Skip to Content
Merck
All Photos(1)

Key Documents

View All Documentation

Safety Information

SML0399

Sigma-Aldrich

D,L-Metanephrine hydrochloride

≥98% (HPLC)

Synonym(s):

(±)-Metanephrine hydrochloride, 4-Hydroxy-3-methoxy-a-[(methylamino)methyl]-benzenemethanol hydrochloride, DL-3-O-Methyladrenaline hydrochloride, DL-Metanephrine hydrochloride, Metadrenaline hydrochloride, dl-Metanephrine hydrochloride, m-O-Methyladrenaline hydrochloride

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C10H15NO3 · HCl
CAS Number:
881-95-8
Molecular Weight:
233.69
EC Number:
212-922-2
MDL number:
MFCD00012487
UNSPSC Code:
12352200
PubChem Substance ID:
329825395
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

powder

storage condition

desiccated

color

white to beige

solubility

H2O: 12 mg/mL (clear solution)

storage temp.

2-8°C

SMILES string

OC1=C(OC)C=C(C(CNC)O)C=C1.Cl

InChI

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

InChI key

HRIQFVCFOPJYEQ-UHFFFAOYSA-N

Biochem/physiol Actions

Metanephrine is an endogenous metabolite of ephinephrine, formed by catechol-O-methyl transferase activity. It is best known as a biomarker for cancers, as levels of free metanephrine are used to diagnose pheochromocytoma. Metanephrine was previously thought to be biologically inactive, but it is a more potent agonist at Trace amine associated receptor TAAR1 than either epinephrine or norepinephrine. Trace amine associated receptors (TAARs) are recently discovered GPCRs that are activated by endogenous trace amines (tyramine, tryptamine, synephrine, octopamine, β-phenylethylamine), which are chemically similar to monoaminergic neurotransmitters (epinephrine, norepinephrine, dopamine). Trace amines and TAARs are expressed in brain and are implicated in modulation of monoaminergic neurotransmission.

Features and Benefits

This compound is featured on the Dopamine and Norepinephrine Metabolism page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

SML0399-10MG:
SML0399-BULK:
SML0399-VAR:
SML0399-IP:
SML0399-50MG:

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Augusto Q Pedro et al.
Microbial cell factories, 14, 113-113 (2015-08-08)
Membrane proteins are important drug targets in many human diseases and gathering structural information regarding these proteins encourages the pharmaceutical industry to develop new molecules using structure-based drug design studies. Specifically, membrane-bound catechol-O-methyltransferase (MBCOMT) is an integral membrane protein that

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service