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NECA

NECA structure

CAS No:
35920-39-9
Formula:
C12H16N6O4
Chemical Name:
NECA
Synonyms:
5'-N6-Ethylcarboxamidoadenosine;5'-ETHYLCARBOXAMIDOADENOSINE;1-(6-AMINO-9H-PURIN-9-YL)-1-DEOXY-N-ETHYL-BETA-D-RIBOFURANURONAMIDE;1-(6-amino-9h-purin-9-yl)-1-deoxy-n-ethylribofuranuronamidehemihydrate;1-(6-amino-9h-purin-9-yl)-1-deoxy-n-ethyl-ribofuranuronamidhemihydrate;5’-n(sup6)-ethylcarboxamidoadenosinehemihydrate;5’-n-ethylcarboxamidoadenosinehemihydrate;adenosine-5’-(n-ethyl)carboxamidehemihydrate
Categories:
Biochemical Engineering > Saccharides

Description

5'-N-Ethylcarboxamidoadenosine (NECA) is a nonselective adenosine receptor agonist.

N-ethyl-5'-carboxamidoadenosine is a derivative of adenosine in which the 5'-hydroxymethyl group is replaced by an N-ethylcarboxamido group. It has a role as an adenosine A1 receptor agonist, an adenosine A2A receptor agonist, an EC 3.1.4.* (phosphoric diester hydrolase) inhibitor, an antineoplastic agent and a vasodilator agent. It is a member of adenosines and a monocarboxylic acid amide. It derives from an adenosine.|A stable adenosine A1 and A2 receptor agonist. Experimentally, it inhibits cAMP and cGMP phosphodiesterase activity.

White Solid

A cell-permeable adenosine analog that acts a potent non-selective agonist of adenosine receptors (Ki= 14 nM, 20 nM, 2.4 μM and 6.2 nM for A1, A2A, A2B, A3, respectively). Increases intracellular cAMP production (EC50= 3.1 μM in A2Bexpressing CHO cells). Shown to increase glucagon release in a dose-dependent manner and inhibit insulin release at low concentrations. Although at higher concentration some insulin release is observed. Also, displays a wide range adenosine-dependent effects, such as blocking platelet aggregation and inhibiting DNA synthesis. When administered at reperfusion, it is shown reduce infarction and block the formation of the mitochondrial permeability transition pore by activating p70S6 kinase.

NECA Basic Attributes

Molecular Weight：

308.29

Exact Mass：

308.29

Color/Form：

white

HScode：

29349990

Characteristics

PSA：

148.41000

XLogP3：

-0.48

Appearance：

white powder

Density：

1.87±0.1 g/cm3(Predicted)

Melting Point：

229-231°C

Refractive Index：

1.829

Water Solubility：

45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.2mg/mL (Solutions may be stored for several days at 4 °C.)DMSO: 14mg/mL (Solutions may be stored for several days at 4 °C.)0.1 M HCl: 3.4mg/mL (Solutions may be stored for several days at 4 °C.)H2O: insolubleethanol: soluble (Solutions may be stored for several days at 4 °C.)

Storage Conditions：

2-8°C

Toxicity：

Oral-mouse LD50: 5 mg/kg; peritoneal-mouse LD50: 0.5 mg/kg

Flammability characteristics：

Flammable; burning releases toxic nitrogen oxide fumes

PKA：

12.93±0.70(Predicted)

Critical Temperature & Pressure：

2-8°C

Safety Information

Packing level：

Hazard category：

6.1(a)

Transport codes：

UN 2811 6.1/PG 2

wgk germany：

hazard class code：

T+

safety instructions：

22-26-36-45

RTECS Number：

VJ2232000

Marks：

T+

Storage features：

Store at +4°C

Precautionary statement(s)：

P264-P301 + P310

Hazard Statements：

RIDADR：

UN 2811 6.1/PG 2

GHS Classification：

|Danger|H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]|P264, P270, P301+P310, P321, P330, P405, and P501|Aggregated GHS information provided by 38 companies from 1 notifications to the ECHA C&L Inventory.

Toxicity

Toxicity class：

most toxic

Drug Information

MeSH：

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)|Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

MeSH Entry Terms：

5' N Ethylcarboxamidoadenosine

NECA Use and Manufacturing

A potent adenosine receptor agonist.Inhibits platelet aggregation and is centrally active in vivo

Potent adenosine receptor agonist with some affinity at A1 and A2 receptors

5′-(N-Ethylcarboxamido)adenosine has been used:for the purification of human adenosine A2Areceptor (A2AR) in decylmaltoside (DM)to determine nonspecific binding of adenosine receptorsto investigate adenosine 2B receptor (RA2B) mechanism of action by competition assay

Computed Properties

Molecular Weight:308.29
XLogP3:-0.7
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:3
Exact Mass:308.12330301
Monoisotopic Mass:308.12330301
Topological Polar Surface Area:148
Heavy Atom Count:22
Complexity:426
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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NECA

CAS No.: 35920-39-9

Content: 99.00%

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Guide of NECA

Description
Basic Attributes
Characteristics
Safety Information
Toxicity
Drug Information
Use and Manufacturing
Computed Properties
Recommended Suppliers
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