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Sigma-Aldrich

N-(3-Aminopropyl)methacrylamide hydrochloride

contains ≤1,000 ppm MEHQ as stabilizer, 98% (HPLC)

Synonym(s):

APMA

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About This Item

Empirical Formula (Hill Notation):
C7H14N2O · HCl
CAS Number:
72607-53-5
Molecular Weight:
178.66
MDL number:
MFCD00078257
UNSPSC Code:
12162002
PubChem Substance ID:
329764619
NACRES:
NA.23

assay

98% (HPLC)

form

powder

contains

≤1,000 ppm MEHQ as stabilizer

mp

123-128 °C

storage temp.

2-8°C

SMILES string

Cl.CC(=C)C(=O)NCCCN

InChI

1S/C7H14N2O.ClH/c1-6(2)7(10)9-5-3-4-8;/h1,3-5,8H2,2H3,(H,9,10);1H

InChI key

XHIRWEVPYCTARV-UHFFFAOYSA-N

General description

N-(3-Aminopropyl)methacrylamide hydrochloride (APMA) is an aminoalkyl methacrylamide which can be synthesized by adding 1,3-diaminopropane to 1,3-diaminopropane dihydrogen chloride solution and further mixing the solution with methacrylic anhydride and hydroquinone. It has a primary amine that provides attractive features such as pH-responsiveness, affinity for anionic drugs and conjugation for variety of chemical structures.

Application

APMA can be used in the preparation of copolymers and cross-linked miscellas for gene delivery, drug delivery and diagnostics applications.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H319

Hazard Classifications

Eye Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Facile synthesis of controlled-structure primary amine-based methacrylamide polymers via the reversible addition-fragmentation chain transfer process
Deng Z, et al.
Journal of Polymer Science Part A: Polymer Chemistry, 46(15), 4984-4996 (2008)
Gaurasundar M Conley et al.
Nature communications, 10(1), 2436-2436 (2019-06-06)
Thermosensitive microgels are widely studied hybrid systems combining properties of polymers and colloidal particles in a unique way. Due to their complex morphology, their interactions and packing, and consequentially the viscoelasticity of suspensions made from microgels, are still not fully
Preparation and characterization of narrow compositional distribution polyampholytes as potential biomaterials: Copolymers of N-(3-aminopropyl) methacrylamide hydrochloride (APM) and methacrylic acid (MAA)
Dubey A, et al.
Journal of Polymer Science Part A: Polymer Chemistry, 53(2), 353-365 (2015)
Polymer mediated peptide immobilization onto amino-containing N-isopropylacrylamide-styrene core-shell particles
Rossi S, et al.
Colloid and Polymer Science, 282(3), 215-222 (2004)
Michika Onoda et al.
Nature communications, 8, 15862-15862 (2017-07-14)
In the field of polymer science, many kinds of polymeric material systems that show a sol-gel transition have been created. However, most systems are unidirectional stimuli-responsive systems that require physical signals such as a change in temperature. Here, we report
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