51-41-2 Usage
Chemical Properties
solid
Uses
Different sources of media describe the Uses of 51-41-2 differently. You can refer to the following data:
1. Vascular active drug resistance to shock
2. An adrenergic neurotransmitter.
3. Norepinephrine is used for increasing cardiac constriction and for the necessary elevation of blood pressure after sharp decline, which can result from surgical intervention or
trauma.
Definition
ChEBI: The R-enantiomer of noradrenaline.
Brand name
Levophed (Hospira);Noradrec;Xylotox.
World Health Organization (WHO)
Vasoconstrictor agents have been in use for many years to
prolong duration of action of local anaesthetics, particularly in dentistry.
Combination products containing epinephrine or levarterenol in concentrations of
1:80,000 or less remain widely available. See also WHO comment for epinephrine.
Biological Functions
Most central noradrenergic neurons are located in the
nucleus locus ceruleus of the pons and in neurons of
the reticular formation. Fibers from these nuclei innervate
a large number of cortical, subcortical, and spinomedullary
fields. Many functions have been ascribed to
the central noradrenergic neurons, including a role in affective disorders (see Chapter 33), in learning and
memory, and in sleep–wake cycle regulation.The mammalian
CNS contains both α- and β-adrenoceptors.
General Description
Norepinephrine (NE, Levophed) differs from DA onlyby addition of a 1-OH substituent (β-OH-DA) and from Eonly by lacking the N-methyl group. Like DA, it is polar andrapidly metabolized by both COMT and MAO, resulting inpoor oral bioavailability and short DOA (1 or 2 minutes evenwhen given intravenously). It is a stimulant of α1-, α2-, andβ1-adrenoceptors (notice that lacking the N-methyl group resultsin lacking β2- and β3-activity). It is used to counteractvarious hypotensive crises, because its α-activity raisesblood pressure and as an adjunct treatment in cardiac arrestbecause its β-activity stimulates the heart. It has limitedclinical application caused by the nonselective nature of itsactivities.
Hazard
May cause local tissue necrosis, headache,
bradycardia, hypertension; poison; teratogen; mutagen.
Pharmacology
Norepinephrine is the primary neurotransmitter produced and released by adrenergic neurons, and in literature it is also described as and called () noradrenaline or levarterenol.
This vasopressor catecholamine reduces both the resistance and capacity of blood vessels
by stimulating α-adrenoreceptors and having a direct cardiostimulatory effect, which is
accomplished by activation of β1-adrenoreceptors. Norepinephrine exhibits significantly
less activity than epinephrine as a drug for widening blood vessels through the activation
of β2-adrenoreceptors. Elevation of both stylistic and diastolic blood pressure is a typical
reaction to intravenous introduction of norepinephrine.
Safety Profile
Poison by ingestion,
intraperitoneal, subcutaneous, and
intravenous routes. An experimental
teratogen. Experimental reproductive
effects. Human mutation data reported. A
sympathomimetic vasopressor. When heated
to decomposition it emits toxic fumes of
NOx.
Synthesis
Norepinephrine, L-1-(3,4-dihydroxyphenyl)-2-aminoethanol (11.1.4), is synthesized by two methods starting from 3,4-dihydroxybenzaldehyde. According to the first method, the indicated aldehyde is transformed into the cyanohydrin (11.1.3) by reaction with hydrogen cyanide, which is then reduced into norepinephrine (11.1.5).
The second method consists of the condensation of diacetate of the same aldehyde with nitromethane, which forms (3,4-diacetoxyphenyl)-2-nitroethanol (11.1.5). Then the nitro group is reduced and the product (11.1.6) is hydrolyzed into the desired norepinephrine (11.1.4) [4,9,13,14].
Purification Methods
Recrystallise adrenor from EtOH and store it in the dark under N2. [pKa, Lewis Brit J Pharmacol Chemother 9 488 1954, UV: Bergstr.m et al. Acta Physiol Scand 20 101 1950, Fluorescence: Bowman et al. Science NY 122 32 1955, Tullar J Am Chem Soc 70 2067 1948.] The L-tartrate salt monohydrate has m 102-104.5o, [] D -11o (c 1.6, H2O), after recrystallisation from H2O or EtOH. [Beilstein 13 III 2382.]
Check Digit Verification of cas no
The CAS Registry Mumber 51-41-2 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 1 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 51-41:
(4*5)+(3*1)+(2*4)+(1*1)=32
32 % 10 = 2
So 51-41-2 is a valid CAS Registry Number.
InChI:InChI=1/C8H11NO3/c9-8(12)4-5-1-2-6(10)7(11)3-5/h1-3,8,10-12H,4,9H2
51-41-2Relevant articles and documents
In-situ and one-step preparation of protein film in capillary column for open tubular capillary electrochromatography enantioseparation
Li, Ling,Xue, Xuqi,Zhang, Huige,Lv, Wenjuan,Qi, Shengda,Du, Hongying,Manyande, Anne,Chen, Hongli
supporting information, p. 2139 - 2142 (2021/04/07)
In this work, the phase-transitioned BSA (PTB) film using the mild and fast fabrication process adhered to the capillary inner wall uniformly, and the fabricated PTB film-coated capillary column was applied to realize open tubular capillary electrochromatography (OT-CEC) enantioseparation. The enantioseparation ability of PTB film-coated capillary was evaluated with eight pairs of chiral analytes including drugs and neurotransmitters, all achieving good resolution and symmetrical peak shape. For three consecutive runs, the relative standard deviations (RSD) of migration time for intra-day, inter-day, and column-to-column repeatability were in the range of 0.3%–3.5%, 0.2%–4.9% and 2.1%–7.7%, respectively. Moreover, the PTB film-coated capillary column ran continuously over 300 times with high separation efficiency. Therefore, the coating method based on BSA self-assembly supramolecular film can be extended to the preparation of other proteinaceous capillary columns.
Method for synthesizing noradrenaline
-
Paragraph 0037; 0045; 0046; 0049; 0052; 0057; 0062, (2018/06/04)
The invention discloses a method for synthesizing noradrenaline. The method comprises the steps that (-)-diisopinocampheyl chloroborane serves as a catalyst, a reducing agent is utilized in an ether solvent at a low temperature, particularly (-)-diisopinocampheyl chloroborane directly reduces noradrenaline to generate levarterenol, and a solution containing noradrenaline is obtained. According tothe method, levarterenol can be directly obtained by using (-)-diisopinocampheyl chloroborane as the reducing agent, resolution is not needed, and the cost and potential safety hazards are reduced simultaneously.
Synthesis of aromatic 1,2-amino alcohols utilizing a bienzymatic dynamic kinetic asymmetric transformation
Steinreiber, Johannes,Schuermann, Martin,Van Assema, Friso,Wolberg, Michael,Fesko, Kateryna,Reisinger, Christoph,Mink, Daniel,Griengl, Herfried
, p. 1379 - 1386 (2008/04/03)
The applicability of the recent published bienzymatic protocol for the synthesis of (R)-2-amino-1-phenylethanol was tested using L-threonine aldolase from Pseudomonas putida and L-tyrosine decarboxylase from either Enterococcus faecalis (Efa) or two genes from Enterococcus faecium (Efil, Efi2). In all 21 benzaldehyde derivatives were applied for an initial TLC screening. On a small scale, octopamine and noradrenaline were obtained as (S)-enantiomers using Efil. Three protocols were upscaled yielding enantioenriched (S)-octopamine (yield 99%, ee 81%), (R)-2-amino-1-phenylethanol (yield 61%, ee 62%) and (S)-noradrenaline (yield 76%, ee 79%).
