U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C13H14N2O
Molecular Weight 214.2631
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VELNACRINE

SMILES

NC1=C2C=CC=CC2=NC3=C1C(O)CCC3

InChI

InChIKey=HLVVITIHAZBPKB-UHFFFAOYSA-N
InChI=1S/C13H14N2O/c14-13-8-4-1-2-5-9(8)15-10-6-3-7-11(16)12(10)13/h1-2,4-5,11,16H,3,6-7H2,(H2,14,15)

HIDE SMILES / InChI
Molecular Formula C13H14N2O
Molecular Weight 214.2631
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Velnacrine (9-amino-1,2,3,4-tetrahydroacridin-1-ol) is an inhibitor of acetylcholinesterase. It was studied for the treatment of Alzheimer's disease however development was discontinued. There has been no research into the use of velnacrine as a cognitive enhancer in the treatment of Alzheimer's disease since 1994. The FDA peripheral and CNS drug advisory board voted unanimously against recommending approval. This review shows the toxic nature of velnacrine, and provides no evidence of efficacy.

CNS Activity

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 0.79 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1132
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Patents

Patents

US4631286
8

Sample Use Guides

In Vivo Use Guide
Velnacrine for the treatment of Alzheimer's disease (a double-blind, placebo-controlled trials): 10, 25, 50 and 75 mg t.i.d. The 225 mg/day dose appears to be safe for use in multicenter outpatient trials of velnacrine efficacy in Alzheimer's disease.
Route of Administration: Oral
In Vitro Use Guide
Human erythrocyte suspensions were incubated with acetylcholine and choline in the absence or presence of 10 microM atropine or 10 microM velnacrine maleate.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:27:14 UTC 2023
Edited
by admin
on Fri Dec 15 17:27:14 UTC 2023
Record UNII
Y2P6NV151K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VELNACRINE
INN   MI   WHO-DD  
INN  
Official Name English
1-ACRIDINOL, 9-AMINO-1,2,3,4-TETRAHYDRO-, (±)-
Systematic Name English
1-HYDROXYTACRINE
Common Name English
HYDROXYTACRINE
Common Name English
9-AMINO-1,2,3,4-TETRAHYDROACRIDIN-1-OL
Systematic Name English
1-ACRIDINOL, 9-AMINO-1,2,3,4-TETRAHYDRO-
Systematic Name English
VELNACRINE [MI]
Common Name English
(±)-9-AMINO-1,2,3,4-TETRAHYDRO-1-ACRIDINOL
Systematic Name English
velnacrine [INN]
Common Name English
1-OH-THA
Common Name English
Velnacrine [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C47792
Created by admin on Fri Dec 15 17:27:14 UTC 2023 , Edited by admin on Fri Dec 15 17:27:14 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL51934
Created by admin on Fri Dec 15 17:27:14 UTC 2023 , Edited by admin on Fri Dec 15 17:27:14 UTC 2023
PRIMARY
MERCK INDEX
m983
Created by admin on Fri Dec 15 17:27:14 UTC 2023 , Edited by admin on Fri Dec 15 17:27:14 UTC 2023
PRIMARY Merck Index
CAS
104675-29-8
Created by admin on Fri Dec 15 17:27:14 UTC 2023 , Edited by admin on Fri Dec 15 17:27:14 UTC 2023
SUPERSEDED
PUBCHEM
3655
Created by admin on Fri Dec 15 17:27:14 UTC 2023 , Edited by admin on Fri Dec 15 17:27:14 UTC 2023
PRIMARY
MESH
C056424
Created by admin on Fri Dec 15 17:27:14 UTC 2023 , Edited by admin on Fri Dec 15 17:27:14 UTC 2023
PRIMARY
FDA UNII
Y2P6NV151K
Created by admin on Fri Dec 15 17:27:14 UTC 2023 , Edited by admin on Fri Dec 15 17:27:14 UTC 2023
PRIMARY
SMS_ID
100000079097
Created by admin on Fri Dec 15 17:27:14 UTC 2023 , Edited by admin on Fri Dec 15 17:27:14 UTC 2023
PRIMARY
INN
6403
Created by admin on Fri Dec 15 17:27:14 UTC 2023 , Edited by admin on Fri Dec 15 17:27:14 UTC 2023
PRIMARY
EVMPD
SUB00033MIG
Created by admin on Fri Dec 15 17:27:14 UTC 2023 , Edited by admin on Fri Dec 15 17:27:14 UTC 2023
PRIMARY
EPA CompTox
DTXSID4046945
Created by admin on Fri Dec 15 17:27:14 UTC 2023 , Edited by admin on Fri Dec 15 17:27:14 UTC 2023
PRIMARY
DRUG CENTRAL
3848
Created by admin on Fri Dec 15 17:27:14 UTC 2023 , Edited by admin on Fri Dec 15 17:27:14 UTC 2023
PRIMARY
CAS
124027-47-0
Created by admin on Fri Dec 15 17:27:14 UTC 2023 , Edited by admin on Fri Dec 15 17:27:14 UTC 2023
PRIMARY
NCI_THESAURUS
C96773
Created by admin on Fri Dec 15 17:27:14 UTC 2023 , Edited by admin on Fri Dec 15 17:27:14 UTC 2023
PRIMARY
Related Record Type Details
Structure of VELNACRINE FUMARATE
SALT/SOLVATE -> PARENT
Structure of VELNACRINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of VELNACRINE MALEATE
SALT/SOLVATE -> PARENT
Structure of VELNACRINE, (+)-
ENANTIOMER -> RACEMATE
Structure of VELNACRINE, (-)-
ENANTIOMER -> RACEMATE
Related Record Type Details
Structure of TACRINE
PARENT -> METABOLITE ACTIVE
URINE
Related Record Type Details
Structure of VELNACRINE
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966