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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 17:42:43 UTC

Update Date

2023-02-21 17:17:01 UTC

HMDB ID

HMDB0004369

Secondary Accession Numbers

HMDB04369

Metabolite Identification

Common Name

N-Methylserotonin

Description

N-Methylserotonin, also known as lopac-m-1514, belongs to the class of organic compounds known as serotonins. Serotonins are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5. Chemically, it is a derivative of serotonin in which a methyl group resides at its alkyl amine. N-Methylserotonin is a very strong basic compound (based on its pKa). N-methylserotonin and S-adenosylhomocysteine can be biosynthesized from serotonin and S-adenosylmethionine through the action of the enzyme indolethylamine N-methyltransferase. These include the plants, Actaea racemosa (black cohosh) and Zanthoxylum piperitum, the Green and Golden Bell Frog, Litoria aurea, and Amanita mushrooms. The compound binds to several serotonin receptors, including the 5-HT7 and 5-HT1A receptors, with high affinity (IC50 ≤ 2 nM) and selectivity, and displays agonist activity; besides its direct interaction with the serotonin receptors, N-methylserotonin also acts as a selective serotonin reuptake inhibitor. N-Methylserotonin is not scheduled at the federal level in the United States, but could be considered an analog (of bufotenin), in which case, sales or possession intended for human consumption could be prosecuted under the Federal Analog Act. In humans, N-methylserotonin is involved in tryptophan metabolism. Outside of the human body, N-Methylserotonin has been detected, but not quantified in, citrus. This could make N-methylserotonin a potential biomarker for the consumption of these foods. N-Methylserotonin is a tryptamine alkaloid. Florida N-Methylserotonin is a Schedule I controlled substance in the state of Florida making it illegal to buy, sell, or possess in Florida. It is also called Nω-methylserotonin (Nω-methyl-5-hydroxytryptamine) to distinguish it from tryptamine-derived compounds in which a methyl group is bonded to the nitrogen atom of the indole group.

Structure

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

  Mrv0541 02231219562D          

 14 15  0  0  0  0            999 V2000
   27.4306  -14.1256    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.6746  -12.5482    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.3547  -15.6145    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   31.4183  -13.3323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.6110  -13.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4819  -12.3780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1451  -14.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5741  -15.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3547  -14.2867    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5741  -14.5381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.8362  -14.9506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8596  -14.1256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.1451  -15.3631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8596  -15.7756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  1  0  0  0  0
  2  4  1  0  0  0  0
  2  6  1  0  0  0  0
  3  8  1  0  0  0  0
  3 11  1  0  0  0  0
  4  5  1  0  0  0  0
  5  9  1  0  0  0  0
  7 12  2  0  0  0  0
  7 13  1  0  0  0  0
  8 10  2  0  0  0  0
  8 14  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 10 12  1  0  0  0  0
 13 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0004369

> <DATABASE_NAME>
hmdb

> <SMILES>
CNCCC1=CNC2=C1C=C(O)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C11H14N2O/c1-12-5-4-8-7-13-11-3-2-9(14)6-10(8)11/h2-3,6-7,12-14H,4-5H2,1H3

> <INCHI_KEY>
ASUSBMNYRHGZIG-UHFFFAOYSA-N

> <FORMULA>
C11H14N2O

> <MOLECULAR_WEIGHT>
190.2417

> <EXACT_MASS>
190.11061308

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
21.400403757787508

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[2-(methylamino)ethyl]-1H-indol-5-ol

> <ALOGPS_LOGP>
1.55

> <JCHEM_LOGP>
0.6882991081279496

> <ALOGPS_LOGS>
-2.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
18.221046372810616

