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M1641

Sigma-Aldrich

Methoxyphenamine hydrochloride

≥99%

Synonym(s):

2-Methoxy-N,α-dimethylbenzeneethanamine hydrochloride, NSC 65644

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About This Item

Empirical Formula (Hill Notation):
C11H17NO · HCl
CAS Number:
5588-10-3
Molecular Weight:
215.72
EC Number:
226-993-2
MDL number:
MFCD00034832
UNSPSC Code:
12352100
PubChem Substance ID:
57654358
NACRES:
NA.22

Assay

≥99%

drug control

regulated under CDSA - not available from Sigma-Aldrich Canada

SMILES string

Cl.CNC(C)Cc1ccccc1OC

InChI

1S/C11H17NO.ClH/c1-9(12-2)8-10-6-4-5-7-11(10)13-3;/h4-7,9,12H,8H2,1-3H3;1H

InChI key

FGSJNNQVSUVTPW-UHFFFAOYSA-N

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Mario Thevis et al.
European journal of mass spectrometry (Chichester, England), 14(3), 145-152 (2008-08-19)
Methoxyphenamine (o-methoxy-N,alpha-dimethylphenethylamine, Orthoxine) used in earlier times as a bronchodilator is prohibited in sports according to the regulations of the World Anti-Doping Agency (WADA). The drug and several of its metabolites are commonly analysed in doping control screening assays using
W A Lau et al.
British journal of pharmacology, 101(2), 394-398 (1990-10-01)
1. Nasal resistance in anaesthetized rats was assessed by measuring air overflow during ventilation of the nasal passages at constant pressure. Nasal basal resistance was reduced in a dose-dependent manner by methoxyphenamine hydrochloride (0.01-30 mg kg-1, i.v.), pseudoephedrine hydrochloride (0.03-3
G Muralidharan et al.
Xenobiotica; the fate of foreign compounds in biological systems, 19(2), 189-197 (1989-02-01)
1. Lewis and Dark Agouti (DA) rat strains (n = 4), models of human extensive and poor metabolizer phenotypes of debrisoquine/sparteine, respectively, were dosed with methoxyphenamine with and without prior administration of quinidine. Methoxyphenamine and its three metabolites, namely N-desmethylmethoxyphenamine
S D Roy
Xenobiotica; the fate of foreign compounds in biological systems, 20(1), 55-70 (1990-01-01)
1. Methoxyphenamine (MP) was metabolized in vitro by rat liver preparations to O-desmethylmethoxyphenamine (O-desmethyl-MP), N-desmethylmethoxyphenamine (N-desmethyl-MP) and 5-hydroxymethoxyphenamine (5-hydroxy-MP). These metabolic pathways were inhibited by SKF 525-A and carbon monoxide, which indicates that these reactions were mediated at least partly
R T Coutts et al.
Drug metabolism and disposition: the biological fate of chemicals, 22(5), 756-760 (1994-09-01)
Metabolism of methoxyphenamine (MP) was conducted in vitro using commercially available microsomes prepared from human AHH-1 TK+/-cells in which CYP2D6 had been expressed. This study has confirmed the involvement of CYP2D6 in the metabolism of MP to O-desmethylmethoxyphenamine (ODMP) and
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