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Details

Stereochemistry ABSOLUTE
Molecular Formula C11H15NO2
Molecular Weight 193.2423
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SALSOLINE

SMILES

COC1=CC2=C(CCN[C@@H]2C)C=C1O

InChI

InChIKey=YTPRLBGPGZHUPD-SSDOTTSWSA-N
InChI=1S/C11H15NO2/c1-7-9-6-11(14-2)10(13)5-8(9)3-4-12-7/h5-7,12-13H,3-4H2,1-2H3/t7-/m1/s1

HIDE SMILES / InChI

Molecular Formula C11H15NO2
Molecular Weight 193.2423
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Salsoline is a metabolite of dopamine and is highly prevalent in the urine and cerebrospinal fluid of alcoholics at the time of intoxication and for several days after. Salsoline and related compounds bind to the Type A Mono-amine Oxidase inducing neuronal cell death. At one time salsoline was thought to be a biomarker for Parkinson's disease. However, it was later shown that treatment regimes result in an increased endogenous concentration of salsoline and related compounds.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
77.0 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
highly purified Monoamine oxidase A and B were tested with a series of isoquinolines. Stereoselective competitive inhibition of MAO-A was observed for the R enantiomer of salsoline (Ki = 77 micro-M). Salsoline did not show meaningful inhibition of MAO-B.
Substance Class Chemical
Record UNII
9Q83ETU10C
Record Status Validated (UNII)
Record Version