Adrenalone

Adrenalone is an adrenergic agonist used as a topical vasoconstrictor and hemostatic. Formerly, it was also used to prolong the action of local anesthetics. It is the ketone form of epinephrine (adrenaline). Contrary to epinephrine, adrenalone mainly acts on alpha-1 adrenergic receptors, but has little affinity for beta receptors. The drug is largely obsolete, being superseded by other hemostatics such as thrombin, fibrinogen, and vasopressin analogues.[1]

Adrenalone
Clinical data
Pregnancy
category
  • No data
Routes of
administration		Topical
ATC code
Pharmacokinetic data
MetabolismMAO, COMT
ExcretionRenal
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.002.506
Chemical and physical data
FormulaC9H11NO3
Molar mass181.191 g·mol−1
3D model (JSmol)
Melting point235 to 236 °C (455 to 457 °F) (decomposes)
 NY (what is this?)  (verify)

Contraindications and interactions

Adrenalone does not stop bleeding from large blood vessels. It is not approved for systemic use. Combination with antithrombotics is not useful because they contravene the action of adrenalone.[1]

Side effects

Vasoconstriction by adrenalone may lead to local necrosis.[1]

Pregnancy and lactation

Adrenalone passes into breast milk, but adverse effects are unlikely because of its very low systemic resorption.[1]

Chemical properties

Adrenalone is a derivative of epinephrine, having the alcohol function replaced with a ketone. As a consequence, it is not optically active any more.

Solubility in water, ethanol and diethyl ether is low. The substance is typically used in form of the hydrochloride, 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]

Pharmacology

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 by catechol-O-methyl transferase (COMT), yielding 3O-methyladrenalone, which in turn is N-demethylized by monoamine 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 to sulfate or glucuronide and excreted by the kidney. No reduction to epinephrine has been observed in vivo.[1]

gollark: I mean "simple" as in "one recipe for each item, no muultiple-output recipes, no loops", which is quite limiting.
gollark: Very simple autocrafting *is* doable without huge problems - Dragon had an implementation - but that's not very good.
gollark: Are you suggesting we should cover anything but the maximally general case? HERESY!
gollark: In fact, not only is it computationally NP-hard, apparently (Squid did some insanity here: https://squiddev.cc/2018/01/28/ae-sat.html), but to do it *well* you also have to somehow make highly subjective decisions!
gollark: Auto-crafting turns out to be extremely hard.

References
  1. Dinnendahl, V.; Fricke, U., eds. (2010). Arzneistoff-Profile (in German). 4 (23 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. ISBN 978-3-7741-9846-3.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.