Hmdb loader
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:32:22 UTC
Update Date2022-03-07 02:52:16 UTC
HMDB IDHMDB0029746
Secondary Accession Numbers
  • HMDB29746
Metabolite Identification
Common Name3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole
Description3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole, also known as 3-amino-1,4-dimethyl-g-carboline or TRP-1, 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. Based on a literature review a significant number of articles have been published on 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole.
Structure
Data?1582753458
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 Weight211.2624
Monoisotopic Molecular Weight211.110947431
IUPAC Name1,4-dimethyl-5H-pyrido[4,3-b]indol-3-amine
Traditional Name1,4-dimethyl-5H-pyrido[4,3-b]indol-3-amine
CAS Registry Number62450-06-0
SMILES
CC1=C2C(NC3=CC=CC=C23)=C(C)C(N)=N1
InChI Identifier
InChI=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
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point252 - 262 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility61.72 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M-2H]-186.64730932474
DeepCCS[M+Na]+161.99730932474
AllCCS[M+H]+146.432859911
AllCCS[M+H-H2O]+142.132859911
AllCCS[M+NH4]+150.332859911
AllCCS[M+Na]+151.532859911
AllCCS[M-H]-152.032859911
AllCCS[M+Na-2H]-151.632859911
AllCCS[M+HCOO]-151.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indoleCC1=C2C(NC3=CC=CC=C23)=C(C)C(N)=N13436.1Standard polar33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indoleCC1=C2C(NC3=CC=CC=C23)=C(C)C(N)=N12255.5Standard non polar33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indoleCC1=C2C(NC3=CC=CC=C23)=C(C)C(N)=N12537.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,1TMS,isomer #1CC1=C(N[Si](C)(C)C)N=C(C)C2=C1[NH]C1=CC=CC=C122537.5Semi standard non polar33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,1TMS,isomer #1CC1=C(N[Si](C)(C)C)N=C(C)C2=C1[NH]C1=CC=CC=C122129.8Standard non polar33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,1TMS,isomer #2CC1=NC(N)=C(C)C2=C1C1=CC=CC=C1N2[Si](C)(C)C2507.9Semi standard non polar33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,1TMS,isomer #2CC1=NC(N)=C(C)C2=C1C1=CC=CC=C1N2[Si](C)(C)C2162.3Standard non polar33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,2TMS,isomer #1CC1=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(C)C2=C1[NH]C1=CC=CC=C122540.7Semi standard non polar33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,2TMS,isomer #1CC1=C(N([Si](C)(C)C)[Si](C)(C)C)N=C(C)C2=C1[NH]C1=CC=CC=C122275.4Standard non polar33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,2TMS,isomer #2CC1=NC(N[Si](C)(C)C)=C(C)C2=C1C1=CC=CC=C1N2[Si](C)(C)C2484.7Semi standard non polar33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,2TMS,isomer #2CC1=NC(N[Si](C)(C)C)=C(C)C2=C1C1=CC=CC=C1N2[Si](C)(C)C2190.5Standard non polar33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,3TMS,isomer #1CC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=C(C)C2=C1C1=CC=CC=C1N2[Si](C)(C)C2503.4Semi standard non polar33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,3TMS,isomer #1CC1=NC(N([Si](C)(C)C)[Si](C)(C)C)=C(C)C2=C1C1=CC=CC=C1N2[Si](C)(C)C2324.9Standard non polar33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,1TBDMS,isomer #1CC1=C(N[Si](C)(C)C(C)(C)C)N=C(C)C2=C1[NH]C1=CC=CC=C122761.9Semi standard non polar33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,1TBDMS,isomer #1CC1=C(N[Si](C)(C)C(C)(C)C)N=C(C)C2=C1[NH]C1=CC=CC=C122330.7Standard non polar33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,1TBDMS,isomer #2CC1=NC(N)=C(C)C2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C2734.3Semi standard non polar33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,1TBDMS,isomer #2CC1=NC(N)=C(C)C2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C2349.9Standard non polar33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,2TBDMS,isomer #1CC1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(C)C2=C1[NH]C1=CC=CC=C122898.5Semi standard non polar33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,2TBDMS,isomer #1CC1=C(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)N=C(C)C2=C1[NH]C1=CC=CC=C122672.7Standard non polar33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,2TBDMS,isomer #2CC1=NC(N[Si](C)(C)C(C)(C)C)=C(C)C2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C2837.3Semi standard non polar33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,2TBDMS,isomer #2CC1=NC(N[Si](C)(C)C(C)(C)C)=C(C)C2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C2614.6Standard non polar33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,3TBDMS,isomer #1CC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(C)C2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C2974.8Semi standard non polar33892256
3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole,3TBDMS,isomer #1CC1=NC(N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(C)C2=C1C1=CC=CC=C1N2[Si](C)(C)C(C)(C)C2903.9Standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole EI-B (Non-derivatized)splash10-01ox-6920000000-bc93105c1d081ec984b72017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole EI-B (Non-derivatized)splash10-01ox-6920000000-bc93105c1d081ec984b72018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dj-0930000000-36b5d2d7bf0b59d1b39b2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole 10V, Positive-QTOFsplash10-03di-0090000000-99d523d2d9b243b038af2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole 20V, Positive-QTOFsplash10-03di-0690000000-2b58ed661612ed6a86a72016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole 40V, Positive-QTOFsplash10-00kb-0900000000-47965f0b341d97a19de62016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole 10V, Negative-QTOFsplash10-03di-1090000000-f592d074259bb2ab388f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole 20V, Negative-QTOFsplash10-03di-1190000000-dd2a6c3bfecff2ce60232016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole 40V, Negative-QTOFsplash10-0006-9600000000-81184911da8b853890ff2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole 10V, Negative-QTOFsplash10-03di-0090000000-4dafdcd63f1115768fe92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole 20V, Negative-QTOFsplash10-03di-0090000000-bda0e0b196243b2f2b492021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole 40V, Negative-QTOFsplash10-0296-0910000000-9ff4ea4f5ec8709952f72021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole 10V, Positive-QTOFsplash10-03di-0090000000-151eb25ddf9df2d6bfbe2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole 20V, Positive-QTOFsplash10-03di-0090000000-151eb25ddf9df2d6bfbe2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Amino-1,4-dimethyl-5H-pyrido[4,3-b]indole 40V, Positive-QTOFsplash10-0007-0910000000-59be513918c2decfcf142021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB000947
KNApSAcK IDNot Available
Chemspider ID4447538
KEGG Compound IDC19306
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5284474
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1379871
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not 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. [PubMed:16943275 ]
  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. [PubMed:19939197 ]
  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. [PubMed:19546862 ]
  4. Mene P: Transient receptor potential channels in the kidney: calcium signaling, transport and beyond. J Nephrol. 2006 Jan-Feb;19(1):21-9. [PubMed:16523421 ]
  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. [PubMed:19842065 ]
  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. [PubMed:19879844 ]
  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. [PubMed:17434294 ]
  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. [PubMed:19429644 ]
  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. [PubMed:15272031 ]
  10. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .