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| Routes of administration | Topical |
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| Pharmacokinetic data | |
| Metabolism | MAO,COMT |
| Excretion | Renal |
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| ECHA InfoCard | 100.002.506 |
| Chemical and physical data | |
| Formula | C9H11NO3 |
| Molar mass | 181.191 g·mol−1 |
| 3D model (JSmol) | |
| Melting point | 235 to 236 °C (455 to 457 °F) (decomposes) |
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Adrenalone is anadrenergic agonist used as a topicalvasoconstrictor andhemostatic. Formerly, it was also used to prolong the action oflocal anesthetics. It is theketone form ofepinephrine (adrenaline). Contrary to epinephrine, adrenalone mainly acts onalpha-1 adrenergic receptors, but has little affinity for beta receptors. The drug is largely obsolete, being superseded by other hemostatics such asthrombin,fibrinogen, andvasopressin analogues.[1]
Adrenalone does not stop bleeding from large blood vessels. It is not approved for systemic use. Combination withantithrombotics is not useful because they contravene the action of adrenalone.[1]
Vasoconstriction by adrenalone may lead to localnecrosis.[1]
Adrenalone passes into breast milk, but adverse effects are unlikely because of its very low systemic resorption.[1]
Adrenalone is a derivative of epinephrine, having the alcohol function replaced with a ketone. As a consequence, it is notoptically active any more.
Solubility in water,ethanol anddiethyl ether is low. The substance is typically used in form of thehydrochloride, a white crystalline powder which tastes bitter and slightly acidic, and is soluble in water (1:8) and 94% ethanol (1:45). The melting point of the hydrochloride is 243 °C (469 °F).[1]
After local application, only traces of adrenalone are found in the blood, which is partly a consequence of the vasoconstriction caused by the drug via alpha-1 adrenergic receptors. In an (unspecified) pharmacological model,hypertensive (blood pressure increasing) action has been found to be about 0.5% that of epinephrine at equivalent plasma concentrations. Therefore, systemic effects are unlikely.
Like epinephrine, adrenalone is metabolised bycatechol-O-methyl transferase (COMT), yielding 3O-methyladrenalone, which in turn is N-demethylized bymonoamine oxidase (MAO). Alternatively, it can first undergo metabolization by MAO and then by COMT; in both cases, the resulting 3O-methyl-N-demethyladrenalone is conjugated tosulfate orglucuronide and excreted by the kidney. No reduction to epinephrine has been observedin vivo.[1]