METANEPHRINE, (+/-)

Details

Stereochemistry	RACEMIC
Molecular Formula	C10H15NO3
Molecular Weight	197.231
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=JWJCTZKFYGDABJ-UHFFFAOYSA-N

InChI=1S/C10H15NO3/c1-11-6-9(13)7-3-4-8(12)10(5-7)14-2/h3-5,9,11-13H,6H2,1-2H3

HIDE SMILES / InChI

Molecular Formula	C10H15NO3
Molecular Weight	197.231
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15317907

Metanephrine (metadrenaline) is a metabolite of epinephrine (adrenaline) created by the action of catechol-O-methyl transferase on epinephrine. It is a commonly occurring, pharmacologically and physiologically inactive metabolite of epinephrine. The measurement of plasma free metanephrines is considered to be the best tool in the diagnosis of pheochromocytoma, a rare kind of adrenal medullary neoplasm. In adrenal chromaffin cells, leakage of norepinephrine and epinephrine from storage granules leads to the substantial intracellular production of the O-methylated metabolite metanephrine. In fact, the adrenals constitute the single largest source out of any organ system including the liver for circulating metanephrine. In humans, about 93 percent of circulating metanephrine is derived from catecholamines metabolized within adrenal chromaffin cells.

CNS Activity

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Solute carrier family 22 member 1 18 Target ID: CHEMBL5685 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10344529	Inhibitor 8504		34.2 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pheochromocytoma 14 Sources: https://clinicaltrials.gov/ct2/show/NCT00843037	Diagnostic		Natural Metabolite	Unknown Approved Use Unknown
Paraganglioma 2 Sources: https://clinicaltrials.gov/ct2/show/NCT00843037	Diagnostic		Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
The significance of cystic adrenal lesions in multiple endocrine neoplasia IIB syndrome.	2004-10	15455172
[Adrenal incidentaloma associated to elevated urinary normethanephrine in a patient with high blood pressure].	2004-09-24	15382441
Paracetamol-associated interference in an HPLC-ECD assay for urinary free metadrenalines and catecholamines.	2004-07	15298744
Does iodine-131 meta-iodobenzylguanidine (MIBG) scintigraphy have an impact on the management of sporadic and familial phaeochromocytoma?	2004-07	15212651
Predictive value of preoperative transthoracic echocardiography in patients undergoing adrenalectomy for pheochromocytoma.	2004-07	15196103
Development of enantioselective immunoassays for free plasma metanephrines.	2004-06	15240418
Experience with surgical excision in childhood pheochromocytoma.	2004-06	15201507
The economic implications of three biochemical screening algorithms for pheochromocytoma.	2004-06	15181069
Pitfall in HPLC assay for urinary metanephrines: an unusual type of interference caused by methenamine intake.	2004-06	15161735
Plasma metanephrine levels are decreased in type 1 diabetic patients with a severely impaired epinephrine response to hypoglycemia, indicating reduced adrenomedullary stores of epinephrine.	2004-05	15126521
Diagnosis and localization of pheochromocytoma.	2004-05	15023935
Hormonal changes during long-term isolation.	2004-05	14722779
In vivo assessment of catechol O-methyltransferase activity in rabbit skeletal muscle.	2004-04-30	15182744
Labile hypertension, increased metanephrines and imaging misadventures.	2004-04	15031367
[Hypertension secondary to pheochromocytoma].	2004-03	15171431
Advances in metanephrine testing for the diagnosis of pheochromocytoma.	2004-03	15157558
Diagnosis and management of medullary thyroid carcinoma.	2004-03	15157557
Contactless conductivity detection of selected organic ions in on-chip electrophoresis.	2004-03	15004853
Measurement of plasma free metanephrine and normetanephrine by liquid chromatography-tandem mass spectrometry for diagnosis of pheochromocytoma.	2004-03	14726465
NIH state-of-the-science statement on management of the clinically inapparent adrenal mass ("incidentaloma").	2004-02-11	14768652
Phaeochromocytoma-induced myocarditis mimicking acute myocardial infarction.	2003-11	14686578
Stability of plasma free metanephrines during collection and storage as assessed by an optimized HPLC method with electrochemical detection.	2003-11	14578334
Phaeochromocytoma unmasked by drug therapy.	2003-10	14619898
Chiral on-chip separations of neurotransmitters.	2003-09-01	14632083
Diabetes as a marker of pheochromocytoma in hypertensive patients.	2003-09	12923403
Prolonged survival of a patient with multiple endocrine neoplasia type 2b and stage IV medullary thyroid carcinoma.	2003-08-15	12917093
A pitfall of metaiodobenzylguanidine scan: paraganglioma in close proximity to adrenocortical adenoma.	2003-08	12951637
Pheochromocytoma: state-of-the-art and future prospects.	2003-08	12920154
Exercise induces excessive normetanephrine responses in hypertensive diabetic patients.	2003-06	12795644
Screening for endogenous substrates reveals that CYP2D6 is a 5-methoxyindolethylamine O-demethylase.	2003-06	12777961
Sources and significance of plasma levels of catechols and their metabolites in humans.	2003-06	12649306
[Current management of pheochromocytoma: about 50 cases].	2003-05	12853019
Catecholamine functioning in children with traumatic brain injuries and children with attention-deficit/hyperactivity disorder.	2003-05	12706222
Plasma levels of catechols and metanephrines in neurogenic orthostatic hypotension.	2003-04-22	12707437
Adrenal cortical phaeochromocytoma: a case report of a rare entity.	2003-04	12746763
Catecholamines increase in the urine of non-segmental vitiligo especially during its active phase.	2003-04	12622787
A comparison of biochemical tests for pheochromocytoma: measurement of fractionated plasma metanephrines compared with the combination of 24-hour urinary metanephrines and catecholamines.	2003-02	12574179
Editorial: biochemical diagnosis of pheochromocytoma--is it time to switch to plasma-free metanephrines?	2003-02	12574178
Kinetic inhibitory profile of BIA 3-202, a novel fast tight-binding, reversible and competitive catechol-O-methyltransferase inhibitor.	2003-01-24	12559377
Microemulsion electrokinetic chromatographic analysis of some polar compounds.	2003-01-05	12450530
Pheochromocytoma: rediscovery as a catecholamine-metabolizing tumor.	2003	14586065
Effects of Qigong on blood pressure, blood pressure determinants and ventilatory function in middle-aged patients with essential hypertension.	2003	12943180
Twelve-year experience in the investigation and treatment of paragangliomas.	2002-12	12510946
Phaeochromocytoma with normal urinary catecholamines: the potential value of urinary free metadrenalines.	2002-11	12564837
Psychobiologic responses to 4 days of increased training and recovery in cyclists.	2002-11	12439775
Pubertal and gender-related changes in the sympathoadrenal system in healthy children.	2002-11	12414869
Effects of slow-release octreotide on urinary metanephrine excretion and plasma chromogranin A and catecholamine levels in patients with malignant or recurrent phaeochromocytoma.	2002-11	12390337
Upper reference limits for urinary catecholamines, metanephrines and 3-methoxy-4-hydroxymandelic acid in hypertensive patients.	2002-10	12476950
Pheochromocytoma: a disease with many faces.	2002-10	12389350
[Diagnostic and therapeutic strategy for an incidental finding of an adrenal mass].	2002-09	12410136

Patents

Sample Use Guides

In Vivo Use Guide

Dogs were treated with metanephrine i.v. at a rate of 50mkg/kg/min for a 10-min period and then at a rate of 20mkg/kg/min for

Route of Administration: Intravenous

In Vitro Use Guide

Caki-1 cells were preincubated at 37°C for 20 min in buffer A (125 mM NaCl, 4.8 mM KCl, 1.2 mM CaCl2, 1.2 mM KH2PO4, 1.2 mM MgSO4, 25 mM HEPES, 5.6 mM D-(+)-glucose, 1 mM L-(+)-ascorbic acid; pH 7.4). Subsequently, cells were incubated at 37°C with 300 μl buffer A containing 200 nM [3H]MPP+. Incubation was stopped by rinsing the cells with 300 μl ice-cold buffer A. The cells were then solubilized with 0.1% (v/v) Triton X-100 (in 5 mM Tris-HCl, pH 7.4), and placed at 37°C overnight. When used, inhibitors of transport (Metanephrine) were present during both the preincubation and incubation periods. Radioactivity was measured by liquid scintillation counting.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 23:33:21 GMT 2025` Edited by `admin` on `Mon Mar 31 23:33:21 GMT 2025`
Record UNII	1ZE0530JEJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METANEPHRINE, (+/-)

Common Name

English

(±)-METANEPHRINE

Preferred Name

English

METANEPHRINE [MI]

Common Name

English

DL-3-O-METHYLADRENALINE

Common Name

English

M-O-METHYLADRENALINE

Common Name

English

METADRENALINE

Common Name

English

BENZENEMETHANOL, 4-HYDROXY-3-METHOXY-.ALPHA.-((METHYLAMINO)METHYL)-

Systematic Name

English

DL-METANEPHRINE

Common Name

English

4-HYDROXY-3-METHOXY-.ALPHA.-(METHYLAMINOMETHYL)BENZENEMETHANOL

Systematic Name

English

METANEPHRINE, (±)-

Common Name

English

3-METHOXYADRENALINE

Systematic Name

English

Classification Tree Code System Code

LOINC

21019-5