90-82-4 Usage
Description
Pseudoephedrine is a naturally occurring stereoisomer of ephedrine, belonging to the sympathomimetic drug class. It is found in plants of the genus Ephedra and is known for its mixed-acting decongestant properties, activating both αand β-adrenergic receptors directly by binding to the receptor itself and indirectly by causing norepinephrine release in synaptic nerve terminals. Pseudoephedrine is also used as a precursor in the synthesis of methamphetamine, leading to stringent regulations on its sale in some countries.
Used in Pharmaceutical Industry:
Pseudoephedrine is used as a nasal decongestant for the treatment of nasal congestion. It acts by directly stimulating α-adrenergic receptors in the respiratory tract mucosa, causing vasoconstriction and resulting in the shrinkage of swollen nasal mucous membranes, reduction of tissue hyperemia, edema, and nasal congestion, as well as an increase in nasal airway patency. Additionally, it may increase the drainage of sinus secretions and open obstructed eustachian ostia. Pseudoephedrine may also cause relaxation of bronchial smooth muscle by stimulating β-adrenergic receptors.
Used in Research and Forensic Applications:
Pseudoephedrine is used as an analytical reference standard, categorized as an amphetamine. It is particularly relevant in research and forensic applications due to its role as a precursor in the synthesis of methamphetamine.
Chemical Properties:
Pseudoephedrine is characterized by its white crystal appearance.
Environmental Fate
Through use as a decongestant and production, release to
the environment may result from various waste streams. Pseudoephedrine is also found in plants in the genus Ephedra
(Ephedraceae) otherwise known as Ma Huang. It has a vapor
pressure of 8.3×104 mm Hg at 25 °C and if released into air
it will exist both as vapor and in particulate phase in the
atmosphere. Vapor-phase pseudoephedrine will be degraded
by reactions with hydroxyl radicals, which are photochemically
produced. The half-life for this reaction is estimated at 4 h.
Particulate-phase pseudoephedrine will be removed from the
atmosphere by wet and dry deposition. Pseudoephedrine is not
susceptible to direct photolysis by sunlight.
Based upon an estimated Koc of 73, pseudoephedrine is
expected to have a high mobility in soil. The pKa of 10.25
indicates that it will exist primarily in the cation form in the
environment and it will absorb more strongly to soil containing
clay or organic carbon.
Purification Methods
Crystallise the amine from dry diethyl ether, or from water and dry it in a vacuum desiccator. [Beilstein 13 IV 1878.]
Toxicity evaluation
Pseudoephedrine is a weak base (pKa, 9.4) that stimulates both
α- and β-adrenergic receptors, as well as causing the release of
neuronal norepinephrine. This mixed α/β adrenergic stimulation
produces both hypertension and tachycardia, as opposed
to the hypertension with reflex bradycardia seen with selective
a agonists.
Check Digit Verification of cas no
The CAS Registry Mumber 90-82-4 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 9 and 0 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 90-82:
(4*9)+(3*0)+(2*8)+(1*2)=54
54 % 10 = 4
So 90-82-4 is a valid CAS Registry Number.
InChI:InChI=1/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10+/m0/s1
90-82-4Relevant articles and documents
Peroxygenase-Catalysed Epoxidation of Styrene Derivatives in Neat Reaction Media
Alcalde, Miguel,Arends, Isabel W. C. E.,Hollmann, Frank,Paul, Caroline E.,Rauch, Marine C. R.,Tieves, Florian
, (2019/08/30)
Biocatalytic oxyfunctionalisation reactions are traditionally conducted in aqueous media limiting their production yield. Here we report the application of a peroxygenase in neat reaction conditions reaching product concentrations of up to 360 mM.
Unlocking the potential of phenacyl protecting groups: CO2-based formation and photocatalytic release of caged amines
Speckmeier, Elisabeth,Klimkait, Michael,Zeitler, Kirsten
, p. 3738 - 3745 (2018/04/14)
Orthogonal protection and deprotection of amines remain important tools in synthetic design as well as in chemical biology and material research applications. A robust, highly efficient, and sustainable method for the formation of phenacyl-based carbamate esters was developed using CO2 for the in situ preparation of the intermediate carbamates. Our mild and broadly applicable protocol allows for the formation of phenacyl urethanes of anilines, primary amines, including amino acids, and secondary amines in high to excellent yields. Moreover, we demonstrate the utility by a mild and convenient photocatalytic deprotection protocol using visible light. A key feature of the [Ru(bpy)3](PF6)2-catalyzed method is the use of ascorbic acid as reductive quencher in a neutral, buffered, two-phase acetonitrile/water mixture, granting fast and highly selective deprotection for all presented examples.
POLYMORPHIC AND AMORPHOUS FORMS OF (R)-2-HYDROXY-2-METHYL-4-(2,4,5-TRIMETHYL-3,6-DIOXOCYCLOHEXA-1,4-DIENYL)BUTANAMIDE
-
Paragraph 0188, (2016/07/05)
Disclosed herein are polymorphic and amorphous forms of anhydrate, hydrate, and solvates of (R)-2-hydroxy-2-methyl-4-(2,4,5-trimethyl-3,6-dioxocyclohexa-1,4-dienyl)butanamide and methods of using such compositions for treating or suppressing oxidative stress disorders, including mitochondrial disorders, impaired energy processing disorders, neurodegenerative diseases and diseases of aging. Further disclosed are methods of making such polymorphic and amorphous forms.
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