U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C9H11NO3
Molecular Weight 181.1889
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ADRENALONE

SMILES

CNCC(=O)c1ccc(c(c1)O)O

InChI

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

HIDE SMILES / InChI

Molecular Formula C9H11NO3
Molecular Weight 181.1889
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Adrenalone is a keton form of the natural substrate epinephrine. Adrenalone is evidently formed in vivo by hydrolytic cleavage of the diester by esterases. It is an adrenergic receptor agonist. Adrenalone inhibits the norepinephrine synthesis and dopamine beta oxidase. It is known to have very weak sympathomimetic activity when compared to adrenaline. Adrenalone has the high radioprotective effect. It is a topical nasal decongestant. Adrenalone has hemostatic, sympathomimetic and vasoconstrictor therapeutic functions.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Primary
Stryphnon

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Analysis of USP epinephrine injections for potency, impurities, degradation products, and d-enantiomer by liquid chromatography, using ultraviolet and electrochemical detectors.
1985 Mar-Apr
Modified syntheses of dopamine-4-sulfate, epinephrine-3-sulfate, and norepinephrine-3-sulfate: determination of the position of the sulfate group by 1H-NMR spectroscopy.
1988 Aug
Patents

Sample Use Guides

Mice: 50-150 mumol/kg
Route of Administration: Unknown
Substrate uptake by norepinephrine transporter was reduced to 99% (27%) at 10-uM (100-uM) concentrations of adrenalone; the half maximal inhibitory concentration (IC50) value of adrenalone was 36.9 uM.
Substance Class Chemical
Created
by admin
on Sat Jun 26 05:17:12 UTC 2021
Edited
by admin
on Sat Jun 26 05:17:12 UTC 2021
Record UNII
EGU41QL329
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ADRENALONE
INN   MART.   MI   USAN   WHO-DD  
INN   USAN  
Official Name English
ETHANONE, 1-(3,4-DIHYDROXYPHENYL)-2-(METHYLAMINO)-
Systematic Name English
ADRENALONE [USP]
Common Name English
3',4'-DIHYDROXY-2-(METHYLAMINO)ACETOPHENONE
Systematic Name English
ADRENALONE [INN]
Common Name English
NSC-243611
Code English
ADRENALINE TARTRATE IMPURITY C [EP]
Common Name English
ADRENONE
Common Name English
ADRENALONE [MI]
Common Name English
ADRENALONE [USAN]
Common Name English
ADRENALONE [MART.]
Common Name English
ADRENALONE [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-ATC A01AD06
Created by admin on Sat Jun 26 05:17:12 UTC 2021 , Edited by admin on Sat Jun 26 05:17:12 UTC 2021
WHO-ATC B02BC05
Created by admin on Sat Jun 26 05:17:12 UTC 2021 , Edited by admin on Sat Jun 26 05:17:12 UTC 2021
WHO-VATC QB02BC05
Created by admin on Sat Jun 26 05:17:12 UTC 2021 , Edited by admin on Sat Jun 26 05:17:12 UTC 2021
WHO-VATC QA01AD06
Created by admin on Sat Jun 26 05:17:12 UTC 2021 , Edited by admin on Sat Jun 26 05:17:12 UTC 2021
NCI_THESAURUS C87053
Created by admin on Sat Jun 26 05:17:12 UTC 2021 , Edited by admin on Sat Jun 26 05:17:12 UTC 2021
Code System Code Type Description
EVMPD
SUB05279MIG
Created by admin on Sat Jun 26 05:17:12 UTC 2021 , Edited by admin on Sat Jun 26 05:17:12 UTC 2021
PRIMARY
PUBCHEM
7436
Created by admin on Sat Jun 26 05:17:12 UTC 2021 , Edited by admin on Sat Jun 26 05:17:12 UTC 2021
PRIMARY
CAS
99-45-6
Created by admin on Sat Jun 26 05:17:12 UTC 2021 , Edited by admin on Sat Jun 26 05:17:12 UTC 2021
PRIMARY
EPA CompTox
99-45-6
Created by admin on Sat Jun 26 05:17:12 UTC 2021 , Edited by admin on Sat Jun 26 05:17:12 UTC 2021
PRIMARY
RXCUI
17073
Created by admin on Sat Jun 26 05:17:12 UTC 2021 , Edited by admin on Sat Jun 26 05:17:12 UTC 2021
PRIMARY RxNorm
FDA UNII
EGU41QL329
Created by admin on Sat Jun 26 05:17:12 UTC 2021 , Edited by admin on Sat Jun 26 05:17:12 UTC 2021
PRIMARY
MERCK INDEX
M1430
Created by admin on Sat Jun 26 05:17:12 UTC 2021 , Edited by admin on Sat Jun 26 05:17:12 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL2103996
Created by admin on Sat Jun 26 05:17:12 UTC 2021 , Edited by admin on Sat Jun 26 05:17:12 UTC 2021
PRIMARY
DRUG BANK
DB13394
Created by admin on Sat Jun 26 05:17:12 UTC 2021 , Edited by admin on Sat Jun 26 05:17:12 UTC 2021
PRIMARY
INN
3174
Created by admin on Sat Jun 26 05:17:12 UTC 2021 , Edited by admin on Sat Jun 26 05:17:12 UTC 2021
PRIMARY
NCI_THESAURUS
C81339
Created by admin on Sat Jun 26 05:17:12 UTC 2021 , Edited by admin on Sat Jun 26 05:17:12 UTC 2021
PRIMARY
ECHA (EC/EINECS)
202-756-9
Created by admin on Sat Jun 26 05:17:12 UTC 2021 , Edited by admin on Sat Jun 26 05:17:12 UTC 2021
PRIMARY
DRUG CENTRAL
96
Created by admin on Sat Jun 26 05:17:12 UTC 2021 , Edited by admin on Sat Jun 26 05:17:12 UTC 2021
PRIMARY
MESH
C040224
Created by admin on Sat Jun 26 05:17:12 UTC 2021 , Edited by admin on Sat Jun 26 05:17:12 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY