Adrenaline sulfation

Tyrosine (Tyr or Y) (4-hydroxyphenylalanine ((5)-2-amino-3-(4-hydroxyphenyl)-propanoic acid)) is a polar, neutral, aromatic amino acid with the formula H00CCH(NH2)CH2C6H50H and is the precursor of thyroxin, dopamine, norepinephrine (noradrenaline), epinephrine (adrenaline), and the pigment melanin. Being the precursor amino acid for the thyroid gland hormone thyroxin, a defect in this may result in hypothyroidism. Tyr is extremely soluble in water, a property that has proven useful in isolating this amino acid from protein hydrolysates. The occurrence of tyrosine- 0-sulfate as a constituent of human urine and fibrinogen has been reported. ... 

Warfarin sodium may be adsorbed to PVC and intravenous infusion sets but may be minimized with glass containers or polyethylene-lined containers. Warfarin sodium is incompatible with solutions of adrenaline hydrochloride, amikacin sulfate, metaraminol tartrate, oxytocin, promazine hydrochloride, tetracycline hydrochloride, aminophylline, bretylium tosylate, ceftazidime, cimetidine hydrochloride, ciprofloxacin lactate, dobutamine hydrochloride, esmolol hydrochloride, gentamicin sulfate, labetalol hydrochloride, metronidazole hydrochloride, and vancomycin hydrochloride.130131... 

A 22-year-old woman with mild asthma developed severe laryngospasm and bronchoconstriction after a fourth and subsequent doses of nebulized salbutamol, given during an acute episode of asthma. Her symptoms responded to adrenaline, but recurred after supervised rechallenge with nebulized orciprenaline (metaproter-enol) sulfate. Indirect laryngoscopy excluded vocal cord dysfunction, suggesting that her symptoms of severe wheeze, respiratory distress, and hypoxia were due to bronchoconstriction. 

Quinuronium sulfate is a bitter, white to yellow, crystalline powder that is usually available as a stable 5% aqueous solution. This compound is effective in the treatment of B. caballi infections but is associated with relapses, making it more effective for premunition than for the elimination of infection. One treatment consists of two doses of a 5% solution of quinuronium sulfate, administered s.c. at 0.3mg/kg, 6h apart. Quinuronium sulfate has a narrow margin of safety and overdosing produces parasympathomimetic effects including tremors, salivation, urination and defecation. These signs usually respond to treatment with atropine, epinephrine (adrenaline) and calcium gluconate. The interval between treatments should not be shorter than 2 weeks and should preferably be 3 months because sensitization occurs, which results in shock, with a profound drop in blood pressure, and death. 

The principal sites for sulfation reactions are the liver and kidneys, although an important site, especially after oral administration of drugs, is the small intestine. Sulfation in the gut can seriously affect the bioavailability of some drugs such as paracetamol (see Figure 5.3) and is the main reason why adrenaline (epinephrine) is not effective when given orally... 

Figure 3 Separation of noradrenaline (NA), adrenaline (A), di-hydroxybenzylamine (DBH), and dopamine (DA), 0.65 pmol each. Stationary phase LiChrosorb RP18, Sum. Mobile phase 3,5-dimethylcyclohexyl sulfate 2 x 10 moll and 8% of methanol in citrate-acetate buffer solution, pH 5.2. Electrochemical detection at -I-0.7V.

Esaka, Y, Tanaka, K., Uno, B., and Goto, M. 1997. Sodium dodecyl sulfate Tween 20 mixed micellar electrokinetic chromatography for separation of hydrophobic cations Application to adrenaline and its precursors. AwaZ. Chem. 69 1332-1338. 

Adrenaline (XXV) is related to catechol and the naturally occurring (levorotatory) form, which is the adrenal hormone, finds extensive use in medicine. Dodgson, Garton and Williams (85, 86) questioned the conclusion of Deichmann (70) that i-adrenaline is excreted by rabbits wholly as a sulfate and not as a glucuronoside and showed that about 21 per cent of d-adrenaline is excreted as a glucuronoside, the amount excreted as a sulfate being insignificant. 

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