329-56-6

Basic information

• Product Name: L-NORADRENALINE HYDROCHLORIDE
• Synonyms: L-ARTERENOL HYDROCHLORIDE;(-)-ARTERENOL HYDROCHLORIDE;L-NOREPINEPHRINE HYDROCHLORIDE;L-NORADRENALINE HYDROCHLORIDE;aktaminhydrochloride;alpha-(aminomethyl)-3,4-dihydroxy-,hydrochloride,(-)-benzylalcoho;levophedhydrochloride;L-alpha-(aminomethyl)-3,4-dihydroxybenzyl alcohol hydrochloride
• CAS NO: 329-56-6
• Molecular Formula: C₈H₁₁NO₃*ClH
• Molecular Weight: 205.64
• EINECS: 222-395-0
• Mol File: 329-56-6.mol
• Article Data: 2

Chemical Properties

• Melting Point: ~150 °C (dec.)
• Boiling Point: 442.6°Cat760mmHg
• Flash Point: 221.5°C
• Appearance: /
• Density: 1.397g/cm³
• Storage Temp.: 2-8°C
• Solubility: Very soluble in water, slightly soluble in ethanol (96 per cent). It becomes coloured on exposure to air and light.
• CAS DataBase Reference: L-NORADRENALINE HYDROCHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: L-NORADRENALINE HYDROCHLORIDE(329-56-6)
• EPA Substance Registry System: L-NORADRENALINE HYDROCHLORIDE(329-56-6)

Safety Data

• Hazard Codes: T,C,F
• Statements: 25-34-11
• Safety Statements: 45-36/37/39-26-16
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: DN6475000
• F: 3-8-10-23
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 329-56-6(Hazardous Substances Data)

Usage

Chemical Properties

White or brownish-white, crystalline powder.

Uses

Alpha-adrenoceptor agonist.

Safety Profile

Poison by ingestion,subcutaneous, and intraduodenal routes. When heated todecomposition it emits very toxic fumes of HCl and NOx.

Purification Methods

Recrystallise arterenol from isoPrOH and store it in the dark as it is oxidised under light (see preceding entry). [Tullar J Am Chem Soc 70 2067 1948, Beilstein 13 III 2382.]

InChI:InChI=1/C8H11NO3.ClH/c9-4-8(12)5-1-2-6(10)7(11)3-5;/h1-3,8,10-12H,4,9H2;1H/t8-;/m1./s1

Synthetic route

C44H36N4O12P2(2-)*C8H11NO3*H(1+) → norepinephrine hydrochloride (329-56-6) + C44H36N4O12P2(2-)

Conditions	Yield
In d(4)-methanol; water-d2 Equilibrium constant;

N-{{7-[bis(carboxymethyl)amino]coumarin-4-yl}methyloxycarbonyl}-L-norepinephrine (1031721-23-9) → 7-[bis(carboxymethyl)amino]-4-(hydroxymethyl)coumarin (876275-37-5) + carbon dioxide (124-38-9) + norepinephrine hydrochloride (329-56-6)

Conditions	Yield
With potassium hydroxide; HEPES buffer In acetonitrile pH=7.2; Quantum yield; UV-irradiation;

norepinephrine hydrochloride (329-56-6) + 4-amino-3,6-disulfo-1,8-naphthaldehyde anhydride dipotassium salt (79539-35-8) → C20H14N2O11S2(2-)*2K(1+)

Conditions	Yield
In water Heating; pH 5, Li(1+)/H(1+) acetate buffer;

L-Cysteine (52-90-4) + norepinephrine hydrochloride (329-56-6) → 7-(1-Hydroxy-2-aminoethyl)-3,4-dihydro-5-hydroxy-2H-1,4-benzothiazine-3-carboxylic acid (175482-45-8) + (R)-8-((R)-2-Amino-1-hydroxy-ethyl)-5-hydroxy-3,4-dihydro-2H-benzo[1,4]thiazine-3-carboxylic acid + (R)-6-((R)-2-Amino-2-carboxy-ethylsulfanyl)-7-((R)-2-amino-1-hydroxy-ethyl)-5-hydroxy-3,4-dihydro-2H-benzo[1,4]thiazine-3-carboxylic acid + (R)-2-Amino-3-[4-((R)-2-amino-2-carboxy-ethylsulfanyl)-6-((R)-2-amino-1-hydroxy-ethyl)-2,3-dihydroxy-phenylsulfanyl]-propionic acid

Conditions	Yield
With phosphate buffer for 0.5h; electro-oxidation reaction; Further byproducts given;

L-Cysteine (52-90-4) + norepinephrine hydrochloride (329-56-6) → 7-(1-Hydroxy-2-aminoethyl)-3,4-dihydro-5-hydroxy-2H-1,4-benzothiazine-3-carboxylic acid (175482-45-8) + (R)-8-((R)-2-Amino-1-hydroxy-ethyl)-5-hydroxy-3,4-dihydro-2H-benzo[1,4]thiazine-3-carboxylic acid + (R)-2-Amino-3-[4-((R)-2-amino-2-carboxy-ethylsulfanyl)-6-((R)-2-amino-1-hydroxy-ethyl)-2,3-dihydroxy-phenylsulfanyl]-propionic acid + (R)-6-((R)-2-Amino-2-carboxy-ethylsulfanyl)-8-((R)-2-amino-1-hydroxy-ethyl)-5-hydroxy-3,4-dihydro-2H-benzo[1,4]thiazine-3-carboxylic acid

Conditions	Yield
With phosphate buffer for 0.5h; electro-oxidation reaction; Further byproducts given;

L-Cysteine (52-90-4) + norepinephrine hydrochloride (329-56-6) → 7-(1-Hydroxy-2-aminoethyl)-3,4-dihydro-5-hydroxy-2H-1,4-benzothiazine-3-carboxylic acid (175482-45-8) + (R)-8-((R)-2-Amino-1-hydroxy-ethyl)-5-hydroxy-3,4-dihydro-2H-benzo[1,4]thiazine-3-carboxylic acid + (R)-2-Amino-3-[4-((R)-2-amino-2-carboxy-ethylsulfanyl)-6-((R)-2-amino-1-hydroxy-ethyl)-2,3-dihydroxy-phenylsulfanyl]-propionic acid + (R)-6,7-Bis-((R)-2-amino-2-carboxy-ethylsulfanyl)-8-((R)-2-amino-1-hydroxy-ethyl)-5-hydroxy-3,4-dihydro-2H-benzo[1,4]thiazine-3-carboxylic acid

Conditions	Yield
With phosphate buffer for 0.5h; electro-oxidation reaction; Further byproducts given;

norepinephrine hydrochloride (329-56-6) → 4-((R)-2-Amino-1-hydroxy-ethyl)-[1,2]benzoquinone; hydrochloride

Conditions	Yield
With hydrogenchloride for 0.5h; electrochemical oxidation;

L-Cysteine (52-90-4) + norepinephrine hydrochloride (329-56-6) → (R)-6,8-Bis-((R)-2-amino-2-carboxy-ethylsulfanyl)-5-hydroxy-3,4-dihydro-2H-benzo[1,4]thiazine-3-carboxylic acid + (R)-6,7,8-Tris-((R)-2-amino-2-carboxy-ethylsulfanyl)-5-hydroxy-3,4-dihydro-2H-benzo[1,4]thiazine-3-carboxylic acid + (R)-7-[(R)-2-((R)-2-Amino-2-carboxy-ethyldisulfanyl)-1-carboxy-ethylamino]-10-((R)-2-amino-2-carboxy-ethylsulfanyl)-9-hydroxy-1,2,3,6-tetrahydro-4,5-dithia-1,8-diaza-phenanthrene-2-carboxylic acid (196309-90-7)

Conditions	Yield
pH 7.4;

norepinephrine hydrochloride (329-56-6) + C44H36N4O12P2(2-) → C44H36N4O12P2(2-)*C8H11NO3*H(1+)

Conditions	Yield
In d(4)-methanol; water-d2 Equilibrium constant; Thermodynamic data;

norepinephrine hydrochloride (329-56-6) → 2-S-Cysteinylepinephrine

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.1M aq. HCl / 0.5 h / electrochemical oxidation 2: 0.1N HCl View Scheme

norepinephrine hydrochloride (329-56-6) → 5-S-Cysteinylepinephrine (115331-10-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: 0.1M aq. HCl / 0.5 h / electrochemical oxidation 2: 0.1N HCl View Scheme

3-(1,6-dihydro-6-oxo-9H-purin-9-yl)-propanoic acid,4-nitrophenyl ester + norepinephrine hydrochloride (329-56-6) → AIT-297

Conditions	Yield
With triethylamine In chloroform; dimethyl sulfoxide	110%

C29H32N2O11 (937021-61-9) + norepinephrine hydrochloride (329-56-6) → N-{{7-[bis(tert-butoxycarbonylmethyl)amino]coumarin-4-yl}methyloxycarbonyl}-L-norepinephrine (1031721-30-8)

Conditions	Yield
With dmap In N,N-dimethyl-formamide at 20℃; for 3.5h;	70 mg

C36H30O18(6-)*6Na(1+) + norepinephrine hydrochloride (329-56-6) → C8H11NO3*C36H30O18(6-)*ClH*6Na(1+)

Conditions	Yield
In water-d2 at 24.84℃; pH=7.1; aq. phosphate buffer;

5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrakis[N-(6′-(2-((2-hydroxypropanoyl)oxy)propanamido)hexyl)carbamoylmethoxy]-2,8,14,20-tetrathiacalix[4]arene + norepinephrine hydrochloride (329-56-6) → C8H11NO3*C96H144N8O24S4*H(1+)

Conditions	Yield
In methanol

Upstream product

• 1031721-23-9 N-{{7-[bis(carboxymethyl)amino]coumarin-4-yl}methyloxycarbonyl}-L-norepinephrine 

Downstream Products

• 175482-45-8 7-(1-Hydroxy-2-aminoethyl)-3,4-dihydro-5-hydroxy-2H-1,4-benzothiazine-3-carboxylic acid 
• 115331-10-7 5-S-Cysteinylepinephrine 

Relevant articles and documents

{7-[Bis(carboxymethyl)amino]coumarin-4-yl}methoxycarbonyl derivatives for photorelease of carboxylic acids, alcohols/phenols, thioalcohols/thiophenols, and amines

Light-induced release of biomolecules from inactive precursor molecules represents a powerful method to study cellular processes with high temporal and spatial resolution. Here we report the synthesis and photochemistry of a series of {7-[bis(carboxymethyl)amino]coumarin-4-yl}methyl carboxylates, carbonates, carbamates, and thiocarbonates as potential phototriggers for compounds with COOH, OH, NH2, and SH functions. The compounds are soluble in aqueous buffer, show low fluorescence, and are efficiently photolysed by irradiation with UV/Vis or IR light to release carboxylates, alcohols, phenols, amines, thioalcohols, or thiophenols.