NP-MRD: Showing NP-Card for N-Methylserotonin (NP0083365)

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Record Information

Version

2.0

Created at

2022-04-29 04:24:24 UTC

Updated at

2022-04-29 04:24:24 UTC

NP-MRD ID

NP0083365

Secondary Accession Numbers

None

Natural Product 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. N-Methylserotonin is found in Amanita citrina, Bufo bufo, Citrus unshiu , Homo sapiens and Phyllodium pulchellum. N-Methylserotonin was first documented in 1995 (PMID: 8747157). 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 (PMID: 11201232) (PMID: 19649617).

Structure

MOL 3D MOL SDF 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>
NP0083365

> <DATABASE_NAME>
NP-MRD

> <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

View in JSmol

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 Mass

190.2417 Da

Monoisotopic Mass

190.11061 Da

IUPAC Name

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

Traditional Name

N-methylserotonin

CAS Registry Number

Not Available

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

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Amanita citrina	LOTUS Database	35616633
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anser anser	FooDB	FooDB
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Bufo bufo	LOTUS Database	35616633
Capra aegagrus hircus	FooDB	FooDB
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Citrus unshiu	Plant	KNApSAcK
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Gallus gallus	FooDB	FooDB
Homo sapiens	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Phyllodium pulchellum	LOTUS Database	35616633
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

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 )

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
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

External Links

HMDB ID

HMDB0004369

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

Good Scents ID

Not Available

References

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. doi: 10.1097/00001756-199511270-00024. [PubMed:8747157 ]
Somei M, Yamada F, Kurauchi T, Nagahama Y, Hasegawa M, Yamada K, Teranishi S, Sato H, Kaneko C: The chemistry of indoles. CIII. Simple syntheses of serotonin, N-methylserotonin, bufotenine, 5-methoxy-N-methyltryptamine, bufobutanoic acid, N-(indol-3-yl)methyl-5-methoxy-N-methyltryptamine, and lespedamine based on 1-hydroxyindole chemistry. Chem Pharm Bull (Tokyo). 2001 Jan;49(1):87-96. doi: 10.1248/cpb.49.87. [PubMed:11201232 ]
Patkar AA, Rozen S, Mannelli P, Matson W, Pae CU, Krishnan KR, Kaddurah-Daouk R: Alterations in tryptophan and purine metabolism in cocaine addiction: a metabolomic study. Psychopharmacology (Berl). 2009 Oct;206(3):479-89. doi: 10.1007/s00213-009-1625-1. Epub 2009 Aug 1. [PubMed:19649617 ]

Showing NP-Card for N-Methylserotonin (NP0083365)

MOL for NP0083365 (N-Methylserotonin)

3D MOL for NP0083365 (N-Methylserotonin)

3D SDF for NP0083365 (N-Methylserotonin)

3D-SDF for NP0083365 (N-Methylserotonin)

PDB for NP0083365 (N-Methylserotonin)

3D PDB for NP0083365 (N-Methylserotonin)

SMILES for NP0083365 (N-Methylserotonin)

INCHI for NP0083365 (N-Methylserotonin)

Structure for NP0083365 (N-Methylserotonin)

3D Structure for NP0083365 (N-Methylserotonin)