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SML0712

Sigma-Aldrich

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

≥97% (GC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C10H13N
CAS Number:
4965-09-7
Molecular Weight:
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

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’.

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M Filip et al.
Journal of physiology and pharmacology : an official journal of the Polish Physiological Society, 58(4), 625-639 (2008-01-16)
The efficacy of 1-methyl-1,2,3,4-tetrahydroisoquinoline (1MeTIQ), a member of endogenous tetrahydroisoquinolines, in cocaine- and food-maintained responding in self-administration procedures under a fixed ratio 5 schedule of reinforcement as well as in cocaine and food seeking behaviors in male Wistar rats was
L Antkiewicz-Michaluk et al.
Journal of neural transmission (Vienna, Austria : 1996), 114(3), 307-317 (2006-08-10)
Drug abuse disorder is induced by a variety of substances and results from their interaction with the brain reward system. It is characterized by a high frequency of relapse, usually associated with to craving. In this study we investigated the
Elhadi Absi et al.
Brain research, 955(1-2), 161-163 (2002-11-07)
1-Methyl-1,2,3,4-tetrahydroisoquinoline (1-MeTIQ), an endogenous monoamine, which prevents the neurotoxic effect of 1-methyl-4-phenylpyridinium ion (MPP(+)) and other endogenous neurotoxins, has been described as being enzymatically formed in the brain by the 1-MeTIQ synthesizing enzyme (1-MeTIQse). In this paper, we report the
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
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)
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