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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
Structure of SALSOLIDINE

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

HIDE SMILES / InChI
Molecular Formula C12H17NO2
Molecular Weight 207.2689
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Proskurnina, N.|Orekhov, A.
1
Curator's Comment: Salsolidine was first isolated by Proskurnina and Orekhov from Salsola richteri (Chenopodiaceae) as the levorotatory enantiomer (-)-1 [(S)-salsolidine]

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 6.0 µM [Ki]
Inhibitor
8297
 0.19 mM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
Patents

Patents

04766131
4

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Stereoselective competitive inhibition of MAO A was found with the R enantiomer of salsolidine (Ki = 6 uM).
Substance Class Chemical
Created
by admin
on Fri Dec 15 20:16:51 GMT 2023
Edited
by admin
on Fri Dec 15 20:16:51 GMT 2023
Record UNII
QMS4D62O1I
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SALSOLIDINE
Common Name English
(S)-(-)-SALSOLIDINE
Common Name English
(S)-6,7-DIMETHOXY-1-METHYL-1,2,3,4-TETRAHYDROISOQUINOLINE
Systematic Name English
SALSOLIDIN
Common Name English
ISOQUINOLINE, 1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-1-METHYL-, (S)-
Systematic Name English
(-)-SALSOLIDINE
Common Name English
SALSOLIDINE, (-)-
Common Name English
ISOQUINOLINE, 1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-1-METHYL-, (1S)-
Systematic Name English
(S)-SALSOLIDINE
Common Name English
Code System Code Type Description
PUBCHEM
164752
Created by admin on Fri Dec 15 20:16:51 GMT 2023 , Edited by admin on Fri Dec 15 20:16:51 GMT 2023
PRIMARY
FDA UNII
QMS4D62O1I
Created by admin on Fri Dec 15 20:16:51 GMT 2023 , Edited by admin on Fri Dec 15 20:16:51 GMT 2023
PRIMARY
CAS
493-48-1
Created by admin on Fri Dec 15 20:16:51 GMT 2023 , Edited by admin on Fri Dec 15 20:16:51 GMT 2023
PRIMARY
NIH
NCATS
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