3-Amino-1,4-dimethyl-5H-pyrido [4,3-b]indole (CHEM003584)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2014-09-08 02:38:09 UTC
Update Date2016-11-09 01:09:10 UTC
Accession NumberCHEM003584
Identification
Common Name3-Amino-1,4-dimethyl-5H-pyrido [4,3-b]indole
ClassSmall Molecule
Description3-amino-1,4-dimethyl-5H-pyrido[4,3-b]indole (Trp-P-1) is one of the potent food-born dietary carcinogens derived mainly from burnt meat products. The activation of heterocyclic amines, including Trp-P-1, to reactive metabolites is a critical step to exhibit its carcinogenic effects ( Chun et al., 2000, Shiotani et al., 2001 and Kato, 1986). At the initial phase in the carcinogenic process, an exocyclic amino group of Trp-P-1 is metabolically activated to hydroxyamino derivatives by cytochrome P450 to form DNA adducts, which are considered as a main cause of DNA damage during the carcinogenic process in vitro and in vivo ( Shiotani and Ashida, 2004, Inami and Mochizuki, 2002 and Hatanaka et al., 2001). On the other hand, Trp-P-1 can also directly interact with DNA and induces chromosomal aberrations ( Shiotani and Ashida, 2004), suggesting that Trp-P-1 can cause DNA damage without metabolic activation to the N-hydroxyl form. DNA damage triggers not only mutation and carcinogenesis but also apoptosis ( Hashimoto et al., 2004 and Shiotani and Ashida, 2004), indeed 2-acetamidofluorane, a chemical carcinogen with a Trp-P-1-related structure, shows a cytotoxic effect on hepatocytes ( Ashida et al., 1998) and induced apoptosis in the rat liver in vivo.
Contaminant Sources
  • FooDB Chemicals
  • IARC Carcinogens Group 2B
  • T3DB toxins
  • Tobacco Smoke Compounds
Contaminant Type
  • Cigarette Toxin
  • Food Toxin
  • Metabolite
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1,4-Dimethyl-5H-pyrido(4,3-b)indol-3-amineHMDB
1,4-Dimethyl-5H-pyrido[4,3-b]indol-3-amine, 9ciHMDB
1,4-Dimethyl-9H-pyrido(4,3-b)indol-3-amineHMDB
3-Amino-1,4-dimethyl-5H-pyrido(4,3-b)indoleHMDB
3-Amino-1,4-dimethyl-g-carbolineHMDB
3-Amino-1,4-dimethyl-gamma-carbolineHMDB
TRP-1HMDB
TRP-p-1HMDB
TRP-P1HMDB
Tryptophan P1HMDB
Tryptophan-p-1HMDB
Trytophan pyrolysate 1HMDB
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indoleKEGG
Chemical FormulaC13H13N3
Average Molecular Mass211.262 g/mol
Monoisotopic Mass211.111 g/mol
CAS Registry Number62450-06-0
IUPAC Name1,4-dimethyl-5H-pyrido[4,3-b]indol-3-amine
Traditional Name1,4-dimethyl-5H-pyrido[4,3-b]indol-3-amine
SMILESCC1=C2C(NC3=CC=CC=C23)=C(C)C(N)=N1
InChI IdentifierInChI=1S/C13H13N3/c1-7-12-11(8(2)15-13(7)14)9-5-3-4-6-10(9)16-12/h3-6,16H,1-2H3,(H2,14,15)
InChI KeyLVTKHGUGBGNBPL-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as gamma carbolines. These are polycyclic aromatic compounds containing a gamma-carbazole(5H-pyrido[4,3-b]indole) moiety, with a structure characterized by the presence of pyridine fused to the pyrrole ring of an indole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassPyridoindoles
Direct ParentGamma carbolines
Alternative Parents
Substituents
  • Gamma-carboline
  • Indole
  • Pyrrolopyridine
  • Aminopyridine
  • Methylpyridine
  • Imidolactam
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Hydrocarbon derivative
  • Primary amine
  • Organonitrogen compound
  • Amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Cytosol
  • Extracellular
  • Microsome
  • Mitochondrion
Biofluid LocationsNot Available
Tissue LocationsNot Available
Pathways
NameSMPDB LinkKEGG Link
ApoptosisNot Availablemap04210
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point252 - 262 °C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.055 g/LALOGPS
logP2.73ALOGPS
logP2.28ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)13.45ChemAxon
pKa (Strongest Basic)9.97ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area54.7 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity65.96 m³·mol⁻¹ChemAxon
Polarizability23.86 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01ox-6920000000-bc93105c1d081ec984b7Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-01ox-6920000000-bc93105c1d081ec984b7Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dj-0930000000-36b5d2d7bf0b59d1b39bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-99d523d2d9b243b038afSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0690000000-2b58ed661612ed6a86a7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kb-0900000000-47965f0b341d97a19de6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-1090000000-f592d074259bb2ab388fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-1190000000-dd2a6c3bfecff2ce6023Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9600000000-81184911da8b853890ffSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0090000000-4dafdcd63f1115768fe9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0090000000-bda0e0b196243b2f2b49Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0296-0910000000-9ff4ea4f5ec8709952f7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0090000000-151eb25ddf9df2d6bfbeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0090000000-151eb25ddf9df2d6bfbeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-0910000000-59be513918c2decfcf14Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (10)
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0029746
FooDB IDFDB000947
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4447538
ChEBI IDNot Available
PubChem Compound ID5284474
Kegg Compound IDC19306
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Bae YK, Qin H, Knobel KM, Hu J, Rosenbaum JL, Barr MM: General and cell-type specific mechanisms target TRPP2/PKD-2 to cilia. Development. 2006 Oct;133(19):3859-70. Epub 2006 Aug 30.
2. Awney HA, Sindi H: The effect of rosemary on the mutagenic activity of heterocyclic amines extracted from common food consumed in Saudi Arabia. Int J Food Sci Nutr. 2010 Mar;61(2):192-203. doi: 10.3109/09637480903294953.
3. Woudenberg-Vrenken TE, Bindels RJ, Hoenderop JG: The role of transient receptor potential channels in kidney disease. Nat Rev Nephrol. 2009 Aug;5(8):441-9. doi: 10.1038/nrneph.2009.100. Epub 2009 Jun 23.
4. Mene P: Transient receptor potential channels in the kidney: calcium signaling, transport and beyond. J Nephrol. 2006 Jan-Feb;19(1):21-9.
5. Yin J, Kuebler WM: Mechanotransduction by TRP channels: general concepts and specific role in the vasculature. Cell Biochem Biophys. 2010;56(1):1-18. doi: 10.1007/s12013-009-9067-2.
6. Sharif-Naeini R, Folgering JH, Bichet D, Duprat F, Lauritzen I, Arhatte M, Jodar M, Dedman A, Chatelain FC, Schulte U, Retailleau K, Loufrani L, Patel A, Sachs F, Delmas P, Peters DJ, Honore E: Polycystin-1 and -2 dosage regulates pressure sensing. Cell. 2009 Oct 30;139(3):587-96. doi: 10.1016/j.cell.2009.08.045.
7. Kwan HY, Huang Y, Yao X: TRP channels in endothelial function and dysfunction. Biochim Biophys Acta. 2007 Aug;1772(8):907-14. Epub 2007 Mar 12.
8. Laycock S, Taylor HC, Haigh C, Lee AT, Cooper GJ, Ong AC, Robson L: A novel dephosphorylation-activated conductance in a mouse renal collecting duct cell line. Exp Physiol. 2009 Aug;94(8):914-27. doi: 10.1113/expphysiol.2009.047753. Epub 2009 May 8.
9. Beech DJ, Muraki K, Flemming R: Non-selective cationic channels of smooth muscle and the mammalian homologues of Drosophila TRP. J Physiol. 2004 Sep 15;559(Pt 3):685-706. Epub 2004 Jul 22.
10. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.