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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-08-13 17:42:43 UTC
Update Date2020-02-26 21:25:07 UTC
HMDB IDHMDB0004369
Secondary Accession Numbers
  • HMDB04369
Metabolite Identification
Common NameN-Methylserotonin
DescriptionN-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
Data?1582752307
Synonyms
ValueSource
N-Methylserotonin oxalate saltHMDB
3-(2-(Methylamino)ethyl)-1H-indol-5-olHMDB
3-[2-(Methylamino)ethyl]-1H-indol-5-olHMDB
Lopac-m-1514HMDB
Chemical FormulaC11H14N2O
Average Molecular Weight190.2417
Monoisotopic Molecular Weight190.11061308
IUPAC Name3-[2-(methylamino)ethyl]-1H-indol-5-ol
Traditional NameN-methylserotonin
CAS Registry Number1134-01-6
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 KeyASUSBMNYRHGZIG-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassTryptamines and derivatives
Direct ParentSerotonins
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 FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Process

Naturally occurring process

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.75 g/LALOGPS
logP1.55ALOGPS
logP0.69ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)9.45ChemAxon
pKa (Strongest Basic)10.44ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area48.05 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity57.13 m³·mol⁻¹ChemAxon
Polarizability21.4 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+142.86431661259
DarkChem[M-H]-141.67331661259
DeepCCS[M+H]+142.79630932474
DeepCCS[M-H]-138.96830932474
DeepCCS[M-2H]-176.39630932474
DeepCCS[M+Na]+151.93530932474
AllCCS[M+H]+142.432859911
AllCCS[M+H-H2O]+138.232859911
AllCCS[M+NH4]+146.432859911
AllCCS[M+Na]+147.632859911
AllCCS[M-H]-145.632859911
AllCCS[M+Na-2H]-146.032859911
AllCCS[M+HCOO]-146.532859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
N-MethylserotoninCNCCC1=CNC2=C1C=C(O)C=C23161.4Standard polar33892256
N-MethylserotoninCNCCC1=CNC2=C1C=C(O)C=C22049.5Standard non polar33892256
N-MethylserotoninCNCCC1=CNC2=C1C=C(O)C=C22133.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
N-Methylserotonin,1TMS,isomer #1CNCCC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C121986.2Semi standard non polar33892256
N-Methylserotonin,1TMS,isomer #2CN(CCC1=C[NH]C2=CC=C(O)C=C12)[Si](C)(C)C2215.7Semi standard non polar33892256
N-Methylserotonin,1TMS,isomer #3CNCCC1=CN([Si](C)(C)C)C2=CC=C(O)C=C122056.9Semi standard non polar33892256
N-Methylserotonin,2TMS,isomer #1CN(CCC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12)[Si](C)(C)C2220.1Semi standard non polar33892256
N-Methylserotonin,2TMS,isomer #1CN(CCC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12)[Si](C)(C)C2285.8Standard non polar33892256
N-Methylserotonin,2TMS,isomer #1CN(CCC1=C[NH]C2=CC=C(O[Si](C)(C)C)C=C12)[Si](C)(C)C2362.3Standard polar33892256
N-Methylserotonin,2TMS,isomer #2CNCCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C122041.7Semi standard non polar33892256
N-Methylserotonin,2TMS,isomer #2CNCCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C122139.9Standard non polar33892256
N-Methylserotonin,2TMS,isomer #2CNCCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C122265.6Standard polar33892256
N-Methylserotonin,2TMS,isomer #3CN(CCC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)[Si](C)(C)C2296.0Semi standard non polar33892256
N-Methylserotonin,2TMS,isomer #3CN(CCC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)[Si](C)(C)C2368.1Standard non polar33892256
N-Methylserotonin,2TMS,isomer #3CN(CCC1=CN([Si](C)(C)C)C2=CC=C(O)C=C12)[Si](C)(C)C2391.5Standard polar33892256
N-Methylserotonin,3TMS,isomer #1CN(CCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)[Si](C)(C)C2293.6Semi standard non polar33892256
N-Methylserotonin,3TMS,isomer #1CN(CCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)[Si](C)(C)C2305.9Standard non polar33892256
N-Methylserotonin,3TMS,isomer #1CN(CCC1=CN([Si](C)(C)C)C2=CC=C(O[Si](C)(C)C)C=C12)[Si](C)(C)C2246.5Standard polar33892256
N-Methylserotonin,1TBDMS,isomer #1CNCCC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C122252.0Semi standard non polar33892256
N-Methylserotonin,1TBDMS,isomer #2CN(CCC1=C[NH]C2=CC=C(O)C=C12)[Si](C)(C)C(C)(C)C2462.8Semi standard non polar33892256
N-Methylserotonin,1TBDMS,isomer #3CNCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C122305.2Semi standard non polar33892256
N-Methylserotonin,2TBDMS,isomer #1CN(CCC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)[Si](C)(C)C(C)(C)C2710.0Semi standard non polar33892256
N-Methylserotonin,2TBDMS,isomer #1CN(CCC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)[Si](C)(C)C(C)(C)C2733.2Standard non polar33892256
N-Methylserotonin,2TBDMS,isomer #1CN(CCC1=C[NH]C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C12)[Si](C)(C)C(C)(C)C2585.5Standard polar33892256
N-Methylserotonin,2TBDMS,isomer #2CNCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C122504.2Semi standard non polar33892256
N-Methylserotonin,2TBDMS,isomer #2CNCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C122583.3Standard non polar33892256
N-Methylserotonin,2TBDMS,isomer #2CNCCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O[Si](C)(C)C(C)(C)C)C=C122468.6Standard polar33892256
N-Methylserotonin,2TBDMS,isomer #3CN(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)[Si](C)(C)C(C)(C)C2723.1Semi standard non polar33892256
N-Methylserotonin,2TBDMS,isomer #3CN(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)[Si](C)(C)C(C)(C)C2792.8Standard non polar33892256
N-Methylserotonin,2TBDMS,isomer #3CN(CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(O)C=C12)[Si](C)(C)C(C)(C)C2572.4Standard polar33892256
N-Methylserotonin,3TBDMS,isomer #1CN(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)C2953.0Semi standard non polar33892256
N-Methylserotonin,3TBDMS,isomer #1CN(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)C2930.1Standard non polar33892256
N-Methylserotonin,3TBDMS,isomer #1CN(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)C2572.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - N-Methylserotonin GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-514cf662a4e6c5a603df2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Methylserotonin GC-MS (1 TMS) - 70eV, Positivesplash10-0006-9120000000-4c9438c3246e1f92d1f52017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - N-Methylserotonin 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 - N-Methylserotonin 10V, Negative-QTOFsplash10-000i-0900000000-b4a2e8f1bf6e3e7826902015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylserotonin 20V, Negative-QTOFsplash10-000i-0900000000-970029b3b4e6dd32e53a2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylserotonin 40V, Negative-QTOFsplash10-001i-2900000000-9851a5693e2c284d3b9d2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylserotonin 10V, Negative-QTOFsplash10-000i-0900000000-737a601f9d97628ca5082021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylserotonin 20V, Negative-QTOFsplash10-0019-0900000000-58467315e6d4795f24882021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylserotonin 40V, Negative-QTOFsplash10-001i-2900000000-cdd5d680769ece6297e42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylserotonin 10V, Positive-QTOFsplash10-01ox-0900000000-646686588892f9e597f52015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylserotonin 20V, Positive-QTOFsplash10-03dl-1900000000-a768b9399c8fcac6cd0e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylserotonin 40V, Positive-QTOFsplash10-01q9-2900000000-543fe5365e1fa682b60e2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylserotonin 10V, Positive-QTOFsplash10-01ox-0900000000-068fac34efa1b5ba779c2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylserotonin 20V, Positive-QTOFsplash10-03di-0900000000-46a702a381d3892e40b42021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - N-Methylserotonin 40V, Positive-QTOFsplash10-0f8c-2900000000-d17d6394f323b90f889c2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
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 IDFDB017273
KNApSAcK IDNot Available
Chemspider ID132989
KEGG Compound IDC06212
BioCyc IDNot Available
BiGG ID47668
Wikipedia LinkN-Methylserotonin
METLIN ID7056
PubChem Compound150885
PDB IDNot Available
ChEBI ID48294
Food Biomarker OntologyNot Available
VMH IDNMTHSRTN
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceSomei, 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
  1. 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

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
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-Methylserotonindetails