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24526-64-5 molecular structure
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2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinolin-8-amine

ChemBase ID: 4365
Molecular Formular: C16H18N2
Molecular Mass: 238.32752
Monoisotopic Mass: 238.14699859
SMILES and InChIs

SMILES:
N1(CC(c2c(C1)c(N)ccc2)c1ccccc1)C
Canonical SMILES:
CN1CC(c2ccccc2)c2c(C1)c(N)ccc2
InChI:
InChI=1S/C16H18N2/c1-18-10-14(12-6-3-2-4-7-12)13-8-5-9-16(17)15(13)11-18/h2-9,14H,10-11,17H2,1H3
InChIKey:
XXPANQJNYNUNES-UHFFFAOYSA-N

Cite this record

CBID:4365 http://www.chembase.cn/molecule-4365.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinolin-8-amine
IUPAC Traditional name
nomifensine
Brand Name
Linamiphen
Nomifenison
Merital
Synonyms
(+)-nomifensine
(+)-nomiphensine
(+-)-nomifensin
(+-)-nomifensine
(R)-1,2,3,4-Tetrahydro-2-methyl-4-phenyl-8-isoquinolinamine
2-Methyl-4-phenyl-1,2,3,4-tetrahydro-8-isoquinolinamine
8-Amino-1,2,3,4-tetrahydro-2-methyl-4-phenylisochinolin
8-Amino-1,2,3,4-tetrahydro-2-methyl-4-phenylisoquinoline
8-Amino-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline
Nomifensina [inn-spanish]
Nomifensine hydrogen maleate
Nomifensine maleate
Nomifensinum [inn-latin]
Nomifensin
Nomifensine
2-Methyl-4-phenyl-1,2,3,4-tetrahydroisoquinolin-8-amine
CAS Number
24526-64-5
PubChem SID
46505804
160967797
PubChem CID
4528

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
Bide Pharmatech
BD145380 Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) -0.51397175  LogD (pH = 7.4) 1.1298963 
Log P 2.624382  Molar Refractivity 77.1773 cm3
Polarizability 29.208132 Å3 Polar Surface Area 29.26 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 2.94  LOG S -2.87 
Solubility (Water) 3.18e-01 g/l 

PROPERTIES

PROPERTIES

Product Information Bioassay(PubChem)
Purity
95+% expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB04821 external link
Item Information
Drug Groups withdrawn
Description Nomifensine, formerly marketed as Merital capsules, was associated with an increased incidence of hemolