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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2017-11-21 17:42:22 UTC
Update Date2019-07-23 14:38:55 UTC
HMDB IDHMDB0240240
Secondary Accession NumbersNone
Metabolite Identification
Common NameLatrepirdine
DescriptionLatrepirdine belongs to the class of organic compounds known as n-alkylindoles. N-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 1-position. Latrepirdine is a very strong basic compound (based on its pKa). In humans, latrepirdine is involved in latrepirdine h1-antihistamine action. Research suggests it may also have cognition-enhancing effects in healthy individuals, in the absence of neurodegenerative disease pathology. Research was conducted in both Russia and western nations into potential applications as a neuroprotective drug to treat Alzheimer's disease and, possibly, as a nootropic, as well. The trial was sponsored by Medivation Inc. and Pfizer. Latrepirdine showed promising results in a phase III-equivalent, double-blind trial in Russia with mild–moderate stage patients. A Cochrane meta-analysis of the three pivotal phase III efficacy trials found no significant effect of latrepirdine on cognition and function in mild-to-moderate Alzheimer's patients, though there appears to be a modest benefit for overall behavior disturbances. With CONCERT, the remaining Pfizer and Medivation Phase III trial for latrepirdine in Alzheimer's disease failed in 2012, effectively ending the development in this indication.
Structure
Data?1563892735
Synonyms
ValueSource
DimebolinHMDB
DimebolineHMDB
DimebonHMDB, MeSH
DimeboneHMDB, MeSH
Preparation 84HMDB
LatrepirdineHMDB
Chemical FormulaC21H25N3
Average Molecular Weight319.452
Monoisotopic Molecular Weight319.204847817
IUPAC Name5-(2-{2,8-dimethyl-1H,2H,3H,4H,5H-pyrido[4,3-b]indol-5-yl}ethyl)-2-methylpyridine
Traditional Namelatrepirdine
CAS Registry Number3613-73-8
SMILES
CN1CCC2=C(C1)C1=CC(C)=CC=C1N2CCC1=CC=C(C)N=C1
InChI Identifier
InChI=1S/C21H25N3/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
InChI KeyJNODQFNWMXFMEV-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as n-alkylindoles. N-alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 1-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassN-alkylindoles
Direct ParentN-alkylindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • N-alkylindole
  • Indole
  • Methylpyridine
  • Aralkylamine
  • Pyridine
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Amine
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.52ALOGPS
logP3.41ChemAxon
logS-4.3ALOGPS
pKa (Strongest Basic)7.17ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area21.06 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity100.72 m³·mol⁻¹ChemAxon
Polarizability38.6 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00di-0119000000-912c132b0c377d70b0b3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00fr-1492000000-e074b38ea87239a8c292Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-3900000000-abbbe3dcbd3e543a23a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0009000000-71b046122676d3980bbcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014j-4619000000-407ed46cd6f2005b6540Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0032-0900000000-89c2c2376cf7c2758389Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB11725
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLatrepirdine
METLIN IDNot Available
PubChem Compound197033
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Montgomery LC, Deuster PA: Effects of antihistamine medications on exercise performance. Implications for sportspeople. Sports Med. 1993 Mar;15(3):179-95. [PubMed:7680815 ]