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.450406133402005

> <JCHEM_PKA_STRONGEST_BASIC>
10.441770003332964

> <JCHEM_POLAR_SURFACE_AREA>
48.05

> <JCHEM_REFRACTIVITY>
57.12840000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-methylserotonin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      51.204 -26.368   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0      59.126 -23.423   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0      56.662 -29.147   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0      58.647 -24.887   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      57.141 -25.205   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      60.633 -23.106   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      52.538 -27.138   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      55.205 -28.678   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      56.662 -26.669   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      55.205 -27.138   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      57.561 -27.908   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      53.871 -26.368   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      52.538 -28.678   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      53.871 -29.448   0.000  0.00  0.00           C+0
CONECT    1    7                                                            
CONECT    2    4    6                                                       
CONECT    3    8   11                                                       
CONECT    4    2    5                                                       
CONECT    5    4    9                                                       
CONECT    6    2                                                            
CONECT    7    1   12   13                                                  
CONECT    8    3   10   14                                                  
CONECT    9    5   10   11                                                  
CONECT   10    8    9   12                                                  
CONECT   11    3    9                                                       
CONECT   12    7   10                                                       
CONECT   13    7   14                                                       
CONECT   14    8   13                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

COMPND    HMDB0004369
HETATM    1  C1  UNL     1       3.716   0.225  -0.246  1.00  0.00           C  
HETATM    2  N1  UNL     1       2.516  -0.122  -0.946  1.00  0.00           N  
HETATM    3  C2  UNL     1       1.821  -1.249  -0.385  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.225  -0.963   0.966  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.237   0.154   0.902  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.396   1.462   1.324  1.00  0.00           C  
HETATM    7  N2  UNL     1      -0.740   2.151   1.089  1.00  0.00           N  
HETATM    8  C6  UNL     1      -1.668   1.340   0.518  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.965   1.583   0.099  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.664   0.531  -0.454  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.062  -0.704  -0.571  1.00  0.00           C  
HETATM   12  O1  UNL     1      -3.780  -1.766  -1.134  1.00  0.00           O  
HETATM   13  C10 UNL     1      -1.772  -0.948  -0.156  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.052   0.101   0.405  1.00  0.00           C  
HETATM   15  H1  UNL     1       4.067  -0.567   0.452  1.00  0.00           H  
HETATM   16  H2  UNL     1       4.522   0.364  -0.996  1.00  0.00           H  
HETATM   17  H3  UNL     1       3.603   1.214   0.268  1.00  0.00           H  
HETATM   18  H4  UNL     1       2.673  -0.205  -1.966  1.00  0.00           H  
HETATM   19  H5  UNL     1       0.983  -1.502  -1.064  1.00  0.00           H  
HETATM   20  H6  UNL     1       2.529  -2.100  -0.350  1.00  0.00           H  
HETATM   21  H7  UNL     1       1.992  -0.707   1.726  1.00  0.00           H  
HETATM   22  H8  UNL     1       0.761  -1.907   1.315  1.00  0.00           H  
HETATM   23  H9  UNL     1       1.321   1.817   1.767  1.00  0.00           H  
HETATM   24  H10 UNL     1      -0.858   3.160   1.322  1.00  0.00           H  
HETATM   25  H11 UNL     1      -3.422   2.550   0.196  1.00  0.00           H  
HETATM   26  H12 UNL     1      -4.699   0.668  -0.801  1.00  0.00           H  
HETATM   27  H13 UNL     1      -3.400  -2.680  -1.244  1.00  0.00           H  
HETATM   28  H14 UNL     1      -1.282  -1.896  -0.235  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3   18
CONECT    3    4   19   20
CONECT    4    5   21   22
CONECT    5    6    6   14
CONECT    6    7   23
CONECT    7    8   24
CONECT    8    9    9   14
CONECT    9   10   25
CONECT   10   11   11   26
CONECT   11   12   13
CONECT   12   27
CONECT   13   14   14   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
N-Methylserotonin oxalate salt	HMDB
3-(2-(Methylamino)ethyl)-1H-indol-5-ol	HMDB
3-[2-(Methylamino)ethyl]-1H-indol-5-ol	HMDB
Lopac-m-1514	HMDB

