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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:36:03 UTC

Update Date

2022-03-07 02:52:30 UTC

HMDB ID

HMDB0030311

Secondary Accession Numbers

HMDB30311

Metabolite Identification

Common Name

Harmine

Description

Harmine, also known as banisterine or leucoharmine, belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole. Harmine is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Harmine.

Structure

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

HRM
  Mrv0541 02241213442D          

 16 18  0  0  0  0            999 V2000
    2.0116   -1.1543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7566   -0.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3087    0.2434    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0537    1.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2467    1.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6947    0.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9497   -0.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2822   -0.6831    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3852   -0.1982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1922   -0.3697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1303    0.5864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6823    1.1995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4893    1.0280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7442    0.2434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5512    0.0719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8061   -0.7128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030311

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC=C2C(NC3=C2C=CN=C3C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3

> <INCHI_KEY>
BXNJHAXVSOCGBA-UHFFFAOYSA-N

> <FORMULA>
C13H12N2O

> <MOLECULAR_WEIGHT>
212.2472

> <EXACT_MASS>
212.094963016

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.45017546276285

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-methoxy-1-methyl-9H-pyrido[3,4-b]indole

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
1.8469121656666667

> <ALOGPS_LOGS>
-3.54

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.542985998251854

> <JCHEM_PKA_STRONGEST_BASIC>
6.153844207655581

> <JCHEM_POLAR_SURFACE_AREA>
37.91

> <JCHEM_REFRACTIVITY>
62.370000000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.13e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
harmine

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HRM                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       3.755  -2.155   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.279  -0.690   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       4.310   0.454   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       3.834   1.919   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.327   2.239   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.297   1.095   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.773  -0.370   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       0.527  -1.275   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -0.719  -0.370   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.225  -0.690   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.243   1.095   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.274   2.239   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.780   1.919   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.256   0.454   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.762   0.134   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -5.238  -1.331   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    2    6    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9   14                                                       
CONECT   11    6    9   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   10   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

COMPND    HMDB0030311
HETATM    1  C1  UNL     1       5.016   0.408  -0.433  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.869   1.234  -0.458  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.617   0.609  -0.338  1.00  0.00           C  
HETATM    4  C3  UNL     1       2.496  -0.758  -0.201  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.284  -1.410  -0.080  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.148  -0.626  -0.101  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.229   0.750  -0.238  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.460   1.359  -0.355  1.00  0.00           C  
HETATM    9  N1  UNL     1      -1.019   1.268  -0.228  1.00  0.00           N  
HETATM   10  C8  UNL     1      -1.909   0.250  -0.088  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.286   0.270  -0.024  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.981   1.573  -0.116  1.00  0.00           C  
HETATM   13  N2  UNL     1      -3.918  -0.897   0.119  1.00  0.00           N  
HETATM   14  C11 UNL     1      -3.256  -2.079   0.201  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.879  -2.101   0.137  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.178  -0.924  -0.009  1.00  0.00           C  
HETATM   17  H1  UNL     1       5.186  -0.064   0.554  1.00  0.00           H  
HETATM   18  H2  UNL     1       4.897  -0.397  -1.196  1.00  0.00           H  
HETATM   19  H3  UNL     1       5.873   1.056  -0.739  1.00  0.00           H  
HETATM   20  H4  UNL     1       3.414  -1.368  -0.186  1.00  0.00           H  
HETATM   21  H5  UNL     1       1.243  -2.491   0.026  1.00  0.00           H  
HETATM   22  H6  UNL     1       1.497   2.444  -0.461  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.256   2.270  -0.313  1.00  0.00           H  
HETATM   24  H8  UNL     1      -5.079   1.453  -0.089  1.00  0.00           H  
HETATM   25  H9  UNL     1      -3.642   2.178   0.757  1.00  0.00           H  
HETATM   26  H10 UNL     1      -3.653   2.049  -1.058  1.00  0.00           H  
HETATM   27  H11 UNL     1      -3.803  -2.995   0.315  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.372  -3.063   0.206  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   20
CONECT    5    6    6   21
CONECT    6    7   16
CONECT    7    8    8    9
CONECT    8   22
CONECT    9   10   23
CONECT   10   11   11   16
CONECT   11   12   13
CONECT   12   24   25   26
CONECT   13   14   14
CONECT   14   15   27
CONECT   15   16   16   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
6-Methoxyharman	ChEBI
7-Methoxy-1-methyl-9H-beta-carboline	ChEBI
Banisterine	ChEBI
Leucoharmine	ChEBI
Telepathine	ChEBI
Yageine	ChEBI
Yajeine	ChEBI
7-Methoxy-1-methyl-9H-b-carboline	Generator
7-Methoxy-1-methyl-9H-β-carboline	Generator
1-Methyl-7-methoxy-beta -carboline	HMDB
1-Methyl-7-methoxy-beta-carboline	HMDB
442-51-3 (FREE base)	HMDB
7-Methoxy-1-methyl-9H-pyrido(3,4-b)indole	HMDB
7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole	HMDB
7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole, 9ci	HMDB
Banisterin	HMDB
Garmin	HMDB
Harmin	HMDB
Harmin hydrochloride	HMDB
HRM	HMDB
Telepathien	HMDB
Telepathin	HMDB
Yagein	HMDB

