Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C12H17NO2 |
Molecular Weight | 207.2689 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC2=C(C=C1OC)[C@H](C)NCC2
InChI
InChIKey=HMYJLVDKPJHJCF-QMMMGPOBSA-N
InChI=1S/C12H17NO2/c1-8-10-7-12(15-3)11(14-2)6-9(10)4-5-13-8/h6-8,13H,4-5H2,1-3H3/t8-/m0/s1
Salsolidine is a simple 1-substituted tetrahydroisoquinoline isolated from many natural sources as the racemate and in its enantiomeric modifications. Stereoselective competitive inhibition of MAO A was found with the R enantiomer of salsolidine (Ki = 6 uM). Salsolidine also inhibits acetylcholinesterase (AChE), and buytlcholinesterase (BChE). Salsolidine may inhibit catechol-O-methyltransferase (COMT). Derivatives of salsolidine are neurotoxic and cytotoxic. R enantiomer of salsolidine is more potent than the S form.
CNS Activity
Originator
Sources: http://files.tk-team-iquir.webnode.com/200000099-45bd746ba6/Tetrahedron%20Asymmetry%202004%2015%201205.pdf
Curator's Comment: Salsolidine was first isolated by Proskurnina and Orekhov from Salsola richteri (Chenopodiaceae) as the levorotatory enantiomer (-)-1 [(S)-salsolidine]
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1951 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2296014 |
6.0 µM [Ki] | ||
Target ID: CHEMBL2023 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2490067 |
0.19 mM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
A dual anchoring strategy for the localization and activation of artificial metalloenzymes based on the biotin-streptavidin technology. | 2013 Apr 10 |
|
Synthesis of 1-substituted tetrahydroisoquinolines by lithiation and electrophilic quenching guided by in situ IR and NMR spectroscopy and application to the synthesis of salsolidine, carnegine and laudanosine. | 2013 Jun 10 |
|
Structural, kinetic, and docking studies of artificial imine reductases based on biotin-streptavidin technology: an induced lock-and-key hypothesis. | 2014 Nov 5 |
Patents
Sample Use Guides
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2296014
Stereoselective competitive inhibition of MAO A was found with the R enantiomer of salsolidine (Ki = 6 uM).
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493-48-1
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SUBSTANCE RECORD