The post PSEUDOEPHEDRINE Synthesis, SAR, MCQ,Structure,Chemical Properties and Therapeutic Uses appeared first on Gpatindia: Pharmacy Jobs, Admissions, Scholarships, Conference,Grants, Exam Alerts.
]]>(S,S)-2-methylamino-1-phenylpropan-1-ol.
Pseudoephedrine is an indirect acting sympathomimetic amine drug.
S. NO. | PHYSICAL AND CHEMICAL PROPERTIES | |
1 | Molecular weight | 165.23 g/mol |
2 | Physical appearance | Present in solid form; crystals from ether. |
3 | Melting point | 119°C |
4 | Solubility | Sparingly soluble in water;freely soluble in alcohol and ether; very soluble in benzene |
5 | Octanol/water partition coefficient | 0.89 |
6 | Presence of ring | Benzene ring |
7 | Number of chiral centers | 2 |
i. Pseudoephedrine produces agonism of α-adrenergic recepetors and less strongly to the ß-adrenergic receptors.
ii. This produces vasoconstriction.
iii. Further, pseudoephedrine also inhibits norepinephrine, dopamine, serotonin transportors, NF-kappa-B, NFAT and AP-1. [1]
The SAR of Adrenergic agonist can be discussed as follows:
R1 substitution:
R2 substitution:
R3 substitution on the aromatic ring:
If phenyl group has no phenolic substituent then it may act directly or indirectly. [2]
i. Yeast strains like Candida utilis or Saccharomyces cerevisiae are added to the mixture of water, dextrose and pyruvate decarboxylase.
ii. Benzaldehyde is added to the vats afterwards.
iii. Yeast converts Dextrose into L-phenylacetylcarbinol
iv. Pseudoehedrine is produced from L-phenylacetylcarbinol via reductive amination.
Pseudophedrine is used:
Side effects of pseudoephedrine are:
Q.1 What can be the correct IUPAC nomenclature of Pseudoephedrine?
a) (±)-1-cyclohexyl-N-methylpropan-2-amine
b) 4-(2-aminopropyl)phenol
c) (S,S)-2-methylamino-1-phenylpropan-1-ol.
d) 3-[(1R,2S)-2-amino-1-hydroxypropyl]phenol
Q.2 Which amongst the following statements is/are incorrect related to the SAR of Pseudoephedrine?
I. Primary or secondary aliphatic amine separated by two carbons from a substituted benzene ring is essential for the high agonist activity.
II. The hydroxyl substituted carbon must be in the R configuration for the maximal direct activity.
a) I
b) II
c) I, II
d) None
Q.3 The correct order for the synthesis of drug pseudoephedrine from dextrose can be?
I. Conversion to L-phenylacetylcarbinol by yeast.
II. Reductive amination
III. Addition of benzaldehyde
a) II – I – III
b) I – II – III
c) III – I – II
d) I – II – III
Q.4 Side effect of drug pseudoephedrine is?
a) Anxiety
b) Baldness
c) Increased blood calcium level
d) Decrease in blood count
Q.5 Match the following drugs with correct molecular weights-
i. Pseudoephedrine | A. 155.28 gm/mol |
ii. Hydroxyamphetamine | B. 165.23 gm/mol |
iii. Metaraminol | C. 151.21 gm/mol |
iv. Propylhexedrine | D. 167.2 gm/mol |
a) i-B, ii-C, iii-D, iv-A
b) i-D, ii-A, iii-B, iv-C
c) i-C, ii-B, iii-A, iv-D
d) i-A, ii-D, iii-C, iv-B
Q.6 An example of drug from class “Mixed Acting Sympathomimetics” is?
a) Dobutamine
b) Ritodrine
c) Epinephrine
d) Pseudoephedrine
Q.7 The type of ring system found in Pseudoephedrine is?
a) Purine ring system
b) Pyrimidine ring system
c) Benzene
d) No ring present
1-c
2-d
3-c
4-a
5-a
6-d
7-c
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