NECA

Names

[ Name ]:
NECA

[Synonym ]:
(2S,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-N-ethyl-3,4-dihydroxytetrahydrofuran-2-carboxamide (non-preferred name)
(2S,3S,4R,5R)-5-(6-Amino-9H-purin-9-yl)-N-ethyl-3,4-dihydroxytetrahydro-2-furancarboxamide (non-preferred name)
5’-Ethylcarboxamido Adenosine
MFCD00069195
5'-Ethylcarboxamido Adenosine
1-(6-AMINO-9H-PURIN-9-YL)-1-DEOXY-N-ETHYL-β-D-RIBOFURANURONAMIDE
β-D-Ribofuranuronamide, 1-(6-amino-9H-purin-9-yl)-1-deoxy-N-ethyl-
5'-(N-Ethylcarboxamido)adenosine
NECA

Biological Activity

[Description]:

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

[Related Catalog]:

Signaling Pathways >> GPCR/G Protein >> Adenosine Receptor

Research Areas >> Cancer

Research Areas >> Metabolic Disease

[Target]

Adenosine receptor[1]

[In Vivo]

After the administration of 5'-N-Ethylcarboxamidoadenosine (NECA), the mean number of cocaine infusions obtained per session is decreased significantly in a dose-dependent manner [5'-N-Ethylcarboxamidoadenosine (NECA): F(4,12)=14.9; P<0.001]. The administration of 5'-N-Ethylcarboxamidoadenosine (NECA) [F(4,12)=16.1; P<0.001] results in a significant increase in latencies above values obtained for vehicle treatment[1]. Daily i.p. injection of 5'-N-Ethylcarboxamidoadenosine (NECA) at 0.3 mg/kg/day for two weeks reduces malondialdehyde (MDA) levels in diabetic rats, but does not affect control rats. Daily treatment with NECA (0.3 mg/kg/day, i.p. for two weeks) reduces diabetes-induced gene expression of tumor necrosis factor (TNF)-α and interleukin (IL)-18 in diabetic rats, but does not affect control rats. Daily i.p. injection of 5'-N-Ethylcarboxamidoadenosine (NECA) at 0.3 mg/kg/day for two weeks also blocks the activation of JNK MAPK in diabetic rats, but does not affect control rats[2].

[Animal admin]

Male Wistar rats are used in this experiment. These animals range in weight between 350 and 425 g. They are housed individually in hanging wire cages under a 12-h light/dark cycle. The effects of 5'-N-Ethylcarboxamidoadenosine (NECA) are tested in four rats. In the experiment, either 5'-N-Ethylcarboxamidoadenosine (NECA) (5, 7.5, 10, 20 μg/kg) or vehicle (saline) is administered intraperitoneally 15 min prior to the start of test sessions. 5'-N-Ethylcarboxamidoadenosine (NECA) is administered following a random order crossover design. In most cases, animals are tested twice with the same dose[1].

[References]

[1]. Knapp CM, et al. Adenosine agonists CGS 21680 and NECA inhibit the initiation of cocaine self-administration. Pharmacol Biochem Behav. 2001 Apr;68(4):797-803.

[2]. Elsherbiny NM, et al. Reno-protective effect of NECA in diabetic nephropathy: implication of IL-18 and ICAM-1. Eur Cytokine Netw. 2012 Jul-Sep;23(3):78-86.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.9±0.1 g/cm3

[ Melting Point ]:
229-231ºC

[ Molecular Formula ]:
C₁₂H₁₆N₆O₄

[ Molecular Weight ]:
308.293

[ Exact Mass ]:
308.123291

[ PSA ]:
148.41000

[ LogP ]:
-0.48

[ Index of Refraction ]:
1.829

[ Water Solubility ]:
45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: 0.2 mg/mL Solutions may be stored for several days at 4?#x00b0;C.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VJ2232000

CHEMICAL NAME :: Ribofuranuronamide, 1-(6-amino-9H-purin-9-yl)-1-deoxy-N-ethyl-, hemihydrate

CAS REGISTRY NUMBER :: 35920-39-9

LAST UPDATED :: 199512

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C12-H16-N6-O4.1/2H2-O

MOLECULAR WEIGHT :: 317.35

WISWESSER LINE NOTATION :: T56 BN DN FN HNJ IZ D- BT5OTJ CQ DQ EVM2 &QH 1/2

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 23,313,1980

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 500 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 23,313,1980

Safety Information

[ Symbol ]:

GHS06

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300

[ Precautionary Statements ]:
P264-P301 + P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
T+: Very toxic;

[ Risk Phrases ]:
R28

[ Safety Phrases ]:
22-26-36-45

[ RIDADR ]:
UN 2811 6.1/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
VJ2232000

[ Packaging Group ]:
I

[ Hazard Class ]:
6.1(a)

[ HS Code ]:
2934999090

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2934999090

[ Summary ]:
2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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