It07:Salbutamol

It07:Salbutamol

General
IUPAC Systematic name	2-(hydroxymethyl)-4-[1-hydroxy-2-(tert-butylamino)ethyl]phenol
Other names	Albuterol
Molecular formula	C₁₃H₂₁NO₃
Composition	C (65.25%) H( 8.84%) N (5.85%) O (20.06%)
SMILES	OC1=CC=C(C(O)CNC(C)(C)C)C=C1CO
CAS number	18559-94-9
Molar mass	239.31 gmol^-1
Appearance	A white or almost white, crystalline powder. Clear solution in methanol, very pale clear yellow solution.
Properties
Solubility	Sparingly soluble in water; soluble in ethanol (96%); slightly soluble in ether.
Melting point	157-158 °C (with decomposition)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Overiew

Salbutamol (INN), also known as albuterol, is a short-acting β₂-adrenergic receptor agonist which is used to deal with bronchospasms with symptoms of coughing, wheezing and shortness of breath, which are associated with lung-related problems like asthma, bronchitis and chronic obstructive pulmonary disease (COPD).

Salbutamol works by relaxing the muscles and the air passages in the lungs. Therefore air can flow into them much more freely to improve breathing.It does this by imitating the action of the hormone adrenaline (epinephrine).

Clinical use

Other uses for this medicine:

• Acute asthma

• Prevention of exercise-induced bronchospasm

• Hyperkalaemia, especially for those patients with renal failure

• Treat high potassium levels in patients with kidney failure

• Improve muscle paralysis in patients having a condition that causes occasional paralysis

• Used as a tocolytic to relax the uterine smooth muscel which delays the premature labour

Brand names

In general, salbutamol is usually sold under the brand names as following:

• Airomir

• Asthalin

• Asmol

• Buventol

• Proventil

• Salamol

• Sultanol

• Ventolin

• Volmax

Adverse effects

Symtoms of a salbutamol overdose:

• Angina or chet pain

• Headache

• Irregular heartbeats or a fluttering heart

• Nausea

• Seizures

• Tremor

• Vomiting

• Weakness

Salbutamol vs Adrenaline

In order to avoid dangerous side affect of adrenaline, for example increased cardiac arrhythmia, an extra carbon atom is added (labelled). A t-butyl group is added to increase the stability of the drug, so its effects last longer.

Synthesis Pathway

Salbutamol can be synthesised from Salicylic acid.

Spectra

NMR

References

1) http://en.wikipedia.org/wiki/Salbutamol

2) http://www.salbutamol.com/

3) "Organic Chemistry" Clayden et al