NORMETANEPHRINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C9H13NO3
Molecular Weight	183.2044
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC(=CC=C1O)C(O)CN

InChI

InChIKey=YNYAYWLBAHXHLL-UHFFFAOYSA-N

InChI=1S/C9H13NO3/c1-13-9-4-6(8(12)5-10)2-3-7(9)11/h2-4,8,11-12H,5,10H2,1H3

HIDE SMILES / InChI

Molecular Formula	C9H13NO3
Molecular Weight	183.2044
Charge	0
Count

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

Approval Year

PubMed

Title	Date	PubMed
Measurement of urinary metanephrines to screen for pheochromocytoma in an unselected hospital referral population.	2006-11	16990424
The role of chromogranin A in the management of patients with phaeochromocytoma.	2006-09	16918946
Phaeochromocytoma in pregnancy.	2006-09	16911553
Cortisol production rate in posttraumatic stress disorder.	2006-09	16787989
Pretreatment and one-shot separating analysis of whole catecholamine metabolites in plasma by using LC/MS.	2006-07	16791560
A case of sleep apnea syndrome manifesting severe hypertension with high plasma norepinephrine levels.	2006-06	16717398
Absence of exercise-induced leptin suppression associated with insufficient epinephrine reserve in patients with classic congenital adrenal hyperplasia due to 21-hydroxylase deficiency.	2006-03	16636975
[Diffuse uptake of brown fat on computed-tomography coupled positron emission tomoscintigraphy (PET-CT) for the exploration of extra-adrenal pheochromocytoma].	2006-03	16596052
Diagnostic value of various biochemical parameters for the diagnosis of pheochromocytoma in patients with adrenal mass.	2006-03	16498054
Low catechol-O-methyltransferase activity in the brain and blood pressure regulation.	2006-02	16462018
Paradoxical decrease in blood pressure after relief of cardiac tamponade: the role of sympathetic activity.	2006-02	16449957
Mutation analysis of SDHB and SDHC: novel germline mutations in sporadic head and neck paraganglioma and familial paraganglioma and/or pheochromocytoma.	2006-01-11	16405730
Detecting pheochromocytoma: defining the most sensitive test.	2006-01	16371743
A dopaminergic deficit hypothesis of schizophrenia: the path to discovery.	2006	16640125
Age-related differences in hormonal and nutritional impact on lean anorexia nervosa bone turnover uncoupling.	2006	16541206
[Metanephrine (M), normetanephrine (NM) and fractionated metanephrines].	2005-08	16149538
Effect of oral administration of zanapezil (TAK-147) for 21 days on acetylcholine and monoamines levels in the ventral hippocampus of freely moving rats.	2005-08	15951830
Cyclooxygenase-1-deficient mice have high sleep-to-wake blood pressure ratios and renal vasoconstriction.	2005-06	15883230
Improved assay for catechol-O-methyltransferase activity utilizing norepinephrine as an enzymatic substrate and reversed-phase high-performance liquid chromatography with fluorescence detection.	2005-05-13	15941038
Rapid assay for catechol-O-methyltransferase activity by high-performance liquid chromatography-fluorescence detection.	2005-05-05	15797519
Training of elite cyclists: effects on mood state and selected hormonal responses.	2005-04-02	15801496
Pheochromocytoma catecholamine phenotypes and prediction of tumor size and location by use of plasma free metanephrines.	2005-04	15718487
Biochemical and clinical manifestations of dopamine-producing paragangliomas: utility of plasma methoxytyramine.	2005-04	15644397
Long-term morphological and hormonal follow-up in a single unit on 115 patients with adrenal incidentalomas.	2005-03-28	15770213
The use of plasma metanephrine to normetanephrine ratio to determine epinephrine poisoning.	2005-03	15698588
Expression of human dopamine receptor in potato (Solanum tuberosum) results in altered tuber carbon metabolism.	2005-02-09	15701180
Precisely wrong? Urinary fractionated metanephrines and peer-based laboratory proficiency testing.	2005-02	15681566
Plasma metanephrines in renal failure.	2005-02	15673315
Biochemical diagnosis, localization and management of pheochromocytoma: focus on multiple endocrine neoplasia type 2 in relation to other hereditary syndromes and sporadic forms of the tumour.	2005-01	15606377
Pheochromocytoma presenting as heart failure.	2005	16030412
Decomposition of protonated noradrenaline and normetanephrine assisted by NH2 migration studied by electrospray tandem mass spectrometry and molecular orbital calculations.	2005	15712294
Nonparametric determination of reference intervals for plasma metanephrine and normetanephrine.	2004-12	15563487
Assessment of O-methylated catecholamine levels in plasma and urine for diagnosis of autonomic disorders.	2004-11-30	15556832
Laparoscopic adrenalectomy for isolated adrenal metastasis.	2004-11-24	15554272
Extraneuronal enzymatic degradation of myocardial interstitial norepinephrine in the ischemic region.	2004-10-01	15364620
Malignant pheochromocytoma associated with germline mutation of the SDHB gene.	2004-10	15371856
Paracetamol-associated interference in an HPLC-ECD assay for urinary free metadrenalines and catecholamines.	2004-07	15298744
Changes in c-fos expression in the rat heart during morphine withdrawal. Involvement of alpha2-adrenoceptors.	2004-07	15249992
Predictive value of preoperative transthoracic echocardiography in patients undergoing adrenalectomy for pheochromocytoma.	2004-07	15196103
Experience with surgical excision in childhood pheochromocytoma.	2004-06	15201507
The economic implications of three biochemical screening algorithms for pheochromocytoma.	2004-06	15181069
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
Toward a rapidly acting antidepressant: the normetanephrine and extraneuronal monoamine transporter (uptake 2) hypothesis.	2004-05	15121658
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
The catecholamine biosynthesis route in potato is affected by stress.	2004-04-16	15331087
Measurement of plasma free metanephrine and normetanephrine by liquid chromatography-tandem mass spectrometry for diagnosis of pheochromocytoma.	2004-03	14726465
Laparoscopic management of extra-adrenal pheochromocytoma.	2004-01	14665847
Alterations of brain tissue in fetal rats exposed to nicotine in utero: possible involvement of nitric oxide and catecholamines.	2002-12-03	15001219

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:35:41 GMT 2025` Edited by `admin` on `Mon Mar 31 17:35:41 GMT 2025`
Record UNII	0J45DE6B88
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NORMETANEPHRINE

Common Name

English

(±)-NORMETANEPHRINE

Preferred Name

English

3-METHOXYNORADRENALINE

Common Name

English

NORMETANEPHRINE [MI]

Common Name

English

3-O-METHYLNORADRENALINE

Common Name

English

NORMETANEPHRINE, (±)-

Common Name

English

3-METHOXYNOREPINEPHRINE

Common Name

English

VANILLYL ALCOHOL, .ALPHA.-(AMINOMETHYL)-

Common Name

English

3-METHOXY-4-HYDROXYPHENYLETHANOLAMINE

Systematic Name

English

DL-3-O-METHYLNOREPINEPHRINE

Common Name

English

3-O-METHYLNOREPINEPHRINE

Common Name

English

DL-NORMETANEPHRINE

Common Name

English

DL-M-O-METHYLNOREPINEPHRINE

Common Name

English

3-O-METHYLARTERENOL

Common Name

English

4-HYDROXY-3-METHOXY-.ALPHA.-(AMINOMETHYL)BENZYL ALCOHOL

Systematic Name

English

.ALPHA.-(AMINOMETHYL)VANILLYL ALCOHOL

Common Name

English

.ALPHA.-(AMINOMETHYL)-4-HYDROXY-3-METHOXYBENZENEMETHANOL

Systematic Name

English

4-HYDROXY-3-METHOXYPHENETHANOLAMINE

Common Name

English

4-(2-AMINO-1-HYDROXYETHYL)-2-METHOXYPHENOL

Systematic Name

English

3-METHOXY-4,.BETA.-DIHYDROXYPHENYLETHYLAMINE

Systematic Name

English

Classification Tree Code System Code

LOINC

2669-0