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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2009-07-25 00:01:33 UTC

Update Date

2023-02-21 17:17:49 UTC

HMDB ID

HMDB0012488

Secondary Accession Numbers

HMDB12488

Metabolite Identification

Common Name

1,2,3,4-Tetrahydro-beta-carboline

Description

Tetrahydro-b-carbolines (THbCs)are potential neuroactive alkaloids found in chocolate and cocoa. The formation of 1,2,3,4-tetrahydro-/3-carbolines (THBCs), via the Pictet-Spengler condensation of tryptamines with formaldehyde, has been demonstrated repeatedly in incubations of various mammalian tissues containing added indolethylamine substrate and the methyl donors .5-methyltetrahydrofolate (5-MTHF) or S-adenosylmethionine(SAM). It is concluded that the formation of these THBCs is an artifact produced by the enzymatic liberation of formaldehyde from the methyl donors and the subsequent non-enzymatic condensation of this formaldehyde with the indole substrates. The formation of THBCs in vivo has thus remained a point of contention. (PMID: 7213417 ). 1,2,3,4-Tetrahydro-beta-carboline is a biomarker for the consumption of beer

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      19.951 -26.962   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.285 -27.732   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.619 -26.962   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.619 -25.422   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.285 -24.652   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      19.951 -25.422   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      24.083 -24.946   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      24.988 -26.192   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      26.519 -26.352   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      27.146 -27.759   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      26.240 -29.005   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.710 -28.844   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.083 -27.437   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13    3    8   12                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   30    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,2,3,4-Tetrahydro-b-carboline	Generator
1,2,3,4-Tetrahydro-β-carboline	Generator
1,2,3,4-Tetrahydronorharmane	HMDB
THBC	HMDB
Tryptoline hydrochloride	MeSH, HMDB
THbetaC	MeSH, HMDB
Tetrahydronorharmane	MeSH, HMDB
9H-1,2,3,4-tetrahydropyrido(3,4-b)Indole	MeSH, HMDB
Noreleagnine	MeSH, HMDB
tetrahydro-beta-Carboline	MeSH, HMDB
Tryptoline monohydrochloride	MeSH, HMDB
Triptoline	MeSH, HMDB
1,2,3,4-Tetrahydro-beta-carboline	MeSH
Tryptoline	MeSH

Chemical Formula

C₁₁H₁₂N₂

Average Molecular Weight

172.2264

Monoisotopic Molecular Weight

172.100048394

IUPAC Name

1H,2H,3H,4H,9H-pyrido[3,4-b]indole

Traditional Name

tryptoline

CAS Registry Number

Not Available

SMILES

C1CC2=C(CN1)NC1=C2C=CC=C1

InChI Identifier

InChI=1S/C11H12N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-4,12-13H,5-7H2

InChI Key

CFTOTSJVQRFXOF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Beta carbolines

