14838-15-4 Usage
Description
Phenylpropanolamine (PPA) is a mixed-acting sympathomimetic
amine similar to ephedrine. Its primary mechanism of
action is through direct a-adrenergic agonism, but there is also
indirect stimulation of norepinephrine release. In November
2000, the US Food and Drug Administration (FDA) Nonprescription
Drugs Advisory Committee determined that there is
a significant association between PPA and hemorrhagic stroke
and recommended that PPA not be considered safe for over-thecounter
use. At this time, a letter was issued to manufacturers
requesting voluntary removal of PPA from their products. Later,
in 2005, the FDA published a Tentative Final Monograph for
PPA-containing products proposing Category II status (not
generally recognized as safe and effective). To date, no Final
Monograph has been released; however, all manufacturers have
removed PPA from their products.
Uses
Different sources of media describe the Uses of 14838-15-4 differently. You can refer to the following data:
1. Norephedrine, also called Phenylpropanolamine (PPA), is a synthetic form of the ephedrine alkaloid. Used in treatment of urinary incontinence in dogs and cats; decongestant nasal. After reports of the occurrence of intracranial hemorrhage and other adverse effects, including several deaths, PPA is no longer sold in USA and Canada.
2. The central nervous excitement
3. PPA was used as a nasal decongestant and as an anorectic.
Studies have shown benefit in humans for urinary incontinence,
and PPA is still used in veterinary medicine for this purpose.
Brand name
A.g.multix;Acutrim;Adistop-f;Amertuss;Amplisiex;Am-tuss liq;Anorexin;Antiadipositum;Apoephedrin;e
Aridose;Arm;Bifed-20;Biphetane;Biphetap;Blu-hist;Brocon cr;Bromanate;Bromepaph;Brometapp;Bronco-quintoxil;Cenadex;Chlor-rest;Cinturex;Cletanol;Codimal;Cofpac;Cold cap;Coldecon;Col-decon;Conex-grippe;Contop;Coricidin f;Corsym;Coryztime;Cremacoat;Dalca;Decidex;Decomine;Demazine;Deprecstop;Dexatrim;D-sinus;Efed ii;Eficol;Endal;Endecon;Endex;E-son;Espornade spansule;E-tapp 3;Exyphen;Factus;Fornagest;Fugoa n;Gardax;Ginsopan;Headway;Histade;Histatapp;Hsp 540;Ipercron;Kol-tac;Kontexin;Koryza;Leder;Lipo-sinahist;Lunerin;Mardram;Minus-x;Monatuss;Mucolyt-expecto;Nd-hist;Nectatussin;Neosoldana;Nexaam;Nobese;Norephedrine;Nornatane;Ornacol;Ornatos;Ornex;Pabron nose;Panacorn;Panadyl;Parhist;Partapp;Pholcolix spansule;Pneumidex;Polcimut;Profenade;Propagest;Reduzin;Rhindecon;Rhinergal;Rhinervert;Rhinicept;Rhinidrin;Rhinocap;Rinexin;Rinomar;Rinotussal;Rinurel lictus;Rinurel tablets;Rinutan;Rotabromophen;Rupton;Rynatapp;Rynex;Ryza-gesic;Sacietyl;Scotuss;Secron;Sinacin;Sinudan;Sinu-lets;Sinutab cough l;Spandecon;Srda;Sto-caps;Sulfa-probocon;Symptrol;Taviset;Tinaroc;Totolin;Tricon;Tri-congestic;Triogesic elixir;Triominic;Triotussic;Turbispan;Tussilene-dm;V cold;Veltane;Veltap;Vernate;Vistaminic;Voxin-pg;W 58;X 112 antiadipo;Zerinol;Partuss;Permatrim;Phenapap.
World Health Organization (WHO)
Phenylpropanolamine, a symopathomimetic amine, has been
widely available in over-the-counter preparations since 1941. It is one of the most
frequently used nasal decongestants and it is a common ingredient in preparations
for weight reduction, although doubts have been raised about its usefulness in this
indication. It is also used in stress incontinence. Its use has been associated with
occasional excessive elevation of blood pressure, especially in hypersensitive
individuals.
General Description
Phenylpropanolamine is the N-desmethylanalog of ephedrine and thus has many similar properties.Lacking the N-methyl group, phenylpropanolamine is slightlymore polar, and therefore does not enter the CNS as well asephedrine. This modification gives an agent that has slightlyhigher vasopressive action and lower central stimulatoryaction than ephedrine. Its action as a nasal decongestant ismore prolonged than that of ephedrine. It is orally active.Phenylpropanolamine was a common active component inOTC appetite suppressants and cough and cold medicationsuntil 2001 when the Food and Drug Administration (FDA)recommended its removal from such medications, becausestudies showed an increased risk of hemorrhagic stroke inyoung women who took the drug.
Safety Profile
Moderately toxic by subcutaneousroute. When heated to decomposition it emits very toxicfumes of NOx.
Toxicity evaluation
The primary action of PPA is direct a-adrenergic agonism,
though it also causes indirect release of norepinephrine at
postganglionic sympathetic nerve terminals. PPA also has
weak β agonistic properties. Hypertension results from α adrenergic
mediated vasoconstriction of peripheral blood
vessels. Reflex bradycardia is common. Sympathomimetic
effects can produce anxiety, insomnia, agitation, tremor,
tachycardia, and mydriasis.
Check Digit Verification of cas no
The CAS Registry Mumber 14838-15-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,8,3 and 8 respectively; the second part has 2 digits, 1 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 14838-15:
(7*1)+(6*4)+(5*8)+(4*3)+(3*8)+(2*1)+(1*5)=114
114 % 10 = 4
So 14838-15-4 is a valid CAS Registry Number.
14838-15-4Relevant articles and documents
A modular, low footprint and scalable flow platform for the expedient α-aminohydroxylation of enolizable ketones
Kassin, Victor-Emmanuel H.,Morodo, Romain,Toupy, Thomas,Jacquemin, Isaline,Van Hecke, Kristof,Robiette, Rapha?l,Monbaliu, Jean-Christophe M.
, p. 2336 - 2351 (2021/04/07)
The unique reactivity profile of α-chloronitroso derivatives is expressed to its fullest potential through the development of an integrated, modular and scalable continuous flow process for the electrophilic α-aminohydroxylation of various enolizable ketones. Flow conditions contribute to mitigating the high reactivity and toxicity of α-chloronitroso derivatives and provide an efficient, versatile and safe protocol for the α-aminohydroxylation of ketones with a minimal footprint. Fundamental aspects of the α-aminohydroxylation process were computed by DFT and further supported the experimental observations, hence leading to the unprecedented α-chloronitroso-based α-aminohydroxylation of primary, secondary and tertiary substrates. Recycling of the carbon backbone of the α-chloronitroso derivatives provides a high atom economy for the preparation of value-added molecules. This work showcases α-chloronitroso derivatives as economic and efficient vehicles for transferring electrophilic synthons of hydroxylamine toward nucleophilic enolates. A representative range of precursors and analogs of pharmaceutical active ingredients, including WHO essentials and drugs in shortage (such as epinephrine and ketamine), are prepared within minutes according to a fully concatenated process. The process features sequential modules with distinct unit operations including chemical transformations and multiple in-line extractions. The process relies on an upstream chemical Generator that manages the preparation of α-chloronitroso derivatives and that feeds downstream a series of α-aminohydroxylation modules. The setup is amenable to the addition of libraries of compounds for feeding upstream the process of discovery in medicinal chemistry and is transposable to pilot scale. Several layers of in-line analytical procedures are featured to improve process control and safety.
Chiral-Organotin-Catalyzed Kinetic Resolution of Vicinal Amino Alcohols
Yang, Hui,Zheng, Wen-Hua
supporting information, p. 16177 - 16180 (2019/11/03)
A highly efficient kinetic resolution of racemic amino alcohols has been achieved for the first time with a chiral tin catalyst. A chiral organotin compound with 3,4,5-trifluorophenyl groups at the 3,3′-positions of the binaphthyl framework enabled this transformation with excellent yield and high enantioselectivity. The process tolerates aryl- and alkyl-substituted amino alcohols and a variety of other substrates, affording the corresponding products in high enantioselectivity and with s factors up to >500.
Charge-transfer interactions: An efficient tool for recycling bis(oxazoline)-copper complexes in asymmetric henry reactions
Didier, Dorian,Magnier-Bouvier, Caroline,Schulz, Emmanuelle
supporting information; experimental part, p. 1087 - 1095 (2011/07/09)
An anthracenyl-modified chiral bis(oxazoline) copper complex has been demonstrated to efficiently promote nitroaldol reactions between structurally varying aldehydes and nitromethane or nitroethane. The catalyst was recovered through formation of a charge transfer complex between the chiral ligand and trinitrofluorenone and its subsequent precipitation with pentane. The efficiency of this procedure was proved through several consecutive catalytic cycles that allowed the sturdy formation of the expected product with a high enantioselectivity. The catalyst′s stability was also put to the test in an original multi-substrate procedure. Following the same recovery concept, a new heterogeneous procedure was tested for which trinitrofluorenone was covalently linked to a silica support. Asymmetric heterogeneous catalysis was performed under these conditions as one of the few examples demonstrating the potential catalyst recycling in nitroaldol reactions through reversible, non-covalent interactions. Copyright
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