Chemical Formula

C₁₁H₁₄N₂O

Average Molecular Weight

190.2417

Monoisotopic Molecular Weight

190.11061308

IUPAC Name

3-[2-(methylamino)ethyl]-1H-indol-5-ol

Traditional Name

N-methylserotonin

CAS Registry Number

1134-01-6

SMILES

CNCCC1=CNC2=C1C=C(O)C=C2

InChI Identifier

InChI=1S/C11H14N2O/c1-12-5-4-8-7-13-11-3-2-9(14)6-10(8)11/h2-3,6-7,12-14H,4-5H2,1H3

InChI Key

ASUSBMNYRHGZIG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as serotonins. Serotonins are compounds containing a serotonin moiety, which consists of an indole that bears an aminoethyl a position 2 and a hydroxyl group at position 5.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

Serotonins

Alternative Parents

Substituents

Serotonin
Hydroxyindole
3-alkylindole
Indole
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
Substituted pyrrole
Pyrrole
Heteroaromatic compound
Secondary aliphatic amine
Secondary amine
Azacycle
Amine
Hydrocarbon derivative
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

phenols (CHEBI:48294 )
tryptamines (CHEBI:48294 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Cytoplasm (HMDB: HMDB0004369)

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0004369)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0004369)

Source

Endogenous

Endogenous (HMDB: HMDB0004369)

Plant

Plant (HMDB: HMDB0004369)

Exogenous

Food

Food (HMDB: HMDB0004369)

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Tryptophan Metabolism (PathBank: SMP0063693)
Tryptophan Metabolism (HMDB: HMDB0004369)