Alternative Parents

Substituents

Beta-carboline
3-alkylindole
Indole
Aralkylamine
Benzenoid
Heteroaromatic compound
Pyrrole
Azacycle
Secondary amine
Secondary aliphatic amine
Organopnictogen compound
Organonitrogen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Endogenous (HMDB: HMDB0012488)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.43 g/L	ALOGPS
logP	1.31	ALOGPS
logP	1.59	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	16.46	ChemAxon
pKa (Strongest Basic)	9.01	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	27.82 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	53.58 m³·mol⁻¹	ChemAxon
Polarizability	19.62 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	137.868	31661259
DarkChem	[M-H]-	136.823	31661259
DeepCCS	[M+H]+	135.857	30932474
DeepCCS	[M-H]-	133.177	30932474
DeepCCS	[M-2H]-	168.966	30932474
DeepCCS	[M+Na]+	144.504	30932474
AllCCS	[M+H]+	137.1	32859911
AllCCS	[M+H-H2O]+	132.5	32859911
AllCCS	[M+NH4]+	141.3	32859911
AllCCS	[M+Na]+	142.5	32859911
AllCCS	[M-H]-	140.8	32859911
AllCCS	[M+Na-2H]-	140.9	32859911
AllCCS	[M+HCOO]-	141.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
1,2,3,4-Tetrahydro-beta-carboline	C1CC2=C(CN1)NC1=C2C=CC=C1	2940.9	Standard polar	33892256
1,2,3,4-Tetrahydro-beta-carboline	C1CC2=C(CN1)NC1=C2C=CC=C1	1862.9	Standard non polar	33892256
1,2,3,4-Tetrahydro-beta-carboline	C1CC2=C(CN1)NC1=C2C=CC=C1	1951.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
1,2,3,4-Tetrahydro-beta-carboline,1TMS,isomer #1	C[Si](C)(C)N1CCC2=C(C1)[NH]C1=CC=CC=C21	2071.0	Semi standard non polar	33892256
1,2,3,4-Tetrahydro-beta-carboline,1TMS,isomer #1	C[Si](C)(C)N1CCC2=C(C1)[NH]C1=CC=CC=C21	1919.5	Standard non polar	33892256
1,2,3,4-Tetrahydro-beta-carboline,1TMS,isomer #1	C[Si](C)(C)N1CCC2=C(C1)[NH]C1=CC=CC=C21	2411.6	Standard polar	33892256
1,2,3,4-Tetrahydro-beta-carboline,1TMS,isomer #2	C[Si](C)(C)N1C2=C(CCNC2)C2=CC=CC=C21	1995.8	Semi standard non polar	33892256
1,2,3,4-Tetrahydro-beta-carboline,1TMS,isomer #2	C[Si](C)(C)N1C2=C(CCNC2)C2=CC=CC=C21	1755.9	Standard non polar	33892256
1,2,3,4-Tetrahydro-beta-carboline,1TMS,isomer #2	C[Si](C)(C)N1C2=C(CCNC2)C2=CC=CC=C21	2316.2	Standard polar	33892256
1,2,3,4-Tetrahydro-beta-carboline,2TMS,isomer #1	C[Si](C)(C)N1CCC2=C(C1)N([Si](C)(C)C)C1=CC=CC=C21	2054.8	Semi standard non polar	33892256
1,2,3,4-Tetrahydro-beta-carboline,2TMS,isomer #1	C[Si](C)(C)N1CCC2=C(C1)N([Si](C)(C)C)C1=CC=CC=C21	2041.7	Standard non polar	33892256
1,2,3,4-Tetrahydro-beta-carboline,2TMS,isomer #1	C[Si](C)(C)N1CCC2=C(C1)N([Si](C)(C)C)C1=CC=CC=C21	2232.2	Standard polar	33892256
1,2,3,4-Tetrahydro-beta-carboline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC2=C(C1)[NH]C1=CC=CC=C21	2317.1	Semi standard non polar	33892256
1,2,3,4-Tetrahydro-beta-carboline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC2=C(C1)[NH]C1=CC=CC=C21	2147.1	Standard non polar	33892256
1,2,3,4-Tetrahydro-beta-carboline,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC2=C(C1)[NH]C1=CC=CC=C21	2617.7	Standard polar	33892256
1,2,3,4-Tetrahydro-beta-carboline,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C2=C(CCNC2)C2=CC=CC=C21	2220.2	Semi standard non polar	33892256
1,2,3,4-Tetrahydro-beta-carboline,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C2=C(CCNC2)C2=CC=CC=C21	1989.8	Standard non polar	33892256
1,2,3,4-Tetrahydro-beta-carboline,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1C2=C(CCNC2)C2=CC=CC=C21	2421.5	Standard polar	33892256
1,2,3,4-Tetrahydro-beta-carboline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC2=C(C1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21	2473.8	Semi standard non polar	33892256
1,2,3,4-Tetrahydro-beta-carboline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC2=C(C1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21	2477.3	Standard non polar	33892256
1,2,3,4-Tetrahydro-beta-carboline,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N1CCC2=C(C1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21	2488.9	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline GC-MS (Non-derivatized) - 70eV, Positive	splash10-0596-0900000000-0c12ea5ede1ecce0b8a0	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline LC-ESI-qTof , Positive-QTOF	splash10-0006-3900000000-59256f2013af0388b609	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline , positive-QTOF	splash10-0006-0900000000-298d086f2db7bfb96c7f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline , positive-QTOF	splash10-0006-3900000000-59256f2013af0388b609	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline 35V, Positive-QTOF	splash10-0006-0900000000-0e95cd13061c8268d13d	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline 10V, Positive-QTOF	splash10-00di-0900000000-d1cf77f85d424207ea20	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline 20V, Positive-QTOF	splash10-006x-0900000000-fa3e868e9ca6a59d5b91	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline 40V, Positive-QTOF	splash10-0560-0900000000-76a12e37b5faa4cbb856	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline 10V, Negative-QTOF	splash10-00di-0900000000-2305b865b13eae850bbb	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline 20V, Negative-QTOF	splash10-00di-0900000000-d58681edbdcc31aced92	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline 40V, Negative-QTOF	splash10-0596-0900000000-3e4b9943ce69d390f2aa	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline 10V, Positive-QTOF	splash10-00di-0900000000-ff5f70dda818b9673030	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline 20V, Positive-QTOF	splash10-00di-0900000000-1b2e7c8ce9fa45740ef0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline 40V, Positive-QTOF	splash10-00bc-2900000000-f5466bd5eff0535cb5b2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline 10V, Negative-QTOF	splash10-00di-0900000000-84df739a23ca1993145c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline 20V, Negative-QTOF	splash10-00di-0900000000-84df739a23ca1993145c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 1,2,3,4-Tetrahydro-beta-carboline 40V, Negative-QTOF	splash10-0006-0900000000-234e77ff29e2c2061761	2021-09-23	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029095

KNApSAcK ID

C00052418

Chemspider ID

96979

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

107838

PDB ID

Not Available

ChEBI ID

100417

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barker SA, Harrison RE, Monti JA, Brown GB, Christian ST: Identification and quantification of 1,2,3,4-tetrahydro-beta-carboline, 2-methyl-1,2,3,4-tetrahydro-beta-carboline, and 6-methoxy-1,2,3,4-tetrahydro-beta-carboline as in vivo constituents of rat brain and adrenal gland. Biochem Pharmacol. 1981 Jan 1;30(1):9-17. [PubMed:7213417 ]

Showing metabocard for 1,2,3,4-Tetrahydro-beta-carboline (HMDB0012488)

MOL for HMDB0012488 (1,2,3,4-Tetrahydro-beta-carboline)

3D MOL for HMDB0012488 (1,2,3,4-Tetrahydro-beta-carboline)

3D SDF for HMDB0012488 (1,2,3,4-Tetrahydro-beta-carboline)

3D-SDF for HMDB0012488 (1,2,3,4-Tetrahydro-beta-carboline)

PDB for HMDB0012488 (1,2,3,4-Tetrahydro-beta-carboline)

3D PDB for HMDB0012488 (1,2,3,4-Tetrahydro-beta-carboline)

SMILES for HMDB0012488 (1,2,3,4-Tetrahydro-beta-carboline)

INCHI for HMDB0012488 (1,2,3,4-Tetrahydro-beta-carboline)

Structure for HMDB0012488 (1,2,3,4-Tetrahydro-beta-carboline)

3D Structure for HMDB0012488 (1,2,3,4-Tetrahydro-beta-carboline)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra