| Identification | More | [Name]
Hexahydroisonicotinamide | [CAS]
39546-32-2 | [Synonyms]
4-PIPERIDINECARBOXAMIDE
HEXAHYDROISONICOTINAMIDE
ISONIPECOTAMIDE
LABOTEST-BB LT00848032
PIPERIDINE-4-CARBOXAMIDE
TIMTEC-BB SBB004237
Isonipecotinamide
Isonipecotamide,98%
4-Piperazine-D9-carboxamide
Isonipectoamide
PIPERIDINE-4-CARBALDEHYDE
Hexahydroisonicotinamide, Isonipecotamide | [EINECS(EC#)]
254-501-6 | [Molecular Formula]
C6H12N2O | [MDL Number]
MFCD00038012 | [Molecular Weight]
128.17 | [MOL File]
39546-32-2.mol |
| Chemical Properties | Back Directory | [Appearance]
WHITE TO LIGHT YELLOW CRYSTALLINE POWDER | [Melting point ]
145-148 °C(lit.)
| [Boiling point ]
237.61°C (rough estimate) | [density ]
1.0754 (rough estimate) | [refractive index ]
1.4880 (estimate) | [storage temp. ]
Keep in dark place,Inert atmosphere,Room temperature | [solubility ]
DMSO (Sparingly), Methanol (Slightly) | [form ]
Crystalline Powder | [pka]
16.48±0.20(Predicted) | [color ]
White to light yellow | [Water Solubility ]
Soluble in water. | [Sensitive ]
Hygroscopic | [BRN ]
112554 | [Stability:]
Hygroscopic | [InChI]
1S/C6H12N2O/c7-6(9)5-1-3-8-4-2-5/h5,8H,1-4H2,(H2,7,9) | [InChIKey]
DPBWFNDFMCCGGJ-UHFFFAOYSA-N | [SMILES]
NC(=O)C1CCNCC1 | [LogP]
-0.88 | [CAS DataBase Reference]
39546-32-2(CAS DataBase Reference) | [EPA Substance Registry System]
39546-32-2(EPA Substance) |
| Questions And Answer | Back Directory | [Synthesis]
For the synthesis of Isonipecotamide, conventional synthetic methods include: 1) Starting from 4-carboxamide pyridine (isoniacin), Isonipecotamide is obtained through complete hydrogenation of the pyridine ring. Commonly used transition metal catalysts include cobalt, rhodium, ruthenium, palladium, nickel, etc. Like other hydrogenation reactions, the reaction is generally very efficient and yields are high, usually without the need for column chromatography purification. However, interestingly, there are also reports that Isonipecotamide can be reversed to isoniacin via dehydrogenation in the presence of palladium. 
|
| Safety Data | Back Directory | [Symbol(GHS) ]
GHS07 | [Signal word ]
Warning | [Hazard statements ]
H315-H319-H335 | [Precautionary statements ]
P261-P264-P271-P280-P302+P352-P305+P351+P338 | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [Hazard Note ]
Irritant | [TSCA ]
Yes | [REACH Registrations]
Active | [HS Code ]
29339900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
WHITE TO LIGHT YELLOW CRYSTALLINE POWDER | [Uses]
Anesthetic, analgesic, antimicrobial and cooling agent for prevention or treatment of skin irritation.
| [Uses]
Reactant for synthesis of:• ;Survival motor neuron (SMN) protein modulators1• ;Diaminotriazine hNav1.7 inhibitors2• ;Heteroalicyclic carboxamidines as inhibitors of inducible nitric oxide synthase3• ;Orally available naphthyridine protein kinase D inhibitors4• ;Phosphodiesterase 5 inhibitors5Reactant for identification of small molecular inhibitors of importin-β mediated nublear import6 | [Application]
Isonipecotamide is an important substrate for organic synthesis reactions and can be used to prepare a wide range of inhibitors:
(1) Dual inhibitors of thrombin and cholinesterase with therapeutic potential for Alzheimer's disease[1].
(2) 5-HT receptor inhibitors, based on Isonipecotamide synthesised piperidine carboxamide derivatives showing signs of decreasing 5-HT levels alone while increasing dopamine levels, with antidepressant drug effects[2].
(3) Reversible inhibitors of coagulation factor Xa (fXa) and thrombin (thr) (cmpds 1-3), which have the ability to impede the infection of VERO cells with SARS-CoV-2, with cmpds3 showing a significant inhibitory effect on SARS-CoV-2 infection (~30%) at lower concentrations (3-50 μM)[3]. | [Definition]
ChEBI: 4-Piperidine carboxamide is a piperidinecarboxamide. | [References]
[1] ROSA PURGATORIO. First-in-Class Isonipecotamide-Based Thrombin and Cholinesterase Dual Inhibitors with Potential for Alzheimer Disease.[J]. Molecules, 2021. DOI:10.3390/molecules26175208.
[2] SHAMIM AKHTAR. Behavioral and neurochemical profile of some novel phenacyl based isonipecotamide derivatives.[J]. Pakistan journal of pharmaceutical sciences, 2012.
[3] FLAVIO DE MAIO. Evaluation of Novel Guanidino-Containing Isonipecotamide Inhibitors of Blood Coagulation Factors against SARS-CoV-2 Virus Infection.[J]. Viruses-Basel, 2022. DOI:10.3390/v14081730.
|
|
| Company Name: |
J & K SCIENTIFIC LTD.
|
| Telephone: |
18210857532 18210857532 |
| Website: |
https://www.jkchemical.com |
| Company Name: |
Alfa Aesar
|
| Telephone: |
400-6106006 |
| Website: |
http://chemicals.thermofisher.cn |
| Company Name: |
Energy Chemical
|
| Telephone: |
400-0056266 |
| Website: |
www.energy-chemical.com |
| Company Name: |
Jia Xing Isenchem Co.,Ltd
|
| Telephone: |
0573-85285100 18627885956 |
| Website: |
https://www.chemicalbook.com/ShowSupplierProductsList14265/0_EN.htm |
|