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	0.75 g/L	ALOGPS
logP	1.55	ALOGPS
logP	0.69	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	9.45	ChemAxon
pKa (Strongest Basic)	10.44	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	48.05 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	57.13 m³·mol⁻¹	ChemAxon
Polarizability	21.4 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	142.864	31661259
DarkChem	[M-H]-	141.673	31661259
DeepCCS	[M+H]+	142.796	30932474
DeepCCS	[M-H]-	138.968	30932474
DeepCCS	[M-2H]-	176.396	30932474
DeepCCS	[M+Na]+	151.935	30932474
AllCCS	[M+H]+	142.4	32859911
AllCCS	[M+H-H2O]+	138.2	32859911
AllCCS	[M+NH4]+	146.4	32859911
AllCCS	[M+Na]+	147.6	32859911
AllCCS	[M-H]-	145.6	32859911
AllCCS	[M+Na-2H]-	146.0	32859911
AllCCS	[M+HCOO]-	146.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	2.62 minutes	32390414
Predicted by Siyang on May 30, 2022	9.2151 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.01 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	121.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	668.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	266.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	93.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	159.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	99.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	285.2 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	238.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	721.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	611.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	142.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	857.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	194.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	201.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	708.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	430.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	158.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Methylserotonin	CNCCC1=CNC2=C1C=C(O)C=C2	3161.4	Standard polar	33892256
N-Methylserotonin	CNCCC1=CNC2=C1C=C(O)C=C2	2049.5	Standard non polar	33892256
N-Methylserotonin	CNCCC1=CNC2=C1C=C(O)C=C2	2133.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Methylserotonin,1TMS,isomer #1	CNCCC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12	1986.2	Semi standard non polar	33892256
N-Methylserotonin,1TMS,isomer #2	CN(CCC1=C[NH]C2=CC=C(O)C=C12)[Si](C)(C)C	2215.7	Semi standard non polar	33892256
N-Methylserotonin,1TMS,isomer #3	CNCCC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12	2056.9	Semi standard non polar	33892256
N-Methylserotonin,2TMS,isomer #1	CN(CCC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12)[Si](C)(C)C	2220.1	Semi standard non polar	33892256
N-Methylserotonin,2TMS,isomer #1	CN(CCC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12)[Si](C)(C)C	2285.8	Standard non polar	33892256
N-Methylserotonin,2TMS,isomer #1	CN(CCC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12)[Si](C)(C)C	2362.3	Standard polar	33892256
N-Methylserotonin,2TMS,isomer #2	CNCCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12	2041.7	Semi standard non polar	33892256
N-Methylserotonin,2TMS,isomer #2	CNCCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12	2139.9	Standard non polar	33892256
N-Methylserotonin,2TMS,isomer #2	CNCCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12	2265.6	Standard polar	33892256
N-Methylserotonin,2TMS,isomer #3	CN(CCC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)[Si](C)(C)C	2296.0	Semi standard non polar	33892256
N-Methylserotonin,2TMS,isomer #3	CN(CCC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)[Si](C)(C)C	2368.1	Standard non polar	33892256
N-Methylserotonin,2TMS,isomer #3	CN(CCC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)[Si](C)(C)C	2391.5	Standard polar	33892256
N-Methylserotonin,3TMS,isomer #1	CN(CCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)[Si](C)(C)C	2293.6	Semi standard non polar	33892256
N-Methylserotonin,3TMS,isomer #1	CN(CCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)[Si](C)(C)C	2305.9	Standard non polar	33892256
N-Methylserotonin,3TMS,isomer #1	CN(CCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)[Si](C)(C)C	2246.5	Standard polar	33892256
N-Methylserotonin,1TBDMS,isomer #1	CNCCC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	2252.0	Semi standard non polar	33892256
N-Methylserotonin,1TBDMS,isomer #2	CN(CCC1=C[NH]C2=CC=C(O)C=C12)[Si](C)(C)C(C)(C)C	2462.8	Semi standard non polar	33892256
N-Methylserotonin,1TBDMS,isomer #3	CNCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12	2305.2	Semi standard non polar	33892256
N-Methylserotonin,2TBDMS,isomer #1	CN(CCC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)[Si](C)(C)C(C)(C)C	2710.0	Semi standard non polar	33892256
N-Methylserotonin,2TBDMS,isomer #1	CN(CCC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)[Si](C)(C)C(C)(C)C	2733.2	Standard non polar	33892256
N-Methylserotonin,2TBDMS,isomer #1	CN(CCC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)[Si](C)(C)C(C)(C)C	2585.5	Standard polar	33892256
N-Methylserotonin,2TBDMS,isomer #2	CNCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	2504.2	Semi standard non polar	33892256
N-Methylserotonin,2TBDMS,isomer #2	CNCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	2583.3	Standard non polar	33892256
N-Methylserotonin,2TBDMS,isomer #2	CNCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12	2468.6	Standard polar	33892256
N-Methylserotonin,2TBDMS,isomer #3	CN(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)[Si](C)(C)C(C)(C)C	2723.1	Semi standard non polar	33892256
N-Methylserotonin,2TBDMS,isomer #3	CN(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)[Si](C)(C)C(C)(C)C	2792.8	Standard non polar	33892256
N-Methylserotonin,2TBDMS,isomer #3	CN(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)[Si](C)(C)C(C)(C)C	2572.4	Standard polar	33892256
N-Methylserotonin,3TBDMS,isomer #1	CN(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)[Si](C)(C)C(C)(C)C	2953.0	Semi standard non polar	33892256
N-Methylserotonin,3TBDMS,isomer #1	CN(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)[Si](C)(C)C(C)(C)C	2930.1	Standard non polar	33892256
N-Methylserotonin,3TBDMS,isomer #1	CN(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)[Si](C)(C)C(C)(C)C	2572.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Methylserotonin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-514cf662a4e6c5a603df	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Methylserotonin GC-MS (1 TMS) - 70eV, Positive	splash10-0006-9120000000-4c9438c3246e1f92d1f5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Methylserotonin 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylserotonin 10V, Positive-QTOF	splash10-01ox-0900000000-646686588892f9e597f5	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylserotonin 20V, Positive-QTOF	splash10-03dl-1900000000-a768b9399c8fcac6cd0e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylserotonin 40V, Positive-QTOF	splash10-01q9-2900000000-543fe5365e1fa682b60e	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylserotonin 10V, Negative-QTOF	splash10-000i-0900000000-b4a2e8f1bf6e3e782690	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylserotonin 20V, Negative-QTOF	splash10-000i-0900000000-970029b3b4e6dd32e53a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylserotonin 40V, Negative-QTOF	splash10-001i-2900000000-9851a5693e2c284d3b9d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylserotonin 10V, Positive-QTOF	splash10-01ox-0900000000-068fac34efa1b5ba779c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylserotonin 20V, Positive-QTOF	splash10-03di-0900000000-46a702a381d3892e40b4	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylserotonin 40V, Positive-QTOF	splash10-0f8c-2900000000-d17d6394f323b90f889c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylserotonin 10V, Negative-QTOF	splash10-000i-0900000000-737a601f9d97628ca508	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylserotonin 20V, Negative-QTOF	splash10-0019-0900000000-58467315e6d4795f2488	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Methylserotonin 40V, Negative-QTOF	splash10-001i-2900000000-cdd5d680769ece6297e4	2021-09-24	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

