SALSOLINE HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C11H15NO2.ClH
Molecular Weight	229.703
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=PZZVNEZKNWRZEG-OGFXRTJISA-N

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

HIDE SMILES / InChI

Molecular Formula	C11H15NO2
Molecular Weight	193.2423
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6935920 | https://www.ncbi.nlm.nih.gov/pubmed/2296014 | https://www.ncbi.nlm.nih.gov/pubmed/10456568 | https://www.ncbi.nlm.nih.gov/pubmed/17447417 | https://www.ncbi.nlm.nih.gov/pubmed/16336631 | https://www.ncbi.nlm.nih.gov/pubmed/15026514

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 Target	Pharmacology	Condition	Potency
Amine oxidase [flavin-containing] A 14 Target ID: P21397 Gene ID: 4128.0 Gene Symbol: MAOA Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/2296014	Inhibitor 8297		77.0 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Apoptotic cell death 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17447417 https://www.ncbi.nlm.nih.gov/pubmed/2296014 https://www.ncbi.nlm.nih.gov/pubmed/16336631	Diagnostic		Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Mitochondria determine the survival and death in apoptosis by an endogenous neurotoxin, N-methyl(R)salsolinol, and neuroprotection by propargylamines.	2002 May	12111453
Tetrahydroisoquinoline derivatives of enkephalins: synthesis and properties.	2002 May 15	12034373
Cell death in Parkinson's disease.	2002 Sep	12375057
Dopamine-derived endogenous N-methyl-(R)-salsolinol: its role in Parkinson's disease.	2002 Sep-Oct	12200189
Simultaneous gas chromatographic-mass spectrometric determination of dopamine, norsalsolinol and salsolinol enantiomers in brain samples of a large human collective.	2003 Jul	14528920
Tetrahydroisoquinoline and beta-carboline alkaloids from Haloxylon articulatum (Cav.) Bunge (Chenopodiaceae).	2003 Jul-Aug	12939030
N-methyl-norsalsolinol modulates serotonin metabolism in the rat caudate nucleus: correlation with behavioural changes.	2003 Mar	12899734
Increased systemic levels of norsalsolinol derivatives are induced by levodopa treatment and do not represent biological markers of Parkinson's disease.	2004 Apr	15026514
Quantification of salsolinol enantiomers by stable isotope dilution liquid chromatography with tandem mass spectrometric detection.	2008 Dec	19034892
A new microdialysis-electrochemical device for in vivo simultaneous determination of acetylcholine and choline in rat brain treated with N-methyl-(R)-salsolinol.	2009 Aug 15	19523811

Patents

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 Created by `admin` on `Fri Dec 15 22:12:09 GMT 2023` Edited by `admin` on `Fri Dec 15 22:12:09 GMT 2023`
Record UNII	JYW06894PT
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SALSOLINE HYDROCHLORIDE

Common Name

English

SALSOLINE HYDROCHLORIDE [MI]

Common Name

English

(R)-(+)-SALSOLINE HYDROCHLORIDE

Common Name

English

6-ISOQUINOLINOL, 1,2,3,4-TETRAHYDRO-7-METHOXY-1-METHYL-, HYDROCHLORIDE (1:1), (1R)-

Common Name

English

(+)-SALSOLINE HYDROCHLORIDE

Common Name

English

6-ISOQUINOLINOL, 1,2,3,4-TETRAHYDRO-7-METHOXY-1-METHYL-, HYDROCHLORIDE, (1R)-

Systematic Name

English

SALSOLINE HYDROCHLORIDE, (+)-

Common Name

English

6-ISOQUINOLINOL, 1,2,3,4-TETRAHYDRO-7-METHOXY-1-METHYL-, HYDROCHLORIDE, (R)-

Systematic Name

English

Code System Code Type Description

FDA UNII

JYW06894PT