ContaminantDB: Nantenine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (37)XML

Record Information

Version

1.0

Creation Date

2014-08-29 05:09:22 UTC

Update Date

2026-04-06 02:20:27 UTC

Accession Number

CHEM003063

Identification

Common Name

Nantenine

Class

Small Molecule

Description

Nantenine is an alkaloid found in the plant Nandina domestica as well as some Corydalis species. It is an antagonist at both the alpha-1 adrenergic receptor and the 5-HT2A serotonin receptor, and blocks both the behavioural and physiological effects of MDMA in animals.

Contaminant Sources

T3DB toxins

Contaminant Type

Amine
Ether
Natural Compound
Organic Compound
Plant Toxin

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
O-Methyl-domesticine	MeSH
O-Methyldomesticine	MeSH
Nantenine, (+-)-isomer	MeSH

Chemical Formula

C₂₀H₂₁NO₄

Average Molecular Mass

339.385 g/mol

Monoisotopic Mass

339.147 g/mol

CAS Registry Number

2565-01-7

IUPAC Name

(12S)-18,19-dimethoxy-13-methyl-5,7-dioxa-13-azapentacyclo[10.7.1.0²,¹⁰.0⁴,⁸.0¹⁶,²⁰]icosa-1(20),2,4(8),9,16,18-hexaene

Traditional Name

nantenine

SMILES

[H][C@]12CC3=CC4=C(OCO4)C=C3C3=C1C(CCN2C)=CC(OC)=C3OC

InChI Identifier

InChI=1S/C20H21NO4/c1-21-5-4-11-7-17(22-2)20(23-3)19-13-9-16-15(24-10-25-16)8-12(13)6-14(21)18(11)19/h7-9,14H,4-6,10H2,1-3H3/t14-/m0/s1

InChI Key

WSVWKHTVFGTTKJ-AWEZNQCLSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as aporphines. These are quinoline alkaloids containing the dibenzo[de,g]quinoline ring system or a dehydrogenated derivative thereof.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Aporphines

Sub Class

Not Available

Direct Parent

Aporphines

Alternative Parents

Substituents

Aporphine
Benzoquinoline
Phenanthrene
Naphthalene
Quinoline
Tetrahydroisoquinoline
Benzodioxole
Anisole
Aralkylamine
Alkyl aryl ether
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Organoheterocyclic compound
Azacycle
Oxacycle
Acetal
Ether
Hydrocarbon derivative
Organic oxygen compound
Organopnictogen compound
Organic nitrogen compound
Organonitrogen compound
Amine
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

isoquinoline alkaloid (CHEBI:68992 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB Link	KEGG Link
Antipsychotics	Not Available	Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.079 g/L	ALOGPS
logP	2.77	ALOGPS
logP	3.01	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	7.07	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.16 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.72 m³·mol⁻¹	ChemAxon
Polarizability	36.94 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0009000000-aedb803159bad3817262	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0006-0029000000-b604c56c615e2e1db5b6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01rx-0090000000-d549680894993ac8ef19	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0009000000-232c9ad6c05b122d2302	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-0019000000-220141e4b2288b8735ea	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-1093000000-7f32a139175b35e9cbcc	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Nantenine is an antagonist at both the α1 adrenergic receptor and the 5-HT2A serotonin receptor, and blocks both the behavioural and physiological effects of MDMA in animals (Wikipedia). Nantenine is reported to have 5-HT2A antagonist properties (1).

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Nantenine is an alkaloid found in the plant Nandina domestica as well as some Corydalis species.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

C00025953 C00027150

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Nantenine

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

197001

Kegg Compound ID

C19985

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Nantenine (CHEM003063)

Structure for CHEM003063: Nantenine