Showing Compound 1-Benzyl-1,2,3,4-tetrahydroisoquinoline (FDB023308)

Record Information

Version

1.0

Creation date

2011-09-21 00:27:50 UTC

Update date

2015-07-21 06:57:38 UTC

Primary ID

FDB023308

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

1-Benzyl-1,2,3,4-tetrahydroisoquinoline

Description

1-benzyl-1,2,3,4-tetrahydroisoquinoline (1BnTIQ) as a possible PD-eliciting neurotoxin and evaluated its characteristics relevant to Parkinson disease (PD). 1BnTIQ exist in mammals and is proposed as possible PD-eliciting neurotoxin. PD is believed to be induced by the interaction of genetic predisposition and environmental factors, and a type of neurotoxin is proposed to be one of the environmental factors. 1BnTIQ inhibits [3H] dopamine uptake in HEK293 cells which stably express dopamine transporter. 1BnTIQ also inhibits NADH-ubiquinone oxidoreductase (complex I) in the mitochondrial respiratory chain. 1BnTIQ decreases the dopamine content in the mesencephalon in both dose- and time-dependent manners and it irreversibly reduced the dopamine content. Furthermore, it causes morphological changes in tyrosine hydroxylase-positive cells in the mesencephalon and reduced the number of cells. (PMID 12440154) [HMDB]

CAS Number

19716-56-4

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(R,S)-Tetrahydrobenzylisoquinoline	ChEBI
(r,s)-tetrahydrobenzylisoquinoline	hmdb
(RS)-1-Benzyl-1,2,3,4-tetrahydroisoquinoline	Kegg
1,2,3,4-Tetrahydro-1-(phenylmethyl)isoquinoline	ChEBI
1,2,3,4-tetrahydro-1-(Phenylmethyl)isoquinoline hydrochloride	MeSH, HMDB
1,2,3,4-tetrahydro-1-(Phenylmethyl)isoquinoline, (+-)-isomer	MeSH, HMDB
1,2,3,4-tetrahydro-1-(Phenylmethyl)isoquinoline, (R)-isomer	MeSH, HMDB
1,2,3,4-tetrahydro-1-(Phenylmethyl)isoquinoline, (S)-isomer	MeSH, HMDB
1-Benzyl-1,2,3,4-tetrahydroisoquinoline	MeSH
1BnTIQ	ChEBI

Showing 1 to 10 of 11 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.0035 g/L	ALOGPS
logP	3.48	ALOGPS
logP	3.64	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	12.03 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	71.65 m³·mol⁻¹	ChemAxon
Polarizability	26.2 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

Chemical Formula

C16H17N

IUPAC name

1-benzyl-1,2,3,4-tetrahydroisoquinoline

InChI Identifier

InChI=1S/C16H17N/c1-2-6-13(7-3-1)12-16-15-9-5-4-8-14(15)10-11-17-16/h1-9,16-17H,10-12H2

InChI Key

YRYCIFUZSUMAAY-UHFFFAOYSA-N

Isomeric SMILES

C(C1NCCC2=CC=CC=C12)C1=CC=CC=C1

Average Molecular Weight

223.3129

Monoisotopic Molecular Weight

223.136099549

Classification

Description

Belongs to the class of organic compounds known as benzylisoquinolines. These are organic compounds containing an isoquinoline to which a benzyl group is attached.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoquinolines and derivatives

Sub Class

Benzylisoquinolines

Direct Parent

Benzylisoquinolines

Alternative Parents

Substituents

Benzylisoquinoline
Tetrahydroisoquinoline
Aralkylamine
Benzenoid
Monocyclic benzene moiety
Azacycle
Secondary amine
Secondary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzyltetrahydroisoquinoline (CHEBI:16804 )

Ontology

Disposition

Biological location:

Biofluid and excreta:

Cerebrospinal fluid

Subcellular:

Source:

Endogenous

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	1-Benzyl-1,2,3,4-tetrahydroisoquinoline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-001i-2900000000-69767d6f6a91a5c24bd1	Spectrum
Predicted GC-MS	1-Benzyl-1,2,3,4-tetrahydroisoquinoline, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0090000000-75679a6f444b9bd42db4	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05gl-3890000000-5df7dde54dbe0fe2b4fa	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9700000000-3f687e462c9cd0cc1ff2	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-672b95459dab89c79e3c	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0090000000-87a0dda1779b4676ba7c	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0059-1910000000-d2ecf13f470a7ba9cb0e	2017-09-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0090000000-279452a29859034561fa	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0090000000-939f38e3140d9ca30df6	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-005c-2900000000-ed789626d72de391b664	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0090000000-0e93eae718d771100a69	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05fr-2960000000-a0da7d0090f88d305999	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4m-4900000000-148ae7c1169e2d0c08f0	2021-09-23	View Spectrum

NMR

Not Available

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

16804

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB04087

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

Not Available

KNApSAcK ID

Not Available

HET ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Not Available

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Anatidae	Expected but not quantified	Not Available	HMDB
Beefalo	Expected but not quantified	Not Available	HMDB
Bison	Expected but not quantified	Not Available	HMDB
Buffalo	Expected but not quantified	Not Available	HMDB
Cattle (Beef, Veal)	Expected but not quantified	Not Available	HMDB
Chicken	Expected but not quantified	Not Available	HMDB
Columbidae (Dove, Pigeon)	Expected but not quantified	Not Available	HMDB
Deer	Expected but not quantified	Not Available	HMDB
Domestic goat	Expected but not quantified	Not Available	HMDB
Domestic pig	Expected but not quantified	Not Available	HMDB