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35920-39-9

35920-39-9 structure
35920-39-9 structure
  • Name: NECA
  • Chemical Name: N-ethyl-5'-carboxamidoadenosine
  • CAS Number: 35920-39-9
  • Molecular Formula: C12H16N6O4
  • Molecular Weight: 308.293
  • Catalog: Biochemical Nucleoside drugs Nucleoside intermediate
  • Create Date: 2018-05-11 08:00:00
  • Modify Date: 2024-01-12 18:56:21
  • 5'-N-Ethylcarboxamidoadenosine (NECA) is a nonselective adenosine receptor agonist.

Name N-ethyl-5'-carboxamidoadenosine
Synonyms (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
Description 5'-N-Ethylcarboxamidoadenosine (NECA) is a nonselective adenosine receptor agonist.
Related Catalog
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.

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.

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
Symbol GHS06
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
HS Code 2934999090
Summary 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%