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SML0712

Sigma-Aldrich

1-Methyl-1,2,3,4-tetrahydroisoquinoline

≥97% (GC)

Sinónimos:

1,2,3,4-Tetrahydro-1-methylisoquinoline, 1MeTIQ

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About This Item

Fórmula empírica (notación de Hill):
C10H13N
Número de CAS:
4965-09-7
Peso molecular:
147.22
UNSPSC Code:
12352200
NACRES:
NA.77

assay

≥97% (GC)

form

oil

color

, colorless to light yellow to light pink

storage temp.

2-8°C

InChI

1S/C10H13N/c1-8-10-5-3-2-4-9(10)6-7-11-8/h2-5,8,11H,6-7H2,1H3

InChI key

QPILYVQSKNWRDD-UHFFFAOYSA-N

Biochem/physiol Actions

1-Methyl-1,2,3,4-tetrahydroisoquinoline (1MeTIQ) is an endogenous antidepressant and parkinsonism-preventing substance that demonstrates neuroprotectiveactivity. Following systemic administration in rats, 1-Methyl-1,2,3,4-tetrahydroisoquinoline produces antidepressant-like effect similar to the effect of imipramine. 1MeTIQ is a reversible short-acting moderate inhibitor of MAO A/B.

Features and Benefits

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

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

13 - Non Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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K Ishiwata et al.
Journal of neurochemistry, 79(4), 868-876 (2001-11-28)
Parkinsonism-inducing neurotoxicity of 1,2,3,4-tetrahydroisoquinoline (TIQ), as contrasted to 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP), and parkinsonism-preventing effect of 1-methyl-1,2,3,4-tetrahydroisoquinoline (1-MeTIQ) have been investigated in mice by measuring their effects on the in vivo binding of radioligand to pre-synaptic dopamine transporters (DATs) or to dopamine
Lucyna Antkiewicz-Michaluk et al.
European journal of pharmacology, 466(3), 263-269 (2003-04-16)
The effect of single and multiple administration of the neurotoxic pesticide, rotenone, and the potentially neuroprotective compound, 1-methyl-1,2,3,4-tetrahydroisoquinoline (1MeTIQ), on the concentration of dopamine and its metabolites (homovanillic acid-HVA, 3,4-dihydroxyphenylacetic acid-DOPAC, and 3-methoxytyramine-3-MT)) in three brain areas was studied by
Yoshie Horiguchi et al.
Chemical & pharmaceutical bulletin, 52(2), 214-220 (2004-02-06)
The sulfoxides 7b and 7d carrying thiophene or benzothiophene as heteroaromatic nucleophiles, when treated with trifluoroacetic anhydride at room temperature (Pummerer reaction), underwent an intramolecular alkylation in an exclusive manner to yield 4,5,6,7-tetrahydro-7-methyl-4-phenylsulfanylthieno[2,3-c]pyridine-6-carbaldehyde (10) and the corresponding benzothiophene derivative (12b)
Lucyna Antkiewicz-Michaluk et al.
The international journal of neuropsychopharmacology, 7(2), 155-163 (2004-01-27)
The aim of this paper was to investigate whether rotenone, a pesticide causing experimental parkinsonism, causes direct damage to dopaminergic structure when injected intracerebrally and whether this action may be prevented by peripheral administration of 1-methyl-1,2,3,4-tetrahydroisoquinoline (1MeTIQ), an endogenous compound
Jarogniew J Luszczki et al.
Neuropharmacology, 50(2), 133-142 (2005-09-13)
1-Methyl-1,2,3,4-tetrahydroisoquinoline (1-MeTHIQ - an endogenous parkinsonism-preventing substance) administered intraperitoneally at a dose of 20 mg/kg considerably elevated the threshold for electroconvulsions in mice from 6.4 to 8.4 mA (P < 0.05). In contrast, the agent administered at 5 and 10
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