Isonipecotamide Chemical Properties

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

InChIKey

DPBWFNDFMCCGGJ-UHFFFAOYSA-N

LogP

-0.88

CAS DataBase Reference

39546-32-2(CAS DataBase Reference)

EPA Substance Registry System

4-Piperidinecarboxamide (39546-32-2)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-36

WGK Germany 

3

Hazard Note 

Irritant

TSCA 

Yes

HS Code 

29339900

MSDS

• Language:English Provider:Hexahydroisonicotinamide
• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

Isonipecotamide Usage And Synthesis

Chemical Properties

WHITE TO LIGHT YELLOW CRYSTALLINE POWDER

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

Uses

Isonipecotamide is used as a reactant for the preparation of Survival motor neuron (SMN) protein modulators, orally available naphthyridine protein kinase D inhibitors and heteroalicyclic carboxamidines as inhibitors of inducible nitric oxide synthase. It is also used to prepare phosphodiesterase 5 inhibitors. It is also used as a reactant for identification of small molecular inhibitors of importin-beta mediated nuclear import. It is also used as a fluorenylmethyloxycarbonyl - deprotection agent in organic synthesis.

Uses

Anesthetic, analgesic, antimicrobial and cooling agent for prevention or treatment of skin irritation.

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.

Isonipecotamide(39546-32-2)Related Product Information

• piperidine-N-carbaldehyde,PIPERIDINE-1-CARBALDEHYDE,N-FORMYL PIPERIDINE PIPERIDINE-1-CARBALDEHYDE
• 4-Benzyloxycarbonylaminopiperidine Hydrochloride
• DL-Pipecolinic acid
• Piperazine-2-carboxylic acid dihydrochloride
• 3-CBZ-AMINOPIPERIDINE HCL
• tert-Butyl 1-piperazinecarboxylate
• PIPERIDIN-3-ONE HYDROCHLORIDE
• Azido-PEG1-CH2CO2H
• 4-HYDROXY-3-METHYLBENZOIC ACID
• Benzyl 4-hydroxy-1-piperidinecarboxylate
• 4-Pyrimidinecarboxylic acid
• Isonipecotic acid
• 4,4-Piperidinediol hydrochloride
• PIPERIDINE-4-CARBOXYLIC ACID ETHYL ESTER HYDROCHLORIDE
• 4-PIPERIDINECARBOXYLIC ACID T-BUTYL ESTER HCL
• Methyl 4-piperidinecarboxylate
• 4-Piperidinemethanol
• Methyl isonipecotate