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Details

Stereochemistry ACHIRAL
Molecular Formula C21H25N3.2ClH
Molecular Weight 392.365
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LATREPIRDINE DIHYDROCHLORIDE

SMILES

Cl.Cl.CN1CCC2=C(C1)C3=C(C=CC(C)=C3)N2CCC4=CC=C(C)N=C4

InChI

InChIKey=GTWLIQOLGOZTLF-UHFFFAOYSA-N
InChI=1S/C21H25N3.2ClH/c1-15-4-7-20-18(12-15)19-14-23(3)10-9-21(19)24(20)11-8-17-6-5-16(2)22-13-17;;/h4-7,12-13H,8-11,14H2,1-3H3;2*1H

HIDE SMILES / InChI
Molecular Formula C21H25N3
Molecular Weight 319.4433
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/21031168 | https://www.ncbi.nlm.nih.gov/pubmed/18939977

Dimebon (latrepirdine) is an orally available, small molecule, gamma carboline derivative that was developed and used in Russia as an over-the-counter oral antihistamine for allergy treatment since 1980s. In 1990s it was shown that Dimebon has promising potential in treating neurodegenerative diseases. In 2003, Medivation Inc acquired the rights to Dimebon. Medivation went public in December 2004, with Dimebon as the only drug in its pipeline. The product was being developed by Medivation and Pfizer as a treatment for early-stage Alzheimer's disease and Huntington's disease. However, development was discontinued by Medivation and Pfizer in early 2012. Dimebon inhibits alpha-Adrenergic receptors (alpha1A, alpha1B, alpha1D, and alpha2A), Histamine H1 and H2 receptors and Serotonin 5-HT2c, 5-HT5A, 5-HT6 receptors with high affinity. Dimebon may act by blocking NMDA receptors or voltage-gated Ca2+ channels and by preventing mitochondrial permeability pore transition.

CNS Activity

Originator

Shadurski, K.S. et al.
2
Sources: Shadurski KS, Danusevich IK, Kost AN, Vinogradova EV. 1138164 US Patent No. Chem Abstr. 1985;102:190810.
Curator's Comment: Reference retrieved from https://www.ncbi.nlm.nih.gov/pubmed/21517088

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
Antagonist
2849
Inhibitor
8504
 42.0 µM [IC50]
Inhibitor
8504
 7.9 µM [IC50]
Blocker
555
 57.0 µM [IC50]
Inhibitor
8504
Inhibitor
8504
Inhibitor
8504
Inhibitor
8504
Inhibitor
8504
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
Dimebon

Approved Use

Dimebon was initially developed and launched in Russia (USSR at the time) in 1983 as an over-the-counter oral antihistamine for allergy treatment.

Launch Date

1982
Primary
Phase III
665
Unknown

Approved Use

Unknown
Primary
Phase III
665
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.0122 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/33898159/
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LATREPIRDINE unknown
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.03 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/33898159/
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LATREPIRDINE unknown
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
1.3 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27072954/
8.14 mg single, oral
dose: 8.14 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LATREPIRDINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
0.0645 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/33898159/
20 mg single, oral
dose: 20 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LATREPIRDINE unknown
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
0.149 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/33898159/
40 mg single, oral
dose: 40 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LATREPIRDINE unknown
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
10.4 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27072954/
8.14 mg single, oral
dose: 8.14 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LATREPIRDINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
6.8 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/27072954/
8.14 mg single, oral
dose: 8.14 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
LATREPIRDINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
20 mg 3 times / day multiple, oral
Studied dose
Dose: 20 mg, 3 times / day
Route: oral
Route: multiple
Dose: 20 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/20142523/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/20142523/
Disc. AE: Loss of consciousness, Rash...
AEs leading to
discontinuation/dose reduction:
Loss of consciousness (grade 3, 2.2%)
Rash (2.2%)
Headache (2.2%)
Renal and urinary disorders (2.2%)
Supraventricular tachycardia (2.2%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/20142523/
AEs

AEs

AESignificanceDosePopulation
Headache 2.2%
Disc. AE
20 mg 3 times / day multiple, oral
Studied dose
Dose: 20 mg, 3 times / day
Route: oral
Route: multiple
Dose: 20 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/20142523/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/20142523/
Rash 2.2%
Disc. AE
20 mg 3 times / day multiple, oral
Studied dose
Dose: 20 mg, 3 times / day
Route: oral
Route: multiple
Dose: 20 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/20142523/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/20142523/
Renal and urinary disorders 2.2%
Disc. AE
20 mg 3 times / day multiple, oral
Studied dose
Dose: 20 mg, 3 times / day
Route: oral
Route: multiple
Dose: 20 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/20142523/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/20142523/
Supraventricular tachycardia 2.2%
Disc. AE
20 mg 3 times / day multiple, oral
Studied dose
Dose: 20 mg, 3 times / day
Route: oral
Route: multiple
Dose: 20 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/20142523/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/20142523/
Loss of consciousness grade 3, 2.2%
Disc. AE
20 mg 3 times / day multiple, oral
Studied dose
Dose: 20 mg, 3 times / day
Route: oral
Route: multiple
Dose: 20 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/20142523/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/20142523/
PubMed

PubMed

TitleDatePubMed
Latrepirdine improves cognition and arrests progression of neuropathology in an Alzheimer's mouse model.
2013-08
The rise and fall of Dimebon.
2010-10
Evaluation of Dimebon in cellular model of Huntington's disease.
2008-10-21
Effect of dimebon on cognition, activities of daily living, behaviour, and global function in patients with mild-to-moderate Alzheimer's disease: a randomised, double-blind, placebo-controlled study.
2008-07-19
Antihistamine agent Dimebon as a novel neuroprotector and a cognition enhancer.
2001-06
Patents

Patents

08338408
2
WO2008036400A3
2
WO2008051599A3
2
WO2008112238A1
2

Sample Use Guides

In Vivo Use Guide
As anti-allergic medicine Dimebon was used in doses 10–20 mg 2–3 times per day. Oral dimebon, 20 mg three times a day was tested in Alzheimer's disease patients.
Route of Administration: Oral
In Vitro Use Guide
50 uM Dimebon stabilized glutamate-induced Ca2+ signals in primary striatal neuronal cultures (MSN) from YAC128 HD transgenic mice (YAC128 MSN) and protected cultured YAC128 MSN from glutamate-induced apoptosis. Lower concentrations of Dimebon (5 uM and 10 uM) did not stabilize glutamate-induced Ca2+ signals and did not exert neuroprotective effects in experiments with YAC128 MSN.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:18:29 GMT 2025
Edited
by admin
on Mon Mar 31 18:18:29 GMT 2025
Record UNII
8B9414QQ5M
Record Status Validated (UNII)
Record Version
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Name Type Language
LATREPIRDINE DIHYDROCHLORIDE
USAN   WHO-DD  
USAN  
Official Name English
DIMEBOLIN DIHYDROCHLORIDE
MI  
Preferred Name English
DIMEBON DIHYDROCHLORIDE
Common Name English
Latrepirdine dihydrochloride [WHO-DD]
Common Name English
2,8-Dimethyl-5-[2-(6-methylpyridin-3-yl)ethyl]-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole dihydrochloride
Systematic Name English
DIMEBOLIN HYDROCHLORIDE
Common Name English
1H-PYRIDO(4,3-B)INDOLE, 2,3,4,5-TETRAHYDRO-2,8-DIMETHYL-5-(2-(6-METHYL-3-PYRIDINYL)ETHYL)-, DIHYDROCHLORIDE
Common Name English
LATREPIRDINE DIHYDROCHLORIDE [USAN]
Common Name English
9-(2-(2-METHYLPYRIDYL-5)ETHYL)-3,6-DIMETHYL-1,2,3,4-TETRAHYDRO-.GAMMA.-CARBOLINE 2HCL
Common Name English
1H-PYRIDO(4,3-B)INDOLE, 2,3,4,5-TETRAHYDRO-2,8-DIMETHYL-5-(2-(6-METHYL-3- PYRIDINYL)ETHYL)-, HYDROCHLORIDE (1:2)
Systematic Name English
DIMEBOLIN DIHYDROCHLORIDE [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29578
Created by admin on Mon Mar 31 18:18:29 GMT 2025 , Edited by admin on Mon Mar 31 18:18:29 GMT 2025
Code System Code Type Description
EU-Orphan Drug
EU/3/08/597(WITHDRAWN)
Created by admin on Mon Mar 31 18:18:29 GMT 2025 , Edited by admin on Mon Mar 31 18:18:29 GMT 2025
PRIMARY Please note that this product was withdrawn from the Community Register of designated Orphan Medicinal Products in February 2015 on request of the Sponsor. On 20 January 2009, orphan designation (EU/3/08/597) was granted by the European Commission to Innovative Drug European Associates Limited, United Kingdom, for 2,3,4,5 tetrahydro-2,8-dimethyl-5-[2-(6-methyl-3-pyridinyl)ethyl]-1H-pyrido[4,3-b]indole dihydrochloride for the treatment of Huntington’s disease. In December 2012, Innovative Drug European Associates Limited changed name to IDEA Innovative Drug European Associates Limited.
PUBCHEM
23729232
Created by admin on Mon Mar 31 18:18:29 GMT 2025 , Edited by admin on Mon Mar 31 18:18:29 GMT 2025
PRIMARY
SMS_ID
100000183860
Created by admin on Mon Mar 31 18:18:29 GMT 2025 , Edited by admin on Mon Mar 31 18:18:29 GMT 2025
PRIMARY
EVMPD
SUB32956
Created by admin on Mon Mar 31 18:18:29 GMT 2025 , Edited by admin on Mon Mar 31 18:18:29 GMT 2025
PRIMARY
FDA UNII
8B9414QQ5M
Created by admin on Mon Mar 31 18:18:29 GMT 2025 , Edited by admin on Mon Mar 31 18:18:29 GMT 2025
PRIMARY
EPA CompTox
DTXSID10243103
Created by admin on Mon Mar 31 18:18:29 GMT 2025 , Edited by admin on Mon Mar 31 18:18:29 GMT 2025
PRIMARY
USAN
WW-165
Created by admin on Mon Mar 31 18:18:29 GMT 2025 , Edited by admin on Mon Mar 31 18:18:29 GMT 2025
PRIMARY
NCI_THESAURUS
C78758
Created by admin on Mon Mar 31 18:18:29 GMT 2025 , Edited by admin on Mon Mar 31 18:18:29 GMT 2025
PRIMARY
CAS
97657-92-6
Created by admin on Mon Mar 31 18:18:29 GMT 2025 , Edited by admin on Mon Mar 31 18:18:29 GMT 2025
PRIMARY
MERCK INDEX
m4495
Created by admin on Mon Mar 31 18:18:29 GMT 2025 , Edited by admin on Mon Mar 31 18:18:29 GMT 2025
PRIMARY Merck Index
ChEMBL
CHEMBL589390
Created by admin on Mon Mar 31 18:18:29 GMT 2025 , Edited by admin on Mon Mar 31 18:18:29 GMT 2025
PRIMARY
Related Record Type Details
Structure of LATREPIRDINE
ACTIVE MOIETY
NIH
NCATS
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