Adrenalone

Short description: Chemical compound

Adrenalone

Clinical data
Pregnancy
category|

* No data

Routes of
administration| Topical
ATC code|

* A01AD06 (WHO) B02BC05 (WHO)

Pharmacokinetic data
Metabolism| MAO, COMT
Excretion| Renal
Identifiers

IUPAC name

* 1-(3,4-dihydroxyphenyl)-2-(methylamino)ethanone

CAS Number|

* 99-45-6 N
62-13-5 (hydrochloride)

PubChem CID|

* 7436

ChemSpider|

* 7158 Y

UNII|

* EGU41QL329

KEGG|

* D02774 Y

ChEMBL|

* ChEMBL2103996 N

Chemical and physical data
Formula| C9H11NO3
Molar mass| 181.191 g·mol−1
3D model (JSmol)|

* Interactive image

Melting point| 235 to 236 °C (455 to 457 °F) (decomposes)

SMILES

* O=C(c1cc(O)c(O)cc1)CNC

InChI

* InChI=1S/C9H11NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,10-12H,5H2,1H3 Y

* Key:PZMVOUYYNKPMSI-UHFFFAOYSA-N Y

NY (what is this?) (verify)

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 The drug is largely obsolete, being superseded by other hemostatics such as thrombin, fibrinogen, and vasopressin analogues.[1]

## Contents

* 1 Contraindications and interactions
* 2 Side effects
* 3 Pregnancy and lactation
* 4 Chemical properties
* 5 Pharmacology
* 6 References

## 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]

## References

1. ↑ 1.0 1.1 1.2 1.3 1.4 1.5 (in German) Arzneistoff-Profile. 4 (23 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. 2010. ISBN 978-3-7741-9846-3.

* v
* t
* e

Stomatological preparations (A01)

Caries prophylaxis|

* Dectaflur
* Olaflur
* Sodium fluoride
* Sodium monofluorophosphate
* Stannous fluoride

Infection and antiseptics|

* Amphotericin B
* Benzoxonium chloride
* Chlorhexidine
* Chlortetracycline
* Clotrimazole
* Cetylpyridinium chloride
* Domiphen bromide
* Doxycycline
* Eugenol
* Hexetidine
* Hydrogen peroxide
* Mepartricin
* Metronidazole
* Miconazole
* Minocycline
* Natamycin
* Neomycin
* Oxyquinoline
* Polynoxylin
* Sodium perborate
* Tetracycline
* Tibezonium iodide

Corticosteroids
(Glucocorticoids)|

* Dexamethasone
* Hydrocortisone
* Triamcinolone

Other|

* Amlexanox
* Acetylsalicylic acid
* Becaplermin
* Benzydamine
* Epinephrine/Adrenalone

* v
* t
* e

Antihemorrhagics (B02)

Antihemorrhagic|

| Systemic|

| Vitamin K|

* Phytomenadione (K1)
* Menadione (K3)

|

Coagulation
factors|

* intrinsic: IX/Nonacog alfa
* VIII/Moroctocog alfa/Turoctocog alfa

* extrinsic: VII/Eptacog alfa

* common: X
* II/Thrombin
* I/Fibrinogen
* XIII/Catridecacog

* combinations: Prothrombin complex concentrate (II, VII, IX, X, protein C and S)

Other
systemic|

* Batroxobin
* Carbazochrome
* Etamsylate
* Fostamatinib
* thrombopoietin receptor agonist
* Romiplostim
* Avatrombopag
* Eltrombopag
* Lusutrombopag

Local|

* Absorbable gelatin sponge
* Oxidized cellulose
* Tetragalacturonic acid hydroxymethylester
* Thrombin
* Collagen
* Calcium alginate
* Epinephrine/Adrenalone

Antifibrinolytics|

* amino acids
* Aminocaproic acid
* Tranexamic acid
* Aminomethylbenzoic acid
* serpins
* Aprotinin
* Alfa1 antitrypsin
* C1-inhibitor
* Camostat
* unsorted
* Ulinastatin

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