ADRENALONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H11NO3
Molecular Weight	181.1885
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CNCC(=O)C1=CC=C(O)C(O)=C1

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	181.1885
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21885739 | http://en.pharmacodia.com/web/drug/1_11686.html | https://www.ncbi.nlm.nih.gov/pubmed/6547911 | https://www.ncbi.nlm.nih.gov/pubmed/9467647 | https://www.ncbi.nlm.nih.gov/pubmed/13899911 | (2013) Pharmaceutical Manufacturing Encyclopedia, page 112, retrieved from: https://books.google.ru/books?id=_J2ti4EkYpkC

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Dopamine beta-hydroxylase 17 Target ID: CHEMBL3102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13899905	Inhibitor 8504
Norepinephrine synthesis 2 Target ID: Norepinephrine synthesis Sources: https://www.ncbi.nlm.nih.gov/pubmed/13899911	Inhibitor 8504
Adrenergic receptor alpha 65 Target ID: CHEMBL2095203 Sources: Milne, G. W. A. (2017) Drugs: Synonyms and Properties, retrieved from: https://books.google.ru/books?id=RlM8DwAAQBAJ	Agonist 2752

Conditions

Condition	Modality	Highest Phase	Product
Asthma 244 Sources: https://www.ncbi.nlm.nih.gov/pubmed/13136023	Primary	Not Provided 511	Unknown Approved Use Unknown
Radiation sickness 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9467647	Preventing	Preclinical	Unknown Approved Use Unknown
Glaucoma 57 Sources: http://en.pharmacodia.com/web/drug/1_11686.html	Primary	Approved 8583	Stryphnon Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B3-041179	http://www.3bsc.com/index/pro_info.php?id=63352
AA Blocks	AA005S8J	https://www.aablocks.com/goods/Goods/detail?id=AA005S8J
Achemo Scientific Limited	AC-88652	http://www.achemo.com/search/?Keyword= 99-45-6
AHH Chemical co.,ltd	MT-09913	http://www.ahhchemical.com/product/MT-09913.html
AK Scientific, Inc. (AKSCI)	Q759	http://www.aksci.com/item_detail.php?cat=Q759
Alinda	ALBB-025687	http://alinda.ru/finechem_en_.html?i=ALBB-025687
Angene	AGN-PC-0JK836	http://www.angenechemical.com/productshow/AGN-PC-0JK836.html
Aurora Fine Chemicals LLC	A00.738.009	http://online.aurorafinechemicals.com/info?ID=A00.738.009
Aurum Pharmatech LLC	NE62917	http://www.Aurumpharmatech.com/Product/ProductDetails/NE62917
BioSynth	J-519543	https://www.biosynth.com/en/products/all-products/products/J-519543.html
ChemMol	30100025	http://www.chemmol.com/chemmol/30100025.html
ChemMol	44000027	http://www.chemmol.com/chemmol/44000027.html
Chemspace	CSSS00000032228	https://chem-space.com/CSSS00000032228
Clearsynth	CS-T-64914	https://www.clearsynth.com/en/CST64914.html
Debye Scientific	DB-057784	http://www.debyesci.com/cas_99-45-6.html
eNovation Chemicals	D670654	https://www.enovationchem.com/ProductDetails.asp?ProductID=D670654
eNovation Chemicals	Y1077926	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y1077926
Finetech	FT-0631521	http://www.finetechnology-ind.com/prod/detail/pub/99-45-6.html
Hairui	HR104465	http://www.hairuichem.com/en/product/99-45-6.html
iChemical	EBD46411	http://www.ichemical.com/chemicals/cas-99-45-6
Lab Network	LN00239137	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00239137
mcule	MCULE-5219258762	https://mcule.com/MCULE-5219258762/
MolPort	MolPort-001-785-703	https://www.molport.com/shop/molecule-link/MolPort-001-785-703
Renno Tech	RP24238	http://www.rennotech.com/product_show.asp?id=29892
Sinfoo Biotech	S017973	http://www.sinfoobiotech.com/product/1021371
Smolecule	S517315	http://www.smolecule.com/products/s517315
Synblock Inc	AB06968	http://www.synblock.com/product/99-45-6.html
THE BioTek	bt-258288	https://www.thebiotek.com/product/inhibitors/bt-258288
TimTec	SBB072639	http://www.echemstore.com/sbb072639-1-3-4-dihydroxyphenyl-2-methylamino-ethan-1-one.html
TimTec	ST45028726	http://www.echemstore.com/st45028726-1-3-4-dihydroxyphenyl-2-methylamino-ethan-1-one.html
Yuhao Chemical	HL1306	http://www.chemyuhao.com/99-45-6.html

PubMed

Title	Date	PubMed
[Radiation protective effect of beta-ketoanalogs of hydroxyphenyl ethanolamines].	1998-02-19	9467647
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.	1988-08	3182167
Analysis of USP epinephrine injections for potency, impurities, degradation products, and d-enantiomer by liquid chromatography, using ultraviolet and electrochemical detectors.	1985-03-01	3988695
Improved Delivery Through Biological Membranes. XVII. A Site-Specific Chemical Delivery System as a Short-Acting Mydriatic Agent.	1984-07	24277286
Formation of adrenaline in the iris-ciliary body from adrenalone diesters.	1984-06	6547911
Electron spin resonance-spin stabilization of semiquinones produced during oxidation of epinephrine and its analogues.	1984-01-10	6323406

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 50-150 mumol/kg

Route of Administration: Unknown

In Vitro Use Guide

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 `Mon Mar 31 18:21:02 GMT 2025` Edited by `admin` on `Mon Mar 31 18:21:02 GMT 2025`
Record UNII	EGU41QL329
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-243611

Preferred Name

English

ADRENALONE

Official Name

English

1-(3,4-DIHYDROXYPHENYL)-2-(METHYLAMINO)ETHANONE

Systematic Name

English

ETHANONE, 1-(3,4-DIHYDROXYPHENYL)-2-(METHYLAMINO)-

Systematic Name

English

ADRENALINE TARTRATE IMPURITY C [EP IMPURITY]

Common Name

English

3',4'-DIHYDROXY-2-(METHYLAMINO)ACETOPHENONE

Systematic Name

English

adrenalone [INN]

Common Name

English

ADRENONE

Common Name

English

Adrenalone [WHO-DD]

Common Name

English

ADRENALONE [MI]

Common Name

English

ADRENALONE [USP IMPURITY]

Common Name

English

ADRENALONE [USAN]

Common Name

English

ADRENALONE [MART.]

Common Name

English

ADRENALINE IMPURITY C [EP IMPURITY]

Common Name

English

Classification Tree Code System Code

WHO-ATC

A01AD06