetonitrile (2) with an acetal of chloroacetone followed by acidic hydrolysis and reductive amination of the resulting ketonitrile 12 offered an easy access to the methadone precursor 3. By this pathway the formation of the undesired regioisomer 4 was avoided.

Methadone fluorescence polarization immunoassay

A fluorescence polarization immunoassay for detecting the presence of methadone in a test sample is provided, based upon competition between methadone and a fluorescently labeled tracer for the binding sites on an antibody specific for methadone. The concentration of methadone in the sample determines the amount of tracer that binds to the antibody. The amount of tracer-antibody complex formed can be quantitatively measured and is inversely proportional to the quantity of methadone in the sample. Tracers used as reagents and immunogens used to raise antibodies for use as reagents are also disclosed.

Synthesis and anticonvulsant screening of 3,3-diphenyl-2-pyrrolidone derivatives

Six derivatives of 3,3-diphenyl-2-pyrrolidone were synthesized and screened for anticonvulsant activity. The synthetic route involved a mono-N-demethylation of an intermediate N,N-dimethylaminonitrile with methyl chloroformate followed by cleavage of the carbamate group. Of the six derivatives, (±)-2-imino-1,5-dimethyl-3,3-diphenylpyrrolidine hydrochloride was effective in protecting mice against maximal electroshock (MES)-induced seizures at a 30-mg/kg dose level.