ChemFOnt: Showing chemical card for 2(N)-Methyl-norsalsolinol (CFc000000925)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:45:27 UTC

Chemfont ID

CFc000000925

Molecule Identification

Common Name

2(N)-Methyl-norsalsolinol

Definition

2(N)-methyl-norsalsolinol (NMNorsal) is a dihydroxylated tetrahydroisoquinoline derivative 2(N)-analogue of salsolinol, identified as a putative endogenous neurotoxin in patients with Parkinson's disease. A prominent blood-brain barrier (BBB) is described to exist for salsolinol, but penetration of NMNorsal occurs through the BBB into the caudate nucleus of the rat brain. There was no alteration in extracellular dopamine or 3,4-dihydroxyphenylacetic acid levels. (PMID 11924888 ). 2(N)-methyl-norsalsolinol was identified in L-DOPA-treated patients with Parkinson's disease and proposed to be responsible for behavioral changes. Atypical heterocyclic L-DOPA/dopamine metabolite NMNorsal is able to modify long-term regulation of serotonin and opioid receptor expression in striatum. Since the occurrence of hallucinosis or psychosis following L-DOPA treatment is related to the serotonergic system, these results probably reflect a link between NMNorsal and L-DOPA side effects in Parkinson's disease. (PMID 14607311 ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1,2,3,4-tetrahydro-2-Methyl-6,7-isoquinolinediol	HMDB
2-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline	HMDB, MeSH
2-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrobromide	MeSH, HMDB
NMNSAL	MeSH, HMDB
2-MDTIQ	MeSH, HMDB
2-Methyl-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride	MeSH, HMDB
N-Methylnorsalsolinol	MeSH, HMDB

Chemical Formula

C₁₀H₁₃NO₂

Average Molecular Weight

179.2157

Monoisotopic Molecular Weight

179.094628665

IUPAC Name

2-methyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol

Traditional Name

2(N)-methyl-norsalsolinol

CAS Registry Number

63937-92-8

SMILES

CN1CCC2=CC(O)=C(O)C=C2C1

InChI Identifier

InChI=1S/C10H13NO2/c1-11-3-2-7-4-9(12)10(13)5-8(7)6-11/h4-5,12-13H,2-3,6H2,1H3

InChI Key

WETXYFNVBDLWIW-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydroisoquinolines

Sub Class

Not Available

Direct Parent

Tetrahydroisoquinolines

Alternative Parents

Substituents

Tetrahydroisoquinoline
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Cerebrospinal Fluid (CSF) (PMID: 7595645)
Cerebrospinal fluid (HMDB: HMDB0001189)

Source

Endogenous

Endogenous (HMDB: HMDB0001189)

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)

Process

Not Available

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	37.1 g/L	ALOGPS
logP	0.59	ALOGPS
logP	1.35	ChemAxon
logS	-0.68	ALOGPS
pKa (Strongest Acidic)	9.43	ChemAxon
pKa (Strongest Basic)	7.47	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	43.7 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	51.87 m³·mol⁻¹	ChemAxon
Polarizability	19.56 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

HMDB0001189

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022477

KNApSAcK ID

Not Available

Chemspider ID

34632

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

37764

PDB ID

Not Available

ChEBI ID

767276

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for 2(N)-Methyl-norsalsolinol (CFc000000925)

MOL for CFc000000925 (2(N)-Methyl-norsalsolinol)

3D MOL for CFc000000925 (2(N)-Methyl-norsalsolinol)

3D SDF for CFc000000925 (2(N)-Methyl-norsalsolinol)

3D-SDF for CFc000000925 (2(N)-Methyl-norsalsolinol)

PDB for CFc000000925 (2(N)-Methyl-norsalsolinol)

3D PDB for CFc000000925 (2(N)-Methyl-norsalsolinol)

SMILES for CFc000000925 (2(N)-Methyl-norsalsolinol)

INCHI for CFc000000925 (2(N)-Methyl-norsalsolinol)

Structure for CFc000000925 (2(N)-Methyl-norsalsolinol)

3D Structure for CFc000000925 (2(N)-Methyl-norsalsolinol)