Cytoplasm

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Tryptophan metabolism	Not Available

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

FDB017273

KNApSAcK ID

Not Available

Chemspider ID

132989

KEGG Compound ID

C06212

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

48294

Food Biomarker Ontology

Not Available

VMH ID

NMTHSRTN

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Somei, Masanori; Yamada, Fumio; Kurauchi, Takashi; Nagahama, Yoshiyuki; Hasegawa, Masakazu; Yamada, Koji; Teranishi, Sakiko; Sato, Haruhiko; Kaneko, Chikara. The chemistry of indoles. CIII. Simple syntheses of serotonin, N-methylserotonin, bufotenine, 5-m

Material Safety Data Sheet (MSDS)

Not Available

General References

Takeda N, Ikeda R, Ohba K, Kondo M: Bufotenine reconsidered as a diagnostic indicator of psychiatric disorders. Neuroreport. 1995 Nov 27;6(17):2378-80. [PubMed:8747157 ]

Enzymes

Enzyme Details

1. Amine oxidase [flavin-containing] A

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21397
Molecular weight:: 59681.27

Enzyme Details

2. Indolethylamine N-methyltransferase

General function:: Involved in methyltransferase activity
Specific function:: Functions as thioether S-methyltransferase and is active with a variety of thioethers and the corresponding selenium and tellurium compounds, including 3-methylthiopropionaldehyde, dimethyl selenide, dimethyl telluride, 2-methylthioethylamine, 2-methylthioethanol, methyl-n-propyl sulfide and diethyl sulfide. Plays an important role in the detoxification of selenium compounds (By similarity). Catalyzes the N-methylation of tryptamine and structurally related compounds.
Gene Name:: INMT
Uniprot ID:: O95050
Molecular weight:: 28833.695

Reactions

S-Adenosylmethionine + Serotonin → S-Adenosylhomocysteine + N-Methylserotonin	details

Showing metabocard for N-Methylserotonin (HMDB0004369)

MOL for HMDB0004369 (N-Methylserotonin)

3D MOL for HMDB0004369 (N-Methylserotonin)

3D SDF for HMDB0004369 (N-Methylserotonin)

3D-SDF for HMDB0004369 (N-Methylserotonin)

PDB for HMDB0004369 (N-Methylserotonin)

3D PDB for HMDB0004369 (N-Methylserotonin)

SMILES for HMDB0004369 (N-Methylserotonin)

INCHI for HMDB0004369 (N-Methylserotonin)

Structure for HMDB0004369 (N-Methylserotonin)

3D Structure for HMDB0004369 (N-Methylserotonin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra

Enzymes

Reactions