Adrenalone

Title: Adrenalone
CAS Registry Number: 99-45-6
CAS Name: 1-(3,4-Dihydroxyphenyl)-2-(methylamino)ethanone
Additional Names: 3¢,4¢-dihydroxy-2-(methylamino)acetophenone; 3,4-dihydroxy-a-methylaminoacetophenone; adrenone; 4-methylaminocetopyrocatechol
Trademarks: Stryphnon (Salus-Braumapharm)
Molecular Formula: C9H11NO3
Molecular Weight: 181.19
Percent Composition: C 59.66%, H 6.12%, N 7.73%, O 26.49%
Literature References: Intermediate in some epinephrine manuf processes. Prepd from 4-chloroacetylpyrocatechol and methylamine: DE 152814 (Hoechst); Stolz, Ber. 37, 4152 (1904); by heating a-(p-toluene sulfonylmethylamino)-3,4-dimethoxyacetophenone with HCl under pressure: DE 277540 (Bayer); Frdl. 12, 764; Chem. Zentralbl. 1914, II, 740.
Properties: Needles, dec 235-236°. Sparingly sol in water, alc, ether.
Derivative Type: Hydrochloride
CAS Registry Number: 62-13-5
Trademarks: Stryphnasal (Sertner)
Molecular Formula: C9H11NO3.HCl
Molecular Weight: 217.65
Percent Composition: C 49.67%, H 5.56%, N 6.44%, O 22.05%, Cl 16.29%
Properties: Crystals, mp 243°. Freely sol in water; sol in alcohol. Insol in ether. Aq solns are neutral to litmus.
Melting point: mp 243°
Therap-Cat: Hemostatic.
Keywords: a-Adrenergic Agonist; Hemostatic.
Adrenochrome Adrenoglomerulotropin Adrenolutin Adrenomedullin Aequorin

Adrenalone
Adrenalone.svg
Systematic (IUPAC) name
1-(3,4-dihydroxyphenyl)-2-(methylamino)ethanone
Clinical data
Pregnancy cat. No data
Legal status  ?
Routes Topical
Pharmacokinetic data
Metabolism MAO, COMT
Excretion Renal
Identifiers
CAS number 99-45-6 N
62-13-5 (hydrochloride)
ATC code A01AD06 B02BC05
PubChem CID 7436
ChemSpider 7158 YesY
UNII EGU41QL329 YesY
KEGG D02774 YesY
Chemical data
Formula C9H11NO3 
Mol. mass 181.189 g/mol
Physical data
Melt. point 235–236 °C (455–457 °F) (decomposes)
 N (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 The drug is largely obsolete, being superseded by other hemostatics such as thrombin, fibrinogen, and vasopressin analogues.[1]