Chemical Formula

C₁₃H₁₂N₂O

Average Molecular Weight

212.2472

Monoisotopic Molecular Weight

212.094963016

IUPAC Name

7-methoxy-1-methyl-9H-pyrido[3,4-b]indole

Traditional Name

harmine

CAS Registry Number

442-51-3

SMILES

COC1=CC=C2C(NC3=C2C=CN=C3C)=C1

InChI Identifier

InChI=1S/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3

InChI Key

BXNJHAXVSOCGBA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Harmala alkaloids

Sub Class

Not Available

Direct Parent

Harmala alkaloids

Alternative Parents

Substituents

Harman
Beta-carboline
Pyridoindole
Indole
Indole or derivatives
Anisole
Methylpyridine
Alkyl aryl ether
Benzenoid
Pyridine
Heteroaromatic compound
Pyrrole
Ether
Azacycle
Organoheterocyclic compound
Organopnictogen compound
Organic nitrogen compound
Organic oxygen compound
Hydrocarbon derivative
Organonitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

harmala alkaloid (CHEBI:28121 )
Indole alkaloids (C06538 )
an alkaloid (CPD-9940 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0030311)
Cell membrane (HMDB: HMDB0030311)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030311)

Source

Exogenous

Exogenous (HMDB: HMDB0030311)

Food

Food (HMDB: HMDB0030311)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Endogenous (HMDB: HMDB0030311)

Plant

Plant (HMDB: HMDB0030311)

Process

Not Available

Role

Industrial application

Pharmaceutical industry

Pharmaceutical (HMDB: HMDB0030311)

Manufacturing industry

Material processing agent

Coloring agent

Fluorescent agent

Hallucinogen (HMDB: HMDB0030311)

Biological role

Depressant (HMDB: HMDB0030311)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	264 - 265 °C	Not Available
Boiling Point	421.40 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	2.68 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.56	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	145.275	30932474
[M+H]+	MetCCS_train_pos	146.033	30932474
[M+H]+	Not Available	144.507	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001371

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.061 g/L	ALOGPS
logP	3.05	ALOGPS
logP	1.85	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	13.54	ChemAxon
pKa (Strongest Basic)	6.15	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.91 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	62.37 m³·mol⁻¹	ChemAxon
Polarizability	23.45 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]+	150.0	31661259
DarkChem	[M-H]-	150.595	31661259
DeepCCS	[M+H]+	151.4	30932474
DeepCCS	[M-H]-	149.005	30932474
DeepCCS	[M-2H]-	182.091	30932474
DeepCCS	[M+Na]+	157.421	30932474
AllCCS	[M+H]+	146.4	32859911
AllCCS	[M+H-H2O]+	142.1	32859911
AllCCS	[M+NH4]+	150.4	32859911
AllCCS	[M+Na]+	151.6	32859911
AllCCS	[M-H]-	151.9	32859911
AllCCS	[M+Na-2H]-	151.6	32859911
AllCCS	[M+HCOO]-	151.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Harmine	COC1=CC=C2C(NC3=C2C=CN=C3C)=C1	2697.4	Standard polar	33892256
Harmine	COC1=CC=C2C(NC3=C2C=CN=C3C)=C1	2282.3	Standard non polar	33892256
Harmine	COC1=CC=C2C(NC3=C2C=CN=C3C)=C1	2239.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Harmine,1TMS,isomer #1	COC1=CC=C2C3=CC=NC(C)=C3N([Si](C)(C)C)C2=C1	2434.1	Semi standard non polar	33892256
Harmine,1TMS,isomer #1	COC1=CC=C2C3=CC=NC(C)=C3N([Si](C)(C)C)C2=C1	2108.3	Standard non polar	33892256
Harmine,1TBDMS,isomer #1	COC1=CC=C2C3=CC=NC(C)=C3N([Si](C)(C)C(C)(C)C)C2=C1	2597.1	Semi standard non polar	33892256
Harmine,1TBDMS,isomer #1	COC1=CC=C2C3=CC=NC(C)=C3N([Si](C)(C)C(C)(C)C)C2=C1	2304.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Harmine GC-MS (Non-derivatized) - 70eV, Positive	splash10-0i00-0910000000-7d7913e8c62ca2fc405f	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Harmine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Harmine 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 - Harmine LC-ESI-QTOF , negative-QTOF	splash10-03di-0190000000-fa0446e989509658da3d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Harmine LC-ESI-QTOF , negative-QTOF	splash10-0002-0910000000-4a6e6c341c4868149774	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Harmine LC-ESI-QTOF , negative-QTOF	splash10-0002-0900000000-8d47230f745bacac3927	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Harmine LC-ESI-QTOF , negative-QTOF	splash10-00kb-0900000000-16e41b0926f6f19e8e38	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Harmine LC-ESI-QTOF , negative-QTOF	splash10-00kb-0900000000-8ad2d2db9ac2e4e33f2a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Harmine LC-ESI-QTOF , negative-QTOF	splash10-03dj-0980000000-f76e1f1ebc0a34cf9e19	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Harmine LC-ESI-QTOF , negative-QTOF	splash10-0002-0900000000-10a7486ab11a55848f36	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Harmine LC-ESI-QTOF , negative-QTOF	splash10-014j-0900000000-f96154ced990a53da1ed	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Harmine LC-ESI-QTOF , positive-QTOF	splash10-03di-0090000000-39de68994dd0d4e10b08	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Harmine LC-ESI-QTOF , positive-QTOF	splash10-03di-0190000000-4eb0eb565ba056865aa6	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Harmine LC-ESI-QTOF , positive-QTOF	splash10-006t-0920000000-e68ee06c7ad898d448b0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Harmine LC-ESI-QTOF , positive-QTOF	splash10-00di-0900000000-996c89900776affe7b42	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Harmine LC-ESI-QTOF , positive-QTOF	splash10-01b9-0900000000-8b5053cf47cac449fab7	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Harmine LC-ESI-QTOF , positive-QTOF	splash10-03di-0190000000-c155ccc223856b24d591	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Harmine LC-ESI-QTOF , positive-QTOF	splash10-01ot-0950000000-012b0b00f2690f9f975d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Harmine LC-ESI-QTOF , positive-QTOF	splash10-00xr-0900000000-87c0ba2a9de84a712604	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Harmine , positive-QTOF	splash10-00di-0910000000-c3bf098f88a09ca6c88a	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Harmine , positive-QTOF	splash10-00di-0920000000-b2bbb79b7783c3ddbfcb	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Harmine 10V, Positive-QTOF	splash10-03di-0090000000-16c78e24d1360e57d40f	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Harmine 10V, Positive-QTOF	splash10-03di-0190000000-d370357f0aac7ede48b9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Harmine 20V, Positive-QTOF	splash10-03di-0390000000-0c52b2b93b9768e8c0eb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Harmine 40V, Positive-QTOF	splash10-0pc3-0900000000-4430786ab672a4a37985	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Harmine 10V, Negative-QTOF	splash10-03di-0090000000-aaa1924bac5dcced18a9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Harmine 20V, Negative-QTOF	splash10-03di-0390000000-c91a13bc98f3113246eb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Harmine 40V, Negative-QTOF	splash10-0002-0900000000-2eec3308c9ff2fdb800c	2016-08-03	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

