Norepinephrine supplier | CasNO.51-41-2

Name
Norepinephrine
EINECS 200-096-6
CAS No. 51-41-2
Article Data12
CAS DataBase
Density 1.397 g/cm³
Solubility Soluble in alkali and dilute hydrochloric acid. Slightly soluble in water, ethanol and diethyl ether.
Melting Point 220-230 °C
Formula C₈H₁₁NO₃
Boiling Point 442.6 °C at 760 mmHg
Molecular Weight 169.18
Flash Point 221.5 °C
Transport Information UN 2811 6.1/PG 2
Appearance Off-white to tan solid
Safety 28-36/37-45-36/37/39-26-16
Risk Codes 26/27/28-34-11
Molecular Structure
Hazard Symbols T+,C,F
Synonyms 1,2-Benzenediol,4-(2-amino-1-hydroxyethyl)-, (R)-;Arterenol, l- (6CI);Benzyl alcohol, a-(aminomethyl)-3,4-dihydroxy-,(-)- (8CI);(-)-Arterenol;(-)-Noradrenaline;(-)-Norepinephrine;(-)-a-(Aminomethyl)protocatechuylalcohol;(R)-(-)-Norepinephrine;(R)-Noradrenaline;(R)-Norepinephrine;4-((1R)-2-Amino-1-hydroxyethyl)-1,2-benzenediol;Adrenor;Aktamin;Arterenol;Levoarterenol;Levonor;Levonorepinephrine;Levophed;Nor-Epirenan;Norartrinal;Sympathin E;l-1-(3,4-Dihydroxyphenyl)-2-aminoethanol;l-2-Amino-1-(3,4-dihydroxyphenyl)ethanol;l-3,4-Dihydroxyphenylethanolamine;l-Arterenol;
PSA 86.71000
LogP 0.79020

Synthetic route

: 499-61-6
arterenone

: 51-41-2
norepinephrine

Conditions

Conditions	Yield
Stage #1: arterenone With (-)-diisopinocampheylboron chloride In tert-butyl methyl ether at -25 - -20℃; for 3h; Inert atmosphere; Stage #2: With hydrogenchloride In tert-butyl methyl ether; water at 25℃; for 1.5h; Catalytic behavior; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	70.3%

: 104819-57-0, 104873-30-5, 104873-31-6
R-(+)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-hydroxy-2-amido-ethan

: 51-41-2
norepinephrine

Conditions

Conditions	Yield
With hydrogenchloride; hydrogen; palladium on activated charcoal In ethanol for 6h; Ambient temperature;	51.4%

: 138-65-8
Norepinephrine

: 51-41-2
norepinephrine

Conditions

Conditions	Yield
With MANDELIC ACID
With (R)-methoxyphenylacetic acid
With L-Tartaric acid

: 56-40-6
glycine

: 139-85-5
3,4-dihydroxybenzaldehyde

A: 51-41-2
norepinephrine

B: 149-95-1
D-noradrenaline

Conditions

Conditions	Yield
With pyridoxal 5'-phosphate In dimethyl sulfoxide at 20℃; for 89h; Enzymatic reaction; Title compound not separated from byproducts.;

...Expand

: 5090-29-9
1-(3,4-dihydroxyphenyl)-1-oxo-2-amino-ethan-hydrochlorid

: 51-41-2
norepinephrine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 61.4 percent / NaHCO3 / benzene; H2O / 30 h 2: NaBH4 / methanol / 24 h 3: 51.4 percent / H2, conc HCl / Pd/C / ethanol / 6 h / Ambient temperature View Scheme

: 104819-55-8, 104873-27-0, 104873-28-1
R-(+)-2,2'-dinitrobiphenyl-6,6'-dicarbonsaeure-di-N,N'-1-(3,4-dihydroxyphenyl)-1-oxo-2-amido-ethan

: 51-41-2
norepinephrine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH4 / methanol / 24 h 2: 51.4 percent / H2, conc HCl / Pd/C / ethanol / 6 h / Ambient temperature View Scheme

: 60-18-4
L-tyrosine

: 51-41-2
norepinephrine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: tetrahydrobiopterin; oxygen; tyrosine hydroxylase / Enzymatic reaction 2: aromatic L-amino acid decarboxylase / Enzymatic reaction 3: oxygen; dopamine β-hydroxylase; ascorbic acid / Enzymatic reaction View Scheme

: 59-92-7
levodopa

: 51-41-2
norepinephrine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: aromatic L-amino acid decarboxylase / Enzymatic reaction 2: oxygen; dopamine β-hydroxylase; ascorbic acid / Enzymatic reaction View Scheme

: 51-61-6
dopamine

: 51-41-2
norepinephrine

Conditions

Conditions	Yield
With dopamine β-hydroxylase; oxygen; ascorbic acid Enzymatic reaction;

: C14H21N4O3(1+)*Cl(1-)

: 51-41-2
norepinephrine

Conditions

Conditions	Yield
With hydrogenchloride In water at 20℃; for 10h;	6.8 g

: 99-40-1
2-chloro-3',4'-dihydroxyacetophenone

: 51-41-2
norepinephrine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: (R)-α,α-diphenylprolinol; sodium tetrahydroborate; chloro-trimethyl-silane / tetrahydrofuran / 24 h / 10 - 30 °C / Inert atmosphere 2: N,N-dimethyl-formamide / 18 h / 85 °C 3: hydrogenchloride / water / 10 h / 20 °C View Scheme

: C8H9ClO3

: 51-41-2
norepinephrine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 18 h / 85 °C 2: hydrogenchloride / water / 10 h / 20 °C View Scheme

: 138-65-8
Norepinephrine

A: 51-41-2
norepinephrine

B: 149-95-1
D-noradrenaline

Conditions

Conditions	Yield
With phase-transitioned bovine serum albumin film-coated capillary column In methanol pH=8; Resolution of racemate;

: 87-69-4
L-Tartaric acid

: 51-41-2
norepinephrine

: C8H11NO3*C4H6O6*H2O

Conditions

Conditions	Yield
With water In ethanol at 20℃; for 12h;	96.7%

: 50-00-0
formaldehyd

: 51-41-2
norepinephrine

: 41462-32-2
1,2,3,4-tetrahydro-4,6,7-isoquinolinetriol hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride at 24℃; for 24h;	92%

: 51-41-2
norepinephrine

: 130120-90-0
3-<<4-<(tert-butyldimethylsilyl)oxy>phenyl>acetyl>thiazolidine-2-thione

: 130097-10-8
2-[4-(tert-Butyl-dimethyl-silanyloxy)-phenyl]-N-[(R)-2-(3,4-dihydroxy-phenyl)-2-hydroxy-ethyl]-acetamide

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 25℃;	82%

: 51-41-2
norepinephrine

: 74058-64-3
1-(2-Thioxo-thiazolidin-3-yl)-hexadecan-1-one

: 74064-89-4, 94475-55-5
N-hexadecanoyl-L-noradrenaline

Conditions

Conditions	Yield
In tetrahydrofuran; ethanol for 5h; Ambient temperature;	51%

: 122853-43-4
2-(2-methoxyphenoxy)-ethyl methanesulphonate

: 51-41-2
norepinephrine

: 76-05-1
trifluoroacetic acid

: (R)-4-(1-hydroxy-2-((2-(2-methoxyphenoxy)ethyl)amino)ethyl)benzene-1,2-diol trifluoroacetate

Conditions

Conditions	Yield
Stage #1: 2-(2-methoxyphenoxy)-ethyl methanesulphonate; norepinephrine In dimethyl sulfoxide at 70℃; for 6h; Inert atmosphere; Stage #2: trifluoroacetic acid In methanol; water; dimethyl sulfoxide	46%

...Expand

: 51-41-2
norepinephrine

: 3-methoxy-4-(3-phenylpropoxy)phenethyl methanesulfonate

: 76-05-1
trifluoroacetic acid

: (R)-4-(1-hydroxy-2-((3-methoxy-4-(3-phenylpropoxy)phenethyl)amino)ethyl)benzene-1,2-diol trifluoroacetate

Conditions

Conditions	Yield
Stage #1: norepinephrine; 3-methoxy-4-(3-phenylpropoxy)phenethyl methanesulfonate In dimethyl sulfoxide at 70℃; for 6h; Inert atmosphere; Stage #2: trifluoroacetic acid In methanol; water; dimethyl sulfoxide Inert atmosphere;	38%

...Expand

: 16837-38-0
nicotinic anhydride

: 51-41-2
norepinephrine

: N-nicotinoylnorepinephrine

Conditions

Conditions	Yield
In tetrahydrofuran; methanol at 20℃; for 20h;	37%

: 51-41-2
norepinephrine

: 373359-53-6
N-{4-[4-(4-oxopiperidin-1-yl)phenylsulfamoyl]phenyl}acetamide

: N-(4-{[4-(4-{[(2R)-2-(3,4-dihydroxyphenyl)-2-hydroxyethyl]amino}-1-piperidinyl)anilino]sulfonyl}phenyl)acetamide

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol under 258.574 - 1034.3 Torr;	15%

: 51-41-2
norepinephrine

: 84702-73-8
5-azidopentan-2-one

: 186303-33-3
1-(R)-(3.4-dihydroxyphenyl)-2-(1-methyl-4-azidobutylamino)ethanol oxalate salt

Conditions

Conditions	Yield
	15%

: 51-41-2
norepinephrine

: 108-24-7
acetic anhydride

A: 4-[bis-(1H-5,6-diacetoxyindol-2-yl)methyl]-1,2-diacetoxybenzene

B: 67727-64-4
3,4-diacetoxybenzaldehyde

C: 15069-79-1
5,6-diacetoxyindole

D: 1-acetyl-3,5,6-triacetoxyindole

Conditions

Conditions	Yield
Stage #1: norepinephrine With sodium periodate; phosphate buffer In water for 0.0833333h; pH=7.4; Stage #2: acetic anhydride With pyridine	A 7% B 1% C 1% D 3%

...Expand

: 5503-03-7
C18H32O4

: 51-41-2
norepinephrine

: 1036406-97-9
C26H41NO8

Conditions

Conditions	Yield
With oxygen; tris hydrochloride In water; dimethyl sulfoxide at 25℃; for 15h; pH=8.0; regioselective reaction;	6%

: C18H30O3

: 51-41-2
norepinephrine

: 1036407-01-8
C26H39NO7

Conditions

Conditions	Yield
With oxygen; tris hydrochloride In water; dimethyl sulfoxide at 25℃; for 15h; pH=8.0; regioselective reaction;	2%

: 155168-72-2
10-oxo-cis-12-octadecenoic acid

: 51-41-2
norepinephrine

: 1036407-00-7
C26H41NO7

Conditions

Conditions	Yield
With oxygen; tris hydrochloride In water; dimethyl sulfoxide at 25℃; for 15h; pH=8.0;	2%

: 10400-19-8
3-pyridinecarbonyl chloride

: 51-41-2
norepinephrine

: N-nicotinoylnorepinephrine

Conditions

Conditions	Yield
With pyridine

: 51-41-2
norepinephrine

: 26630-36-4
(R)-2-acetylamino-1-(3,4-dimethoxy-phenyl)-ethanol

Conditions

Conditions	Yield
durch Acetylierung und Umsetzung des Reaktionsprodukts mit Diazomethan;

: 51-41-2
norepinephrine

: 490-89-1
noradrenochrome

Conditions

Conditions	Yield
With methanol; silver(l) oxide

: 51-41-2
norepinephrine

: 541-41-3
chloroformic acid ethyl ester

: 99161-02-1, 103565-71-5
((R)-3,4,β-trihydroxy-phenethyl)-carbamic acid ethyl ester

: 51-41-2
norepinephrine

: 108-24-7
acetic anhydride

: 28371-32-6
(R)-2-acetylamino-1-(3,4-diacetoxy-phenyl)-ethanol

: 51-41-2
norepinephrine

: 90-02-8
salicylaldehyde

: 73428-22-5
(R)-N-salicylidenenorepinephrine

Conditions

Conditions	Yield
With ethanol
In methanol

: 51-41-2
norepinephrine

: 83086-06-0
6-oxoheptanoic acid p-methylanilide

: 90900-18-8
6-[(E)-(R)-2-(3,4-Dihydroxy-phenyl)-2-hydroxy-ethylimino]-heptanoic acid p-tolylamide

Conditions

Conditions	Yield
With 3 A molecular sieve In N,N-dimethyl-formamide at 75℃; for 24h;

: 51-41-2
norepinephrine

: 84417-40-3
6-oxo-N-<4-(trifluoromethyl)phenyl>heptanamide

A: 90900-17-7
6-[(E)-(R)-2-(3,4-Dihydroxy-phenyl)-2-hydroxy-ethylimino]-heptanoic acid (4-trifluoromethyl-phenyl)-amide

B: 6-[(R)-2-(3,4-Dihydroxy-phenyl)-2-hydroxy-ethylamino]-hept-6-enoic acid (4-trifluoromethyl-phenyl)-amide

Conditions

Conditions	Yield
With 3 A molecular sieve In N,N-dimethyl-formamide at 75℃; for 24h; Title compound not separated from byproducts;

...Expand

: 51-41-2
norepinephrine

: 130097-16-4
homovanillic acid

: 2-[4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-phenyl]-N-[(R)-2-(3,4-dihydroxy-phenyl)-2-hydroxy-ethyl]-acetamide

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 25℃;

: 51-41-2
norepinephrine

: 75-07-0
acetaldehyde

: 85507-49-9
trans-1,2,3,4-tetrahydro-1-methyl-4,6,7-isoquinolinetriol hydrochloride

: 85507-48-8
cis-1,2,3,4-tetrahydro-1-methyl-4,6,7-isoquinolinetriol hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride for 36h; Product distribution; with formaldehyde, var. pH;
With hydrogenchloride for 36h; Yield given. Yields of byproduct given;

...Expand

: 51-41-2
norepinephrine

: 204763-28-0
4-diethylaminodiazobenzene-4'-isothiocyanate

: 1-[4-(4-Diethylamino-phenylazo)-phenyl]-3-[(R)-2-(3,4-dihydroxy-phenyl)-2-hydroxy-ethyl]-thiourea

Conditions

Conditions	Yield
With acetic acid; triethylamine In acetone Addition; Heating;

: 51-41-2
norepinephrine

A: (R)-3',4'-dihydroxyphenylglycol

B: (R)-3',4'-dihydroxymandelic acid

Conditions

Conditions	Yield
With Krebs solution; monoamine oxidase in lung of rat Kinetics; Further Variations:; Catalysts; Deamination;

: 51-41-2
norepinephrine

: 7732-18-5
water

: 107-15-3
ethylenediamine

air: air

: 28857-14-9
1,2,3,4-tetrahydropyrazino[2,3-g]quinoxaline

Conditions

Conditions	Yield
pH 11;

...Expand

Norepinephrine Specification

The l-Norepinephrine with CAS registry number of 51-41-2 is also known as Noradrenalina. The IUPAC name is 4-[(1R)-2-Amino-1-hydroxyethyl]benzene-1,2-diol. It belongs to product categories of Chiral. Its EINECS registry number is 200-096-6. In addition, the formula is C₈H₁₁NO₃ and the molecular weight is 169.18. This chemical is a off-white to tan solid and should be stored in sealed containers with protection of argon and away from light at the temperature of 4 °C.

Physical properties about l-Norepinephrine are: (1)ACD/LogP: -0.88; (2)# of Rule of 5 Violations: 1 ; (3)#H bond acceptors: 4; (4)#H bond donors: 5; (5)#Freely Rotating Bonds: 6; (6)Index of Refraction: 1.659; (7)Molar Refractivity: 44.63 cm³; (8)Molar Volume: 121 cm³; (9)Surface Tension: 76.7 dyne/cm; (10)Density: 1.397 g/cm³; (11)Flash Point: 221.5 °C; (12)Enthalpy of Vaporization: 73.79 kJ/mol; (13)Boiling Point: 442.6 °C at 760 mmHg; (14)Vapour Pressure: 1.3E-08 mmHg at 25 °C.

Preparation of l-Norepinephrine. The reaction has two steps. Firstly, collar hydroquinone is mixed with chloroacetyl chloride to generate 3,4-dihydroxy-2-chloro acetophenone. Secondly, the reactant reacts with Ammonia or methenamine to obtain the product.

Uses of l-Norepinephrine: it is used to produce 1,2,3,4-tetrahydro-4,6,7-isoquinolinetriol hydrochloride by reaction with formaldehyde. The reaction occurs with reagent 1M HCl at 24 °C for 24 hours. The yield is about 92%. What's more, it is used to as vasoactive drug of anti-shock.

l-Norepinephrine is used to produce 1,2,3,4-tetrahydro-4,6,7-isoquinolinetriol hydrochloride by reaction with formaldehyde.

When you are using this chemical, please be cautious about it. As a chemical, it is very toxic by inhalation, in contact with skin and if swallowed. What's more, it is highly flammable that may cause burns. During using it, wear suitable protective clothing, gloves and eye/face protection. Avoid contact with skin and eyes. Keep away from sources of ignition. After contact with skin, wash immediately. If contact with eyes accidently, rinse immediately with plenty of water and seek medical advice. In case of accident or if you feel unwell seek medical advice immediately.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: C1=CC(=C(C=C1C(CN)O)O)O
2. Isomeric SMILES: C1=CC(=C(C=C1[C@H](CN)O)O)O
3. InChI: InChI=1S/C8H11NO3/c9-4-8(12)5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2/t8-/m0/s1
4. InChIKey: SFLSHLFXELFNJZ-QMMMGPOBSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	6mg/kg (6mg/kg)		Drugs in Japan Vol. 6, Pg. 567, 1982.
mouse	LD50	intravenous	550ug/kg (0.55mg/kg)		Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 226, Pg. 493, 1955.
mouse	LD50	oral	20mg/kg (20mg/kg)		Acta Pharmacologica et Toxicologica. Vol. 31, Pg. 49, 1972.
mouse	LD50	subcutaneous	5mg/kg (5mg/kg)		Naturwissenschaften. Vol. 56, Pg. 615, 1969.
rabbit	LDLo	intravenous	250ug/kg (0.25mg/kg)		Archives Internationales de Pharmacodynamie et de Therapie. Vol. 41, Pg. 365, 1931.
rat	LD50	intravenous	100ug/kg (0.1mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: MUSCLE WEAKNESS LUNGS, THORAX, OR RESPIRATION: DYSPNEA	Journal of Pharmacology and Experimental Therapeutics. Vol. 95, Pg. 502, 1949.

Product Name

Norepinephrine

Synthetic route

Norepinephrine Specification

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