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N,N-Diethylnicotinamide

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Name

N,N-Diethylnicotinamide

EINECS 200-418-5
CAS No. 59-26-7 Density 1.06
PSA 33.20000 LogP 1.56360
Solubility >=10g/100mLat23C Melting Point 24-26
Formula C10H14 N2 O Boiling Point 296-300
Molecular Weight 178.234 Flash Point 141.1°C
Transport Information N/A Appearance clear colorless to yellow liquid
Safety Poison by ingestion, intravenous, intraperitoneal, and subcutaneous routes. When heated to decomposition it emits toxic fumes of NOx. Risk Codes R23/24/25;
Molecular Structure Molecular Structure of 59-26-7 (N,N-DIETHYLNICOTINAMIDE) Hazard Symbols T
Synonyms

Nicotinamide,N,N-diethyl- (8CI);3-(N,N-Diethylcarbamoyl)pyridine;Anacardone;Anacordone;Astrocar;Canfodiamina;Carbamidal;Cardamine;Cardiamid;Cardiamide;Cardiamine;Cardimon;Coracon;Coractiv N;Coramine;Coramine (pharmaceutical);Cordiamin;Cordiamine;Corediol;Cormed;Cormid;Cormotyl;Cornotone;Corvin;Corvitol;Corvotone;Diethylnicotinamide;Dynacoryl;Ecoran;Eucoran;Kordiamin;N,N-Diethyl-3-pyridinecarboxamide;N,N-Diethylnicotinamide;NSC130820;NSC 169863;NSC 62103;Ni-Cor;Niamine;Nicamide;Nicetamide;Nicethamide;Nicorine;Nicotinic acid diethylamide;Nikardin;Niketamide;Niketamine;Nikethamide;Niketharol;Nikethyl;Nikorin;Niquetamide;Percoral;Pyricardyl;Pyridine-3-carboxydiethylamide;Pyridine-3-carboxylic aciddiethylamide;Reformin;Rehormin;Salvacard;Sancora;Solyacord;Stimulin;Ventramine;

Article Data 47

N,N-Diethylnicotinamide Synthetic route

626-55-1

3-Bromopyridine

201230-82-2

carbon monoxide

109-89-7

diethylamine

59-26-7

N,N-diethylnicotinamide

Conditions
ConditionsYield
With potassium carbonate; bis[2-(diphenylphosphino)phenyl] ether In toluene at 105℃; under 3000.3 Torr; for 12h;92%
With (1,3,5-triaza-7-phosphaadamantan-1-ium-1-yl)butane-1-sulfonate; palladium diacetate; triethylamine In N,N-dimethyl-formamide at 20 - 60℃; under 2068.65 Torr; for 24h; Inert atmosphere; Autoclave; chemoselective reaction;92%
With palladium diacetate; sodium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In toluene at 100℃; for 16h; Sealed tube;75%
59-67-6

nicotinic acid

617-84-5

N-formyldiethylamine

59-26-7

N,N-diethylnicotinamide

Conditions
ConditionsYield
With hydrogenchloride; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In 1,4-dioxane at 120℃; for 33h;92%
20165-96-2

3-(N,N-diethylcarbamoyl)pyridine 1-oxide

59-26-7

N,N-diethylnicotinamide

Conditions
ConditionsYield
With (4,4′-di-tert-butyl-2,2′-bipyridine)bis[(2-pyridinyl)phenyl]iridium(III) hexafluorophosphate; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate In acetonitrile at 20℃; for 2.5h; Inert atmosphere; Irradiation; chemoselective reaction;92%
59-67-6

nicotinic acid

2283-11-6

hexaethylphosphoric triamide

59-26-7

N,N-diethylnicotinamide

Conditions
ConditionsYield
at 210℃; for 1h;88%
93-60-7

methyl 3-pyridinecarboxylate

109-89-7

diethylamine

59-26-7

N,N-diethylnicotinamide

Conditions
ConditionsYield
Stage #1: diethylamine With n-butyllithium In tetrahydrofuran at -78 - 0℃; for 0.833333h;
Stage #2: methyl 3-pyridinecarboxylate In tetrahydrofuran at -78 - 20℃; for 2h;
84%
potassium tert-butylate at 285℃; under 22502.3 Torr; for 0.0116667h; autoclave; Industry scale; Microwave irradiation;
626-55-1

3-Bromopyridine

67-66-3

chloroform

109-89-7

diethylamine

59-26-7

N,N-diethylnicotinamide

Conditions
ConditionsYield
With cesiumhydroxide monohydrate; palladium diacetate; bis[2-(diphenylphosphino)phenyl] ether In toluene at 80℃; for 24h; Glovebox; Inert atmosphere; Sealed tube;79%
59-67-6

nicotinic acid

109-89-7

diethylamine

59-26-7

N,N-diethylnicotinamide

Conditions
ConditionsYield
Stage #1: nicotinic acid With niobium pentachloride In 1,4-dioxane
Stage #2: diethylamine In 1,4-dioxane at 45 - 50℃; for 12h;
73%
With phosphorus pentoxide
With phosphorus pentoxide; benzene
With trichlorophosphate
With N,N'-ethylenethiourea; bis(trichloromethyl) carbonate at 70℃; for 1h; Temperature; Reagent/catalyst; Green chemistry;
59-67-6