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

DB07919

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Harmine

METLIN ID

Not Available

PubChem Compound

5280953

PDB ID

HRM

ChEBI ID

28121

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1249111

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Gambelunghe C, Aroni K, Rossi R, Moretti L, Bacci M: Identification of N,N-dimethyltryptamine and beta-carbolines in psychotropic ayahuasca beverage. Biomed Chromatogr. 2008 Oct;22(10):1056-9. doi: 10.1002/bmc.1023. [PubMed:18506697 ]
Yonezawa T, Lee JW, Hibino A, Asai M, Hojo H, Cha BY, Teruya T, Nagai K, Chung UI, Yagasaki K, Woo JT: Harmine promotes osteoblast differentiation through bone morphogenetic protein signaling. Biochem Biophys Res Commun. 2011 Jun 3;409(2):260-5. doi: 10.1016/j.bbrc.2011.05.001. Epub 2011 May 6. [PubMed:21570953 ]
Hamsa TP, Kuttan G: Harmine inhibits tumour specific neo-vessel formation by regulating VEGF, MMP, TIMP and pro-inflammatory mediators both in vivo and in vitro. Eur J Pharmacol. 2010 Dec 15;649(1-3):64-73. doi: 10.1016/j.ejphar.2010.09.010. Epub 2010 Sep 19. [PubMed:20858484 ]
Reus GZ, Stringari RB, de Souza B, Petronilho F, Dal-Pizzol F, Hallak JE, Zuardi AW, Crippa JA, Quevedo J: Harmine and imipramine promote antioxidant activities in prefrontal cortex and hippocampus. Oxid Med Cell Longev. 2010 Sep-Oct;3(5):325-31. Epub 2010 Sep 1. [PubMed:21150338 ]
Carpentier RG: The effect of harmine on the action potential of the guinea-pig atrial muscle depends on the external calcium concentration. Br J Pharmacol. 1981 Oct;74(2):415-8. [PubMed:7317690 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Harmine (HMDB0030311)

MOL for HMDB0030311 (Harmine)

3D MOL for HMDB0030311 (Harmine)

3D SDF for HMDB0030311 (Harmine)

3D-SDF for HMDB0030311 (Harmine)

PDB for HMDB0030311 (Harmine)

3D PDB for HMDB0030311 (Harmine)

SMILES for HMDB0030311 (Harmine)

INCHI for HMDB0030311 (Harmine)

Structure for HMDB0030311 (Harmine)

3D Structure for HMDB0030311 (Harmine)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra