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{{Drugbox
{{Drugbox
| IUPAC_name       = 1-(3,4-dihydroxyphenyl)-2-methylaminoethanone
| Verifiedfields = changed
| image             = Adrenalone.svg
| verifiedrevid = 477243041
| CAS_number        = 99-45-6
| IUPAC_name = 1-(3,4-dihydroxyphenyl)-2-(methylamino)ethanone
| ATC_prefix        = A01
| image = Adrenalone Wiki Str.png
| ATC_suffix        = AD06
 
| ATC_supplemental  = {{ATC|B02|BC05}}
 
| PubChem          = 7436
<!--Clinical data-->
| DrugBank          =
| tradename =   
| C=9|H=11|N=1|O=3
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| molecular_weight = 181.189 g/mol
| pregnancy_US = <!-- A / B            / C / D / X -->
| bioavailability  =
| pregnancy_category = No data
| protein_bound    =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| metabolism        =
| legal_CA = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| elimination_half-life =
| legal_UK = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| excretion        =
| legal_US = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| pregnancy_AU     = <!-- A / B1 / B2 / B3 / C / D / X -->
| legal_status = 
| pregnancy_US     = <!-- A / B            / C / D / X -->
| routes_of_administration = Topical
| pregnancy_category=
 
| legal_AU         = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
<!--Pharmacokinetic data-->
| legal_CA         = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| bioavailability = 
| legal_UK         = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| protein_bound = 
| legal_US         = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| metabolism = [[Monoamine oxidase|MAO]], [[Catechol-O-methyl transferase|COMT]]
| legal_status      =  
| elimination_half-life = 
| routes_of_administration =  
| excretion = [[Renal]]
 
<!--Identifiers-->
| CAS_number_Ref = {{cascite|changed|??}}
| CAS_number = 99-45-6
| CAS_supplemental = <br />{{CAS|62-13-5}} ([[hydrochloride]])
| ATC_prefix = A01
| ATC_suffix = AD06
| ATC_supplemental =  {{ATC|B02|BC05}}
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 2103996
| PubChem = 7436
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = 
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 7158
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = EGU41QL329
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D02774
 
<!--Chemical data-->
| C=9 | H=11 | N=1 | O=3
| molecular_weight = 181.189 g/mol
| smiles = O=C(c1cc(O)c(O)cc1)CNC
| InChI = 1/C9H11NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,10-12H,5H2,1H3
| InChIKey = PZMVOUYYNKPMSI-UHFFFAOYAW
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C9H11NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,10-12H,5H2,1H3
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = PZMVOUYYNKPMSI-UHFFFAOYSA-N
| melting_point    = 235
| melting_high     = 236
| melting_notes    = ([[Chemical decomposition|decomposes]])
}}
}}
__NOTOC__
{{SI}}
{{SI}}
{{CMG}}
{{CMG}}
== Overview ==


'''Adrenalone''' is an [[adrenergic agonist]] used as a topical [[vasoconstrictor]] and [[hemostatic]]. Formerly, it was also used to prolong the action of [[local anesthetic]]s. It is the [[ketone]] form of [[epinephrine]] (adrenaline). Contrary to epinephrine, adrenalone mainly acts on [[alpha-1 adrenergic receptor]]s, but has little affinity for beta receptors. The drug is largely obsolete, being superseded by other hemostatics such as [[thrombin]], [[fibrinogen]], and [[vasopressin analogue]]s.<ref name="Arzneistoff-Profile">
{{cite book
| title        = Arzneistoff-Profile
| editor1-last = Dinnendahl | editor1-first = V.
| editor2-last = Fricke    | editor2-first = U.
| publisher    = Govi Pharmazeutischer Verlag
| location    = Eschborn, Germany
| date        = 2010
| edition      = 23
| volume      = 4
| isbn        = 978-3-7741-9846-3
| language    = German
}}</ref>


==Contraindications and interactions==
Adrenalone does not stop bleeding from large blood vessels. It is not approved for systemic use. Combination with [[antithrombotic]]s is not useful because they contravene the action of adrenalone.<ref name="Arzneistoff-Profile" />


'''Adrenalone''' is an [[adrenergic agonist|adrenergic agent]] used as a topical [[vasoconstrictor]] and [[hemostatic]]. It is the [[ketone]] form of [[epinephrine]].
==Side effects==
Vasoconstriction by adrenalone may lead to local [[necrosis]].<ref name="Arzneistoff-Profile" />
 
==Pregnancy and lactation==
Adrenalone passes into breast milk, but adverse effects are unlikely because of its very low systemic resorption.<ref name="Arzneistoff-Profile" />
 
==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 {{convert|243|°C|°F}}.<ref name="Arzneistoff-Profile" />
 
==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''.<ref name="Arzneistoff-Profile" />
 
==References==
{{reflist|2}}


{{Stomatological preparations}}
{{Stomatological preparations}}
{{Antihemorrhagics}}
{{Antihemorrhagics}}
[[Category:drug]]
[[Category:Catecholamines]]
[[Category:Catecholamines]]
[[Category:Sympathomimetics]]
[[Category:Aromatic ketones]]
[[Category:Hematology]]
 
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Latest revision as of 17:15, 18 August 2015

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
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC9H11NO3
Molar mass181.189 g/mol
3D model (JSmol)
Melting point235 to 236 °C (Expression error: Unrecognized word "to". °F) (decomposes)
 ☒N☑Y (what is this?)  (verify)

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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

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]

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 (469.4 °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 Dinnendahl, V.; Fricke, U., eds. (2010). Arzneistoff-Profile (in German). 4 (23 ed.). Eschborn, Germany: Govi Pharmazeutischer Verlag. ISBN 978-3-7741-9846-3.
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