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]]>4-(2-aminopropyl)phenol
Hydroxyamphetamine is an indirect acting sympathomimetic amine drug having adrenergic properties.
S. NO. | PHYSICAL AND CHEMICAL PROPERTIES | |
1 | Molecular weight | 151.21 g/mol |
2 | Physical appearance | White to off-white crystalline powder |
3 | Melting point | 125.5°C |
4 | Solubility | Water solubility is 3.14 mg/ml |
5 | Presence of ring | Benzene ring |
6 | Number of chiral centers | 1 |
i. Hydroxyamphetamine causes release of norepinephrine from adrenergic nerve.
ii. This results in mydriasis. [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. 4-methoxybenzaldehyde and nitroethane reacts together in presence of primary amine to give 1-methoxy-4-((Z)-2-nitroprop-1-enyl)benzene.
ii. The latter compound in presence of iron and HCl gives 1-(4-methoxyphenyl)propan-2-one.
iii. On reaction with an amide, an unstable compound is produces which on treatment with HCl produces 1-(4-methoxyphenyl)propan-2-amine.
iv. On reaction with 40% HBr, hydroxyamphetamine is produced.
Hydroxyamphetamine is used:
Side effects of hydroxyamphetamine are:
Q.1 ”4-(2-aminopropyl)phenol” is the IUPAC nomenclature of which drug?
a) Hydroxyamphetamine
b) Ephedrine
c) Metaraminol
d) Propylhexedrine
Q.2 Physical appearance of Hydroxyamphetamine is?
a) Liqiud at room temperature
b) White to off-white crystalline powder
c) Red crystalline powder
d) Yelllow oily liquid at room temperature
Q.3 Match the following with correct classifications of the drugs.
i. Hydroxyamphetamine | A. Camptothecin analogue |
ii.Methotrexate | B. Folate antagonist antimetabolite |
iii. Phenoxybenzamine | C. Indirect acting sympathomimetic |
iv. Topotecan | D. Nonselective α-adrenergic antagonist |
a) i-B, ii-A, iii-D, iv-C
b) i-C, ii-A, iii-D, iv-B
c) i-D, ii-A, iiiB-, iv-C
d) i-C, ii-B, iii-D, iv-A
Q.4 Hydroxyamphetamine causes release of………… which results in ………..?
a) epinephrine, mydriasis
b) norepinephrine, mydriasis
c) acetylcholine, reduced blood pressure
d) acetycholine, increase in blood pressure
Q.5 Correct sequence for True and False for the given statements related with the SAR of drug…..
a) TF
b) FT
c) TT
d) FF
Q.6 Number of chiral centers present in the structure of Hydroxyamphetamine?
a) 0
b) 1
c) 2
d)3
Q.7 The drug Hydroxyamphetamine is mainly used for the diagnosis of?
a) Tumors
b) Kidney stone
c) Homer’s syndrome
d) None of the above
1-a
2-b
3-d
4-b
5-a
6-b
7-a
REFERENCES
[1] Gill JR, Mason DH, Bertter FC. Studies of the Natriuresis of Hydroxyamphetamine and on Its Mechanism of Action. Annals of Internal Medicine. 1966 May 1;64(5):1185. [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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