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Details

Stereochemistry RACEMIC
Molecular Formula C19H23NO
Molecular Weight 281.392
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BLARCAMESINE

SMILES

CN(C)CC1CCOC1(C2=CC=CC=C2)C3=CC=CC=C3

InChI

InChIKey=BOTHKNZTGGXFEQ-UHFFFAOYSA-N
InChI=1S/C19H23NO/c1-20(2)15-18-13-14-21-19(18,16-9-5-3-6-10-16)17-11-7-4-8-12-17/h3-12,18H,13-15H2,1-2H3

HIDE SMILES / InChI
Molecular Formula C19H23NO
Molecular Weight 281.392
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19596910 | https://clinicaltrials.gov/ct2/show/NCT02756858 | https://www.ncbi.nlm.nih.gov/pubmed/19331132 | https://clinicaltrials.gov/ct2/show/NCT02244541 | https://www.ncbi.nlm.nih.gov/pubmed/11976553

AE-37 (ANAVEX2-73, Tetrahydro-N, N-dimethyl-2, 2-diphenyl-3-furanemethanamine) is an orally available drug candidate developed to potentially modify Alzheimer’s disease rather than temporarily address its symptoms. It has a clean Phase 1 data profile and shows a reversal of memory loss (anti-amnesic properties) and neuroprotection in several models of Alzheimer’s disease. This drug is in Phase II trials for Alzheimer's disease, phase I trials for epilepsy, and in preclinical trials for amyotrophic lateral sclerosis, Parkinson's disease, Rett syndrome, stroke. AE-37 may function as a pro-drug for ANAVEX19-144 and acts as a muscarinic receptor and a moderate sigma1 receptor agonist.

CNS Activity

Originator

Foscolos, G.B.|Kolocouris, N.|Fytas, G.|Marakos, P.|Pouli, N.|Vamvakides, A.
2
Sources: http://www.anavex.com/about-us/overview/Farmaco (1996), 51, (1), 19-26
Curator's Comment: https://www.google.com/patents/US20140228375

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2752
Sigma non-opioid intracellular receptor 1
26
Target ID: Q99720|||Q7Z653
Gene ID: 10280.0
Gene Symbol: SIGMAR1
Target Organism: Homo sapiens (Human)
Agonist
2752
Agonist
2752
 860.0 nM [IC50]
Modulator
846
 8.0 µM [IC50]
Modulator
846
 5.1 µM [IC50]
Modulator
846
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Phase I
438
Unknown

Approved Use

Unknown
Primary
Phase I
438
Unknown

Approved Use

Unknown
Primary
Phase I
438
Unknown

Approved Use

Unknown
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
5 mg 1 times / day multiple, intravenous
Highest studied dose
Dose: 5 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/32318621/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
https://pubmed.ncbi.nlm.nih.gov/32318621/
Sources:
https://pubmed.ncbi.nlm.nih.gov/32318621/
60 mg 1 times / day multiple, oral
Highest studied dose
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
https://www.anavex.com/anavex-announces-positive-phase-1-data-for-anavex-2-73-lead-candidate-for-the-treatment-of-alzheimers/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
https://www.anavex.com/anavex-announces-positive-phase-1-data-for-anavex-2-73-lead-candidate-for-the-treatment-of-alzheimers/
Other AEs: Dizziness, headache...
Other AEs:
Dizziness (moderate)
headache (moderate)
Sources:
https://www.anavex.com/anavex-announces-positive-phase-1-data-for-anavex-2-73-lead-candidate-for-the-treatment-of-alzheimers/
55 mg 1 times / day multiple, oral
MTD
Dose: 55 mg, 1 times / day
Route: oral
Route: multiple
Dose: 55 mg, 1 times / day
Sources:
https://www.anavex.com/anavex-announces-positive-phase-1-data-for-anavex-2-73-lead-candidate-for-the-treatment-of-alzheimers/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
https://www.anavex.com/anavex-announces-positive-phase-1-data-for-anavex-2-73-lead-candidate-for-the-treatment-of-alzheimers/
Sources:
https://www.anavex.com/anavex-announces-positive-phase-1-data-for-anavex-2-73-lead-candidate-for-the-treatment-of-alzheimers/
AEs

AEs

AESignificanceDosePopulation
Dizziness moderate
60 mg 1 times / day multiple, oral
Highest studied dose
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
https://www.anavex.com/anavex-announces-positive-phase-1-data-for-anavex-2-73-lead-candidate-for-the-treatment-of-alzheimers/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
https://www.anavex.com/anavex-announces-positive-phase-1-data-for-anavex-2-73-lead-candidate-for-the-treatment-of-alzheimers/
headache moderate
60 mg 1 times / day multiple, oral
Highest studied dose
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
https://www.anavex.com/anavex-announces-positive-phase-1-data-for-anavex-2-73-lead-candidate-for-the-treatment-of-alzheimers/
healthy, ADULT
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
https://www.anavex.com/anavex-announces-positive-phase-1-data-for-anavex-2-73-lead-candidate-for-the-treatment-of-alzheimers/
PubMed

PubMed

TitleDatePubMed
[Anticonvulsant and forced swim anti-immobility effects of tetrahydro-N, N-dimethyl-2,2-diphenyl-3-furanemethanamine (AE37): common action mechanism?].
2002 Mar
Anti-amnesic and neuroprotective potentials of the mixed muscarinic receptor/sigma 1 (σ1) ligand ANAVEX2-73, a novel aminotetrahydrofuran derivative.
2011 Aug
Blockade of Tau hyperphosphorylation and Aβ₁₋₄₂ generation by the aminotetrahydrofuran derivative ANAVEX2-73, a mixed muscarinic and σ₁ receptor agonist, in a nontransgenic mouse model of Alzheimer's disease.
2013 Aug
Mitochondrial protection by the mixed muscarinic/σ1 ligand ANAVEX2-73, a tetrahydrofuran derivative, in Aβ25-35 peptide-injected mice, a nontransgenic Alzheimer's disease model.
2014
Alzheimer's Association International Conference on Alzheimer's Disease 2015 (AAIC 2015) (July 18-23, 2015 - Washington, D.C., USA).
2015 Jul
Protection by sigma-1 receptor agonists is synergic with donepezil, but not with memantine, in a mouse model of amyloid-induced memory impairments.
2016 Jan 1
Patents

Patents

GR99100386
2
US20140228375
2
WO9730983
2

Sample Use Guides

In Vivo Use Guide
once daily oral (30mg/50mg) and IV (3mg/5mg) administration
Route of Administration: Other
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Wed Apr 02 06:52:41 GMT 2025
Edited
by admin
on Wed Apr 02 06:52:41 GMT 2025
Record UNII
9T210MMZ3F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BLARCAMESINE
INN   USAN  
Official Name English
ANAVEX 2-73
Preferred Name English
RAC-1-((3R)-2,2-DIPHENYLOXOLAN-3-YL)-N,N-DIMETHYLMETHANAMINE
Systematic Name English
blarcamesine [INN]
Common Name English
BLARCAMESINE [USAN]
Common Name English
Blarcamesine [WHO-DD]
Common Name English
3-FURANMETHANAMINE, TETRAHYDRO-N,N-DIMETHYL-2,2-DIPHENYL-
Systematic Name English
TETRAHYDRO-N,N-DIMETHYL-2,2-DIPHENYL-3-FURANMETHANAMINE
Systematic Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 908022
Created by admin on Wed Apr 02 06:52:41 GMT 2025 , Edited by admin on Wed Apr 02 06:52:41 GMT 2025
Code System Code Type Description
INN
11031
Created by admin on Wed Apr 02 06:52:41 GMT 2025 , Edited by admin on Wed Apr 02 06:52:41 GMT 2025
PRIMARY
USAN
FG-91
Created by admin on Wed Apr 02 06:52:41 GMT 2025 , Edited by admin on Wed Apr 02 06:52:41 GMT 2025
PRIMARY
PUBCHEM
9882189
Created by admin on Wed Apr 02 06:52:41 GMT 2025 , Edited by admin on Wed Apr 02 06:52:41 GMT 2025
PRIMARY
NCI_THESAURUS
C171846
Created by admin on Wed Apr 02 06:52:41 GMT 2025 , Edited by admin on Wed Apr 02 06:52:41 GMT 2025
PRIMARY
EVMPD
SUB197746
Created by admin on Wed Apr 02 06:52:41 GMT 2025 , Edited by admin on Wed Apr 02 06:52:41 GMT 2025
PRIMARY
SMS_ID
100000183265
Created by admin on Wed Apr 02 06:52:41 GMT 2025 , Edited by admin on Wed Apr 02 06:52:41 GMT 2025
PRIMARY
CAS
195615-83-9
Created by admin on Wed Apr 02 06:52:41 GMT 2025 , Edited by admin on Wed Apr 02 06:52:41 GMT 2025
PRIMARY
EPA CompTox
DTXSID60941344
Created by admin on Wed Apr 02 06:52:41 GMT 2025 , Edited by admin on Wed Apr 02 06:52:41 GMT 2025
PRIMARY
FDA UNII
9T210MMZ3F
Created by admin on Wed Apr 02 06:52:41 GMT 2025 , Edited by admin on Wed Apr 02 06:52:41 GMT 2025
PRIMARY
WIKIPEDIA
Blarcamesine
Created by admin on Wed Apr 02 06:52:41 GMT 2025 , Edited by admin on Wed Apr 02 06:52:41 GMT 2025
PRIMARY
DRUG BANK
DB05592
Created by admin on Wed Apr 02 06:52:41 GMT 2025 , Edited by admin on Wed Apr 02 06:52:41 GMT 2025
PRIMARY
Related Record Type Details
SIGMA NON-OPIOID INTRACELLULAR RECEPTOR 1
TARGET -> AGONIST
MUSCARINIC ACETYLCHOLINE RECEPTOR M1
TARGET->MODULATOR
Structure of BLARCAMESINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of BLARCAMESINE
ACTIVE MOIETY
NIH
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