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SML0398

Sigma-Aldrich

Salsolinol hydrobromide

≥96% (HPLC)

Synonym(s):

(R,S)-Salsolinol hydrobromide, 1,2,3,4-Tetrahydro-1-methylisoquinoline-6,7-diol hydrobromide, 1-Methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol hydrobromide, 1-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline 1,2,3,4-Tetrahydro-1-methylisoquinoline-6,7-diol hydrobromide; 1-Methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol hydrobromide;

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About This Item

Empirical Formula (Hill Notation):
C10H13NO2 · HBr
CAS Number:
59709-57-8
Molecular Weight:
260.13
MDL number:
MFCD00012741
UNSPSC Code:
51111800
PubChem Substance ID:
329825394
NACRES:
NA.77

assay

≥96% (HPLC)

form

powder

storage condition

desiccated

color

white to brown

solubility

H2O: 5 mg/mL (warmed; clear solution)

storage temp.

2-8°C

SMILES string

Br.CC1NCCc2cc(O)c(O)cc12

InChI

1S/C10H13NO2.BrH/c1-6-8-5-10(13)9(12)4-7(8)2-3-11-6;/h4-6,11-13H,2-3H2,1H3;1H

InChI key

OGMGXKJQIOUTTB-UHFFFAOYSA-N

General description

Salsolinol (6,7-dihydroxy-1-methyl-1,2,3,4-tetrahydroisoquinoline) is present in various edibles. It is available as R and S enantiomers. R-salsolinol in predominantly found in the brain tissue of humans.

Biochem/physiol Actions

Salsolinol is the condensation product of acetaldehyde and dopamine. Salsolinol is a potential neurotoxin suspected to contribute to alcohol abuse. It appears that salsolinol excites the ventral tegmental area (VTA) dopamine neurons indirectly by activating μ-opioid receptors (MORs), which inhibit GABA neurons in the VTA.
Salsolinol, a neurotoxin, can serve as a prolactin-releasing factor and an etiological factor in the tuberoinfundibular pathway and in Parkinson′s disease (PD), respectively. It can also act as a modulator of catecholaminergic neurotransmission in the nigrostriatal pathway. In central nervous system, salsolinol can change the role of dopaminergic neurons and dopamine metabolism.

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

signalword

Warning

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - 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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Magdalena Kurnik-Łucka et al.
Neurotoxicity research, 37(2), 286-297 (2019-11-17)
Salsolinol (6,7-dihydroxy-1-methyl-1,2,3,4-tetrahydroisoquinoline), widely available in many edibles, is considered to alter the function of dopaminergic neurons in the central nervous system and thus, multiple hypotheses on its either physiological and/or pathophysiological role have emerged. The aim of our work was
Adriana Prado et al.
Journal of applied toxicology : JAT, 35(2), 219-227 (2014-05-24)
Unforeseen toxic effects contribute to compound attrition during preclinical evaluation and clinical trials. Consequently, there is a need to correlate in vitro toxicity to in vivo and clinical outcomes quickly and effectively. We propose an expedited evaluation of physiological parameters

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