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Details

Stereochemistry RACEMIC
Molecular Formula C10H15NO3
Molecular Weight 197.2314
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METANEPHRINE

SMILES

CNCC(c1ccc(c(c1)OC)O)O

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 197.2314
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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

Curator's Comment:: Known to be CNS penetrant in Anguilla anguilla L.. Human data not available

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
34.2 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
Diagnostic
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Pheochromocytoma.
2001 Aug
How to detect pheochromocytomas?--the diagnostic relevance of plasma free metanephrines.
2002 Apr 15
Serum chromogranin-alpha immunoradiometric assay in the diagnosis of pheochromocytoma.
2002 Apr-Jun
Sequential ACTH and catecholamine secretion in a phaeochromocytoma.
2002 Aug
Preparation and characterization of immunogens for antibody production against metanephrine and normetanephrine.
2002 Aug 1
Twelve-year experience in the investigation and treatment of paragangliomas.
2002 Dec
NIH state-of-the-science statement on management of the clinically inapparent adrenal mass ("incidentaloma").
2002 Feb 4-6
Adrenomedullary function may predict phenotype and genotype in classic 21-hydroxylase deficiency.
2002 Jul
Imaging vs biochemical testing for pheochromocytoma.
2002 Jul 17
Cardiovascular abnormalities in patients with a carcinoid syndrome.
2002 Mar
Phaeochromocytoma with normal urinary catecholamines: the potential value of urinary free metadrenalines.
2002 Nov
Psychobiologic responses to 4 days of increased training and recovery in cyclists.
2002 Nov
Pubertal and gender-related changes in the sympathoadrenal system in healthy children.
2002 Nov
Upper reference limits for urinary catecholamines, metanephrines and 3-methoxy-4-hydroxymandelic acid in hypertensive patients.
2002 Oct
[Diagnostic and therapeutic strategy for an incidental finding of an adrenal mass].
2002 Sep
Determination of catecholamines and metanephrines in urine by capillary electrophoresis-electrospray ionization-time-of-flight mass spectrometry.
2002 Sep 5
Effects of Qigong on blood pressure, blood pressure determinants and ventilatory function in middle-aged patients with essential hypertension.
2003
Adrenal cortical phaeochromocytoma: a case report of a rare entity.
2003 Apr
Catecholamines increase in the urine of non-segmental vitiligo especially during its active phase.
2003 Apr
Plasma levels of catechols and metanephrines in neurogenic orthostatic hypotension.
2003 Apr 22
A pitfall of metaiodobenzylguanidine scan: paraganglioma in close proximity to adrenocortical adenoma.
2003 Aug
Pheochromocytoma: state-of-the-art and future prospects.
2003 Aug
Pheochromocytoma: rediscovery as a catecholamine-metabolizing tumor.
2003 Fall
A comparison of biochemical tests for pheochromocytoma: measurement of fractionated plasma metanephrines compared with the combination of 24-hour urinary metanephrines and catecholamines.
2003 Feb
Editorial: biochemical diagnosis of pheochromocytoma--is it time to switch to plasma-free metanephrines?
2003 Feb
Kinetic inhibitory profile of BIA 3-202, a novel fast tight-binding, reversible and competitive catechol-O-methyltransferase inhibitor.
2003 Jan 24
Microemulsion electrokinetic chromatographic analysis of some polar compounds.
2003 Jan 5
Prolonged survival of a patient with multiple endocrine neoplasia type 2b and stage IV medullary thyroid carcinoma.
2003 Jan-Feb
Exercise induces excessive normetanephrine responses in hypertensive diabetic patients.
2003 Jun
Screening for endogenous substrates reveals that CYP2D6 is a 5-methoxyindolethylamine O-demethylase.
2003 Jun
Sources and significance of plasma levels of catechols and their metabolites in humans.
2003 Jun
[Current management of pheochromocytoma: about 50 cases].
2003 May
Stability of plasma free metanephrines during collection and storage as assessed by an optimized HPLC method with electrochemical detection.
2003 Nov
Phaeochromocytoma unmasked by drug therapy.
2003 Oct
Diabetes as a marker of pheochromocytoma in hypertensive patients.
2003 Sep
Chiral on-chip separations of neurotransmitters.
2003 Sep 1
In vivo assessment of catechol O-methyltransferase activity in rabbit skeletal muscle.
2004 Apr 30
Paracetamol-associated interference in an HPLC-ECD assay for urinary free metadrenalines and catecholamines.
2004 Jul
Does iodine-131 meta-iodobenzylguanidine (MIBG) scintigraphy have an impact on the management of sporadic and familial phaeochromocytoma?
2004 Jul
Predictive value of preoperative transthoracic echocardiography in patients undergoing adrenalectomy for pheochromocytoma.
2004 Jul
[Adrenal incidentaloma associated to elevated urinary normethanephrine in a patient with high blood pressure].
2004 Jul-Aug
Development of enantioselective immunoassays for free plasma metanephrines.
2004 Jun
Experience with surgical excision in childhood pheochromocytoma.
2004 Jun
The economic implications of three biochemical screening algorithms for pheochromocytoma.
2004 Jun
Pitfall in HPLC assay for urinary metanephrines: an unusual type of interference caused by methenamine intake.
2004 Jun
[Hypertension secondary to pheochromocytoma].
2004 Mar
Contactless conductivity detection of selected organic ions in on-chip electrophoresis.
2004 Mar
Measurement of plasma free metanephrine and normetanephrine by liquid chromatography-tandem mass spectrometry for diagnosis of pheochromocytoma.
2004 Mar
Hormonal changes during long-term isolation.
2004 May
The significance of cystic adrenal lesions in multiple endocrine neoplasia IIB syndrome.
2004 Oct
Patents

Sample Use Guides

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
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 Sat Jun 26 10:02:33 UTC 2021
Edited
by admin
on Sat Jun 26 10:02:33 UTC 2021
Record UNII
1ZE0530JEJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METANEPHRINE
MI  
Common Name English
METANEPHRINE [MI]
Common Name English
(+/-)-METANEPHRINE
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
Created by admin on Sat Jun 26 10:02:33 UTC 2021 , Edited by admin on Sat Jun 26 10:02:33 UTC 2021
LOINC 44337-4
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LOINC 29141-9
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LOINC 35644-4
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LOINC 14831-2
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LOINC 22757-9
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LOINC 25955-6
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LOINC 47699-4
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NCI_THESAURUS C88516
Created by admin on Sat Jun 26 10:02:33 UTC 2021 , Edited by admin on Sat Jun 26 10:02:33 UTC 2021
LOINC 25473-0
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LOINC 34339-2
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LOINC 11139-3
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LOINC 9645-3
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LOINC 19049-6
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LOINC 11140-1
Created by admin on Sat Jun 26 10:02:33 UTC 2021 , Edited by admin on Sat Jun 26 10:02:33 UTC 2021
Code System Code Type Description
PUBCHEM
21100
Created by admin on Sat Jun 26 10:02:33 UTC 2021 , Edited by admin on Sat Jun 26 10:02:33 UTC 2021
PRIMARY
MERCK INDEX
M7267
Created by admin on Sat Jun 26 10:02:33 UTC 2021 , Edited by admin on Sat Jun 26 10:02:33 UTC 2021
PRIMARY Merck Index
FDA UNII
1ZE0530JEJ
Created by admin on Sat Jun 26 10:02:33 UTC 2021 , Edited by admin on Sat Jun 26 10:02:33 UTC 2021
PRIMARY
CAS
5001-33-2
Created by admin on Sat Jun 26 10:02:33 UTC 2021 , Edited by admin on Sat Jun 26 10:02:33 UTC 2021
PRIMARY
NCI_THESAURUS
C107556
Created by admin on Sat Jun 26 10:02:33 UTC 2021 , Edited by admin on Sat Jun 26 10:02:33 UTC 2021
PRIMARY NCIT
WIKIPEDIA
Metanephrine
Created by admin on Sat Jun 26 10:02:33 UTC 2021 , Edited by admin on Sat Jun 26 10:02:33 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> METABOLITE