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]]>(R)-3-[-1-hydroxy-2-(methylamino)ethyl]phenol.
Phenylephrine is a selective α1-adrenergic agonist. [1]
S. NO. | PHYSICAL AND CHEMICAL PROPERTIES | |
1 | Molecular weight | 162.2 g/mol |
2 | Physical appearance | Present in solid form |
3 | Melting point | 169-172°C |
4 | Solubility | Freely soluble in water |
5 | Presence of ring | Benzene ring |
6 | Number of chiral centers | 1 |
R1 substitution:
R2 substitution:
R3 substitution on the aromatic ring:
i. 3-(benzyloxy)benzaldehyde reacts with ethylbromoacetate to give ethyl3-(3-(benzyloxy)phenyl)-3-hydroxypropanoate.
ii. The latter compound undergoes nitration to give an intermediatecompound which gives oxazolidone later.
iii. The compound is then reacted with sodium hydride in presence of methyliodide to give 5-(3-(benzyloxy)phenyl)-3-methyloxazolidin-2-one which on reduction gives phenylephrine.
The drug used for the treatment of:
It is also used as a decongestatnt, for the dilation of pupil and during anasthetics.
Side effects of phenylephrine include hypertension, prostatic hyperplasia, hyperemia, seizures, upset stomach, abdominal cramping, vomiting issues.
Extended use of the drug causes rhinitis medicamentosa.
Q.1 Which term is NOT associated with the drug phenylephrine?
a) DROSYN
b) N-COOL
c) PENREX
d) FLUDARA
Q.2 Melting point of Phenyephrine is?
a) 169-172 °C
b) 110-112 °C
c) 234-237 °C
d) 201-204 °C
Q.3 The drug phenylephrine shows its action through
a) Functioning as α1-adrenergic agonist
b) Functioning as ß-adrenergic agonist
c) Both a) and b)
d) None of the above
Q.4 The correct order for the synthesis of the drug Phenylephrine is?
I. Reduction
II. Reaction with sodium hydride
III. Nitration
IV. 3-(benzyloxy)benzaldehyde reacts with ethylbromoacetate
a) IV – III – II – I
b) II – IV – I – III
c) IV – II – I – III
d) IV – III – I – II
Q.5 Predict the incorrect statements from the following with respect to the classification of the drug.
I. Phenylephrine is a selective α1-adrenergic agonist
II. Epinephrine is a nonselective adrenergic agonist
III. Norepinephrine is a nonselective adrenergic agonist
a) I, II & III
b) I & II
c) II only
d) All statements related to classification are correct
Q.6 The correct sequence of True and False for the given statements with respect to the drug Phenylephrine is-
I. Phenylephrine is a selective ß-adrenergic agonist.
II. It can be synthesized from 3-(benzyloxy)benzaldehyde
III. 3 chiral centers are present in its structure
IV. It is used as a decongestant.
a) FTTF
b) TFTF
c) FTFT
d) TFFT
Q.7 Which amongst the following drugs is having highest number of ring system in its structure-
a) Phenylephrine
b) Norepinephrine
c) Morphine
d) Penicillin G
1-b
2-a
3-a
4-d
5-d
6-c
7-c
REFERENCES
[1] Lemke TL, Zito SW, Roche VF, Williams DA. Essentials of Foye’s principles of medicinal chemistry. Wolters Kluwer; 2017, 340 [2] Lemke TL, Zito SW, Roche VF, Williams DA. Essentials of Foye’s principles of medicinal chemistry. Wolters Kluwer; 2017, 348-352
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