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209848

Sigma-Aldrich

α-(Methylaminomethyl)benzyl alcohol

99%

Synonym(s):

Halostachine

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About This Item

Linear Formula:
C6H5CH(CH2NHCH3)OH
CAS Number:
Molecular Weight:
151.21
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22

assay

99%

form

solid

mp

74-76 °C (lit.)

functional group

amine
hydroxyl
phenyl

SMILES string

CNCC(O)c1ccccc1

InChI

1S/C9H13NO/c1-10-7-9(11)8-5-3-2-4-6-8/h2-6,9-11H,7H2,1H3

InChI key

ZCTYHONEGJTYQV-UHFFFAOYSA-N

General description

α-(Methylaminomethyl)benzyl alcohol is a potential substrate for studies involving phenylethanolamine-N-methyltransferase.

Application

α-(Methylaminomethyl)benzyl alcohol was used in the synthesis of 1,4-disubstituted-2,3,4,5-tetrahydro-1H-3-benzazepines. It was also used as internal standard during determination of pseudoephedrine and phenylpropanolamine urine concentrations by HPLC.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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S W Gerritz et al.
Organic letters, 2(25), 4099-4102 (2000-12-12)
[structure] Two general routes to 1,4-disubstituted-2,3,4, 5-tetrahydro-1H-3-benzazepines are described. Both routes utilize an appropriately functionalized phenethylamino alcohol as the penultimate intermediate: the first route makes use of the reductive amination of a benzyl alkyl ketone with alpha-(aminomethyl)benzyl alcohol, while the
O Inoue et al.
Progress in neuro-psychopharmacology & biological psychiatry, 8(3), 385-395 (1984-01-01)
The radiotracers, C-14-N-methylphenylethylamine (MPEA) and N-methylphenylethanolamine (MPEOA) both rapidly entered mouse brain after their intravenous injection and were metabolized by brain monoamine oxidase (MAO) to C-14-methylamine and corresponding aldehydes. The labelled metabolite was trapped in the brain. Measurement of radioactivity
Neil Chester et al.
British journal of clinical pharmacology, 57(1), 62-67 (2003-12-18)
To study the elimination of ephedrines with reference to the International Olympic Committee (IOC) doping control cut-off levels, following multiple dosing of over-the-counter decongestant preparations. A double-blind study was performed in which 16 healthy male volunteers were administered either pseudoephedrine
The vasoactive potential of halostachine, an alkaloid of tall fescue (Festuca arundinaceae, Schreb) in cattle.
C B Davis et al.
Veterinary and human toxicology, 25(6), 408-411 (1983-12-01)
H E Shannon et al.
The Journal of pharmacology and experimental therapeutics, 217(2), 379-385 (1981-05-01)
Single i.v. doses of the endogenous trace amine phenylethanolamine (PEOH) and its N-methyl homolog (NMPEOH) were administered to separate groups of five dogs. The dose- and time-related effects of these compounds were measured on pupillary diameter, heart rate and body

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