nicotinic acid

660-68-4

diethyl amine hydrochloride

59-26-7

N,N-diethylnicotinamide

Conditions
ConditionsYield
With triethylamine at 20℃; for 0.0166667h;72%
With silica gel; triethylamine; p-toluenesulfonyl chloride at 20℃; for 0.0166667h;70%
With phosphorus pentachloride
201230-82-2

carbon monoxide

1692-25-7

3-pyridylboronic acid

121-44-8

triethylamine

59-26-7

N,N-diethylnicotinamide

Conditions
ConditionsYield
With copper(l) iodide; oxygen; palladium dichloride In acetonitrile at 100℃; under 1520.1 Torr; for 12h; Autoclave; High pressure;62%
6972-69-6

N,N-dimethylnicotinamide

816-43-3

lithium diethylamide

A

77924-13-1

N,N-Dimethyl-4-(pyridine-3-carbonyl)-nicotinamide

B

59-26-7

N,N-diethylnicotinamide

Conditions
ConditionsYield
In diethyl ether for 5h; Ambient temperature;A 6%
B 60%

N,N-Diethylnicotinamide Specification

The N,N-Diethylnicotinamide, with the CAS registry number 59-26-7, is also known as 3-Pyridinecarboxamide,N,N-diethyl-;Nikethamide. It belongs to the product categories of Nitrogen cyclic compounds;Heterocyclic Compounds.This chemical's molecular formula is C10H14N2O and molecular weight is 178.23 .Its EINECS number is 200-418-5. What's more,Its systematic name is N,N-Diethylnicotinamide.It is Clear light yellow viscous liquid or crystalline solid. Slightly bitter taste followed by a faint sensation of the warmth. N,N-Diethylnicotinamide was used in the mid-1900s as a medical countermeasure against tranquilizer overdoses, before the advent of endotracheal intubation and positive-pressure lung expansion.It is a central nervous system stimulant. It was formerly used in the treatment of barbiturate overdose but is now considered to be of no value for such purposes and may be dangerous.

Physical properties about N,N-Diethylnicotinamide are:
(1)ACD/LogP: 0.923; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.92; (4)ACD/LogD (pH 7.4): 0.92; (5)ACD/BCF (pH 5.5): 2.93; (6)ACD/BCF (pH 7.4): 2.96; (7)ACD/KOC (pH 5.5): 74.85; (8)ACD/KOC (pH 7.4): 75.72; (9)#H bond acceptors: 3; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 3; (12)Index of Refraction: 1.52; (13)Molar Refractivity: 51.992 cm3; (14)Molar Volume: 170.961 cm3; (15)Surface Tension: 40.6370010375977 dyne/cm; (16)Density: 1.043 g/cm3 ; (17)Flash Point: 141.13 °C; (18)Enthalpy of Vaporization: 53.789 kJ/mol; (19)Boiling Point: 297.999 °C at 760 mmHg; (20)Vapour Pressure: 0.00100000004749745 mmHg at 25°C;

Safety Information of N,N-Diethylnicotinamide:
The N,N-Diethylnicotinamide is toxic by inhalation, in contact with skin and if swallowed .It is irritating to eyes, respiratory system and skin.In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.When you use it ,wear suitable protective clothing, gloves and eye/face protection.In case of accident or if you feel unwell, seek medical advice immediately (show label where possible).

You can still convert the following datas into molecular structure:
(1)SMILES:O=C(N(CC)CC)c1cccnc1;
(2)Std. InChI:InChI=1S/C10H14N2O/c1-3-12(4-2)10(13)9-6-5-7-11-8-9/h5-8H,3-4H2,1-2H3;
(3)Std. InChIKey:NCYVXEGFNDZQCU-UHFFFAOYSA-N.

The toxicity data of N,N-Diethylnicotinamide as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 174mg/kg (174mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal of Pharmacology and Experimental Therapeutics. Vol. 128, Pg. 176, 1960.
mouse LD50 intravenous 180mg/kg (180mg/kg)   Schweizerische Medizinische Wochenschrift. Vol. 85, Pg. 305, 1955.
mouse LD50 oral 188mg/kg (188mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: REGIDITY
Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 1, Pg. 423, 1964.
mouse LD50 subcutaneous 200mg/kg (200mg/kg)   Bollettino Chimico Farmaceutico. Vol. 111, Pg. 293, 1972.
mouse LD50 unreported 288mg/kg (288mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 53, Pg. 2S, 1957.
rabbit LDLo intravenous 150mg/kg (150mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Journal of Pharmacology and Experimental Therapeutics. Vol. 66, Pg. 260, 1939.
rabbit LDLo subcutaneous 300mg/kg (300mg/kg)   Klinische Wochenscrift. Vol. 12, Pg. 1860, 1933.
rat LD50 intraperitoneal 272mg/kg (272mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Proceedings of the European Society for the Study of Drug Toxicity. Vol. 4, Pg. 132, 1964.
rat LD50 intravenous 191mg/kg (191mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 173, 1973.
rat LD50 subcutaneous 240mg/kg (240mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES Proceedings of the Society for Experimental Biology and Medicine. Vol. 62, Pg. 19, 1946.

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