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A1755

Sigma-Aldrich

Aminophylline

≥98%, powder

Synonym(s):

(Theophylline)2 · Ethylenediamine, 3,7-Dihydro-1,3-dimethyl-1H-purine-2,6-dione, cmpd. with 1,2-ethanediamine (2:1), Theophylline hemi(ethylenediamine) complex

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About This Item

Empirical Formula (Hill Notation):
C7H8N4O2 · 0.5C2H8N2
CAS Number:
317-34-0
Molecular Weight:
210.21
EC Number:
206-264-5
MDL number:
MFCD00013221
UNSPSC Code:
41106305
PubChem Substance ID:
24277691
NACRES:
NA.77

Assay

≥98%

form

powder

color

white to off-white

solubility

H2O: 50 mg/mL (solutions should be freshly prepared.)
alcohol: insoluble

storage temp.

−20°C

SMILES string

NCCN.CN1C(=O)N(C)c2nc[nH]c2C1=O.CN3C(=O)N(C)c4nc[nH]c4C3=O

InChI

1S/2C7H8N4O2.C2H8N2/c2*1-10-5-4(8-3-9-5)6(12)11(2)7(10)13;3-1-2-4/h2*3H,1-2H3,(H,8,9);1-4H2

InChI key

FQPFAHBPWDRTLU-UHFFFAOYSA-N

Gene Information

human ... ADORA1(134) , ADORA2A(135) , ADORA2B(136) , ADORA3(140) , PDE3A(5139) , PDE3B(5140) , PDE4A(5141) , PDE4B(5142) , PDE4C(5143) , PDE4D(5144)

Application

Aminophylline has been used:
  • as a positive control in the selective inhibitor of nuclear export, KPT-350 zebrafish dosing experiments
  • as a positive control for the determination of the spasmolytic activity of C. aeruginosa extracts
  • as a phosphodiesterase (PDE) inhibitor in inhibitor studies to quantify its potency to inhibit PDE4A1A and PDE3A enzyme in an assay

Biochem/physiol Actions

Aminophylline is a methylxanthine compound containing theophylline andethylenediamine in a ratio of 2:1. It acts as a bronchodilator and is used to treat chronic lung diseases like asthma, bronchitis, or emphysema.
Non-selective phosphodiesterase (PDE) inhibitor. Antiepileptic drug

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301

Hazard Classifications

Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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Antiasthmatic effect of Curcuma aeruginosa extract on isolated organ of the trachea
Marliana E, et al.
F1000Research (2018)
Saniyya Khan et al.
Journal of biomolecular structure & dynamics, 39(3), 970-976 (2020-01-30)
Aminophylline (Am) is a methylxanthine compound clinically applied for chronic lung diseases like asthma, bronchitis or emphysema. Chemically, it comprises theophylline and ethylenediamine in a ratio 2:1. For the widening of the therapeutic window of any class of drug or
K C Crisanti et al.
The American journal of physiology, 277(3 Pt 2), R829-R835 (1999-09-14)
In newborns and adults of a number of species, exposure to acute hypoxemia produces a "regulated" decrease in core temperature, the mechanism of which is unknown. The present experiments were carried out on chronically instrumented newborn (5-10 days of age;
Ram Manohar Basnet et al.
BMC pharmacology & toxicology, 18(1), 72-72 (2017-11-17)
Zebrafish embryos are emerging as a model for pharmacological and toxicological studies. We used zebrafish embryos to study the general toxicity and cardiovascular effects of eight methylxanthines: aminophylline, caffeine, diprophylline, doxofylline, etophylline, 3-isobutyl-1-methylxanthine (IBMX), pentoxifylline and theophylline. Microinjections of the
Danieli Barino Salinas et al.
Pediatric research, 87(1), 137-145 (2019-07-26)
There is a need to prognosticate the severity of cystic fibrosis (CF) detected by newborn screening (NBS) by early assessment of CF transmembrane conductance regulator (CFTR) protein function. We introduce novel instrumentation and protocol for evaluating CFTR activity as reflected
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