Details
Stereochemistry | RACEMIC |
Molecular Formula | C10H13NO2.ClH |
Molecular Weight | 215.677 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CC1NCCC2=C1C=C(O)C(O)=C2
InChI
InChIKey=WSVCGYSRZYNJMC-UHFFFAOYSA-N
InChI=1S/C10H13NO2.ClH/c1-6-8-5-10(13)9(12)4-7(8)2-3-11-6;/h4-6,11-13H,2-3H2,1H3;1H
Molecular Formula | ClH |
Molecular Weight | 36.461 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C10H13NO2 |
Molecular Weight | 179.2157 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Salsolinol (1-methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline, SAL) is a tetrahydroisoquinoline derivative, detected in humans. Salsolinol can be formed in the mammalian brain by three different mechanisms: (1) via the nonenzymatic Pictet–Spengler condensation of dopamine and aldehydes producing salsolinol as two racemic isomers (R or S). (2) By the nonenzymatic condensation of dopamine and pyruvate yielding 1-carboxyl-tetrahydroisoquinoline, followed by decarboxylation and reduction, which produces (R)-salsolinol. (3) By selective synthesis of (R)-salsolinol from dopamine and acetaldehyde, the level of which is increased after ethanol intake. Apart from that salsolinol has also been detected in certain beverages and foodstuff, including soy sauce, cheese. Only the (R) enantiomer of Salsolinol and occur in the human brain, cerebrospinal fluid (CSF) and intraventricular fluid (IVF), and the (S) enantiomer was not detected. Salsolinol was also found to be involved in neurotoxicity processes altering the normal function and survival of dopamine neurons. It has been proposed, that salsolinol participated in the etiopathogenesis of Parkinson’s disease. Salsolinol could inhibit various enzymes, for example, monoamine oxidase and tyrosine hydroxylase and recently was revealed, that (R)-SAL and (S)-SAL were agonists of the μ-opioid receptor. (S)-SAL is a more potent agonist than the (R)-SAL stereoisomer, it was suggested that an opioid action of SAL or its enantiomers is involved in the rewarding effects of ethanol.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P35372|||G8XRH8|||Q5TDA1|||Q9UN57 Gene ID: 4988.0 Gene Symbol: OPRM1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/28167903 |
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Target ID: P07101|||Q2M3B4 Gene ID: 7054.0 Gene Symbol: TH Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/1349343 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Diagnostic | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Biomarkers in Parkinson's disease (recent update). | 2013 Sep |
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Salsolinol, an endogenous compound triggers a two-phase opposing action in the central nervous system. | 2015 Apr |
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Chronic salsolinol administration prevents the behavioral and neurochemical effects of L-DOPA in rats. | 2015 May |
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Racemic Salsolinol and its Enantiomers Act as Agonists of the μ-Opioid Receptor by Activating the Gi Protein-Adenylate Cyclase Pathway. | 2016 |
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Mystic Acetaldehyde: The Never-Ending Story on Alcoholism. | 2017 |
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Involvement of salsolinol in the suckling-induced oxytocin surge in sheep. | 2017 Apr |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25711629
in rats: there was investigated the impact of acute and chronic salsolinol (100 mg.kg i.p.) administration on L-DOPA-induced locomotor hyperactivity and neurochemical changes
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25537852
It was evaluated the effect of different (50, 100, and 500 µM) concentrations of salsolinol on markers of glutamate-induced apoptotic and neurotoxic cell damage, such as caspase-3 activity, lactate dehydrogenase (LDH) release, and the loss of mitochondrial membrane potential. Salsolinol had biphasic effects, namely, at lower concentrations (50 and 100 µM), it demonstrated a distinct neuroprotective activity, whereas in the highest one (500 µM) caused neurotoxic effect. Salsolinol in concentrations of 50 and 100 µM significantly antagonized the pro-apoptotic and neurotoxic effects caused by 1 mM glutamate. Salsolinol diminished the number of bright fragmented nuclei with condensed chromatin and increased cell survival in Hoechst 33342 and calcein AM staining in hippocampal cultures. Additionally, in the low 50 µM concentration, it produced a significant inhibition of glutamate-induced loss of membrane mitochondrial potential. Only the highest concentration of salsolinol (500 µM) enhanced the glutamate excitotoxicity.
Substance Class |
Chemical
Created
by
admin
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Edited
Fri Dec 15 17:49:16 GMT 2023
by
admin
on
Fri Dec 15 17:49:16 GMT 2023
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Record UNII |
1C0F27WEAL
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Record Status |
Validated (UNII)
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Record Version |
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE |