16499-30-2

Basic information

• Product Name: 1-(dimethylamino)cyclohexanecarbonitrile
• Synonyms: 1-(dimethylamino)cyclohexanecarbonitrile;1-(dimethylamino)cyclohexanecarbonitrile(SALTDATA: FREE);1-(diMethylaMino)cyclohexane-1-carbonitrile;NSC 525355
• CAS NO: 16499-30-2
• Molecular Formula: C₉H₁₆N₂
• Molecular Weight: 152.24
• Mol File: 16499-30-2.mol

Chemical Properties

• Melting Point: 30℃
• Boiling Point: 112-113℃ (17 Torr)
• Flash Point: 95.7°C
• Appearance: /
• Density: 0.95g/cm³
• Vapor Pressure: 0.0253mmHg at 25°C
• Refractive Index: 1.482
• Storage Temp.: 2-8°C
• PKA: 5.38±0.70(Predicted)
• CAS DataBase Reference: 1-(dimethylamino)cyclohexanecarbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(dimethylamino)cyclohexanecarbonitrile(16499-30-2)
• EPA Substance Registry System: 1-(dimethylamino)cyclohexanecarbonitrile(16499-30-2)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 16499-30-2(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
1-(dimethylamino)cyclohexanecarbonitrile is used as a reagent for the synthesis of various organic compounds. Its presence in the reaction mixture facilitates the formation of new carbon-carbon or carbon-heteroatom bonds, which are crucial for the construction of complex molecular structures. The reactivity of the cyano group allows for further functional group transformations, making it a versatile building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
1-(dimethylamino)cyclohexanecarbonitrile is used as an intermediate in the synthesis of certain pharmaceutical compounds. Its unique structural features enable the development of new drug candidates with potential therapeutic applications. The cyano group can be further modified to introduce additional functional groups, which may enhance the biological activity or improve the pharmacokinetic properties of the resulting drug molecules.
Used in Agrochemical Industry:
1-(dimethylamino)cyclohexanecarbonitrile is used as a starting material in the preparation of agrochemicals, such as pesticides and herbicides. The cyano group can be converted into other functional groups that exhibit pesticidal or herbicidal activity, contributing to the development of more effective and environmentally friendly crop protection products.
Used in Specialty Chemicals:
1-(dimethylamino)cyclohexanecarbonitrile is used as a precursor in the production of specialty chemicals, such as dyes, pigments, and polymers. The versatility of the cyano group allows for the synthesis of a wide range of chemical structures with diverse properties, which can be tailored for specific applications in various industries.

InChI:InChI=1/C9H16N2/c1-11(2)9(8-10)6-4-3-5-7-9/h3-7H2,1-2H3

Upstream product

• 74-90-8 hydrogen cyanide 
• 108-94-1 cyclohexanone 
• 124-40-3 dimethyl amine 
• 75-86-5 2-hydroxy-2-methylpropanenitrile 
• 931-97-5 1-hydroxy-1-cyclohexanecarbonitrile 
• 506-59-2 N,N-dimethylammonium chloride 
• 151-50-8 potassium cyanide 
• 7677-24-9 trimethylsilyl cyanide 

Downstream Products

• 63909-23-9 (1-Cyano-cyclohexyl)-dimethylamino-acetic acid ethyl ester 
• 55154-30-8 AH 7921 
• 41806-04-6 1-dimethylaminocyclohexylamide 
• 130648-82-7 2-diphenylphosphino-1-cyanocyclohexane 
• 130648-82-7 2-diphenylphosphino-1-cyanocyclohexane 
• 41806-09-1 1-aminomethyl‐1‐cyclohexanedimethylamine 
• 2201-17-4 N,N-dimethyl-1-phenylcyclohexyl-1-amine 
• 42419-56-7 1-(4-bromophenylamino)cyclohexanecarbonitrile 
• 42419-57-8 1-diethylamino-1-cyclohexanecarbonitrile 
• 1855-63-6 cyclohex-1-enecarbonitrile 
• 42419-55-6 1-Heptylamino-cyclohexanecarbonitrile 
• 5259-69-8 1-(hydroxyamino)cyclohexanecarbonitrile 

Relevant articles and documents

Synthesis and pharmacological characterization of ethylenediamine synthetic opioids in human μ-opiate receptor 1 (OPRM1) expressing cells

Opioids are powerful analgesics acting via the human μ-opiate receptor (hMOR). Opioid use is associated with adverse effects such as tolerance, addiction, respiratory depression, and constipation. Two synthetic opioids, AH-7921 and U-47700 that were developed in the 1970s but never marketed, have recently appeared on the illegal drug market and in forensic toxicology reports. These agents were initially characterized for their analgesic activity in rodents; however, their pharmacology at hMOR has not been delineated. Thus, we synthesized over 50 chemical analogs based on core AH-7921 and U-47700 structures to assess for their ability to couple to Gαi signaling and induce hMOR internalization. For both the AH-7921 and U-47700 analogs, the 3,4-dichlorobenzoyl substituents were the most potent with comparable EC50 values for inhibition of cAMP accumulation; 26.49?±?11.2?nmol L?1 and 8.8?±?4.9?nmol L?1, respectively. Despite similar potencies for Gαi coupling, these two compounds had strikingly different hMOR internalization efficacies: U-47700 (10?μmol L?1) induced ~25% hMOR internalization similar to DAMGO while AH-7921 (10?μmol L?1) induced ~5% hMOR internalization similar to morphine. In addition, the R, R enantiomer of U-47700 is significantly more potent than the S, S enantiomer at hMOR. In conclusion, these data suggest that U-47700 and AH-7921 analogs have high analgesic potential in humans, but with divergent receptor internalization profiles, suggesting that they may exhibit differences in clinical utility or abuse potential.

AH-7921 DETECTION

Antibodies, immunoassay methods and kits for the detection and determination of 3,4,-dichloro-N-[(1-(dimethylamino)cyclohexyl)methyl]benzamide and 3,4,-dichloro-N-[(1-(methylamino)cyclohexyl)methyl]benzamide, as well as the precursory immunogens, are described.

2-AMINO-1-PHENYLETHYLCARBOXAMIDE DERIVATIVES

The present invention relates to compounds of formula (I), or to salts or solvates thereof, their use in the manufacture of medicaments for treating neurological and neuropsychiatric disorders, in particular psychoses, dementia or attention deficit disorder. The invention further comprises processes to make these compounds and pharmaceutical formulations thereof. Formula (I) wherein R1 is a group selected from: Formulas (A), (B), (C)

Serotoninergic properties of new conformationally restricted benzamides

A new series of benzamides derived from metoclopramide have been synthesized, in which the vicinal carbon of the basic nitrogen atom of the ethyl chain is situated on the C3, C4, C5 and C6 rings. The diamino derivatives were prepared through Strecker's reaction from the corresponding ketones except for the cyclopropyl derivatives where 1-ethoxy-1-trimethylsiloxy cyclopropane was used as the starting material. The benzamides were prepared using the mixed anhydride method. They were tested in binding assays for D2, 5-HT3 and 5-HT4 receptors. The results show a marked increase in the selectivity and potency of these derivatives for 5-HT3 receptors with regard to metoclopramide (compound 1d: 5-HT3 K(i) = 9.03 nM; 5-HT4 K(i) > 5000; D2 K(i) > 5000). The influences of steric hindrance and hydrophobic properties on the affinity of benzamide derivatives for 5-HT3 receptors were also emphasized by these data. The X-ray crystal structure of compound 1d was compared with that of the minimal energy conformer of BRL 24682, a reference 5-HT3 receptor antagonist benzamide, determined using the Random Search program. Superimposition of the two structures showed a suitable fit between the pharmacophore groups previously determined to be important for 5-HT3 receptor antagonists. On the other hand, the hydrophobic parts of the basic moieties had different spatial occupancies.

Addition of diphenylphosphine to Michael-type olefins: the preparation of phosphine-nitrile and phosphine-ester ligands

The reactions of five Michael-type olefins with diphenylphosphine have been carried out. 1-Cyanocyclopentene, 1-cyanocyclohexene, and 4-t-butyl-1-cyanocyclohexene all provide the corresponding 2-diphenylphosphino-1-cyanocycloalkanes, and both methyl acrylate and ethyl methacrylate yield to corresponding 2-diphenylphosphinopropionates.For the products from 1-cyanocyclopentene and 1-cyanocyclohexene, 13C and 31P NMR data are consistent with the formation of both trans (Ph2P equatorial and CN axial) and cis (both Ph2P and CN equatorial) isomers.The morpholine amide of 3-diphenylphosphinopropionic acid has been obtained by treatment of methyl-3-diphenylphosphinopropionate with the dimethylaluminum adduct of morpholine.This phosphine, Ph2Pmorph, has been isolated as its palladium(II) complex, (Ph2Pmorph)2PdCl2.A phosphine-benzaldimine, Ph2P(CH2)3NC(H)C6H5, has been obtained by reacting Ph2P(CH2)3NH2, from the reduction of PhP(CH2)2CN, with benzaldehyde in the presence of molecular sieves.

A FAST N-SUBSTITUTED α-AMINONITRILE SYNTHESIS

A series of α-aminonitriles bearing various functionalities was prepared by reacting a neat mixture of an aldehyde or ketone, an amine and trimethylsilyl cyanide.The reaction was essentially complete in 5 minutes.

1-(3,4-DICHLOROBENZAMIDOMETHYL)-CYCLOHEXYLDIMETHYLAMINE

Compounds of the general formula I: EQU1 in which R1 - R4 which may be the same or different represent hydrogen atoms, or C1-6 straight or branched chain alkyl, alkenyl or alkynyl group or an alkyl group substituted by a cycloalkyl group, or represents a cycloalkyl, alkoxycarbonyl, aryl, arakyl, acyl (which includes anylsulphonyl) groups in which the alkyl group or the alkyl portion of the aralkyl group may be substituted with one or more hydroxy or esterified hydroxy groups and in which the aryl groups or the aryl portion of the acyl or aralkyl group may be substituted by one or more halogen atoms, alkyl groups, hydroxy groups, alkoxy groups, trifluoromethyl, nitro, amino or dialkylamino groups, and in which R5 - R8 which may be the same or different represent hydrogen atoms or alkyl groups except that not all groups may be hydrogen, or R5 and R6 or R7 and R8 together represent a carbonyl (=O) oxygen and in any of the pairs of groups R1 /R2, R3 /R4, R5 /R6 and R7 /R8 may represent a carbocyclic or heterocyclic ring system optionally substituted by lower alkyl or aryl groups, said ring being saturated or unsaturated. These compounds have utility as oral analgesics.