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]]>3-[(1R,2S)-2-amino-1-hydroxypropyl]phenol.
Metaraminol is a selective α1- adrenergic agonist.
S. NO. | PHYSICAL AND CHEMICAL PROPERTIES | |
1 | Molecular weight | 167.2 g/mol |
2 | Physical appearance | Present in solid form |
3 | Melting point | 107.5°C |
4 | Solubility | 1000g/L |
5 | Octanol/water partition coefficient | -0.27 |
6 | Presence of ring | Benzene ring |
7 | Number of chiral centers | 2 |
i. Metaraminol acts as α1-drenergic agonist and produces peripheral vasoconstriction.
ii. It inhibits adenyl cyclase and thus, inhibition of the production of cAMP
iii. It also releases norepinephrine from its storage sites indirectly.
iv. All results in increase in systemic blood pressure. [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. 1-(3-hydroxyphenyl)propan-1-one is reacted with chlorobenzene to give 1-(3-(benzyloxy)phenyl)propan-1-one.
ii. Reaction of the above compound with BnONO gives (E)-1-(3-(benzyloxy)phenyl)-2-(hydroxyimino)propan-1-one.
iii. When the latter compound undergoes reduction, it produces 2-amino-1-(3-(benzyloxy) phenyl)propan-1-ol.
iv. Latter compound further undergoes reduction to give Metaraminol.
Ephedrine is used:
Side effects of metaraminol are:
MCQs
Q.1 Complete the given below sentence.
“Metaraminol acts on α-adrenergic receptors and leads to ……… of adenylcyclase, thus inhibition of production of ………. .
a) Stimulation, ATP
b) Inhibition, cAMP
c) Stimulation, cAMP
d) Inhibition, ATP
Q.2 Metaraminol is given to patient during?
a) Hypotension
b) Hypertension
c) Tachycardia
d) None of these
Q.3 Which amongst the following are the correct statements with respect to the SAR of drug Metaraminol?
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.4 The starting chemicals required for the synthesis of drug Metaraminol?
a) 1-(3-hydroxyphenyl)propan-1-one
b) 3-(4-nitrophenyl)butanone
c) Both a) and b) are required
d) None of these
Q.5 Correct sequence for the True/False for the physiochemical properties of the drug Metaraminol?
I. Molecular weight is 121.25 gm/mol
II. Its solubility is 1000 gm/L
III. Melts at room temperature.
IV. Cyclohexyl ring is present in the structure.
a) TFTF
b) TTFT
c) TTFF
d)FFTT
Q.6 Correct statements for the IUPAC nomenclatures of the drugs are?
I. Metaraminol: 3-[(1R,2S)-2-amino-1-hydroxypropyl]phenol
II. Pseudoephedrine: (S,S)-2-methylamino-1-phenylpropan-1-ol.
III. Hydroxyamphetamine: (RS)-[4-(1-Hydroxy-2-tert-butylamino-ethyl)-2-(4-methylbenzoyl)oxy-phenyl] 4-methylbenzoate
a) I, III
b) I, II
c) I, II, III
d) II, III
Q.7 Match the following drugs with their correct classifications-
i. Metaraminol | A. Mixed-acting sympathomimetic |
ii. Amphetamine | B. ß2-arenergic agonist |
iii. Silodosin | C. Selective α1-adenergic agonist |
iv. Pirbuterol | D. Selective α2-adrenergic antagonist |
a) i-D, ii-A, iii-C, iv-B
b) i-C, ii-A, iii-B, iv-D
c) i-B, ii-D, iii-C, iv-A
d) i-C, ii-A, iii-D, iv-B
1-b
2-a
3-c
4-a
5-c
6-b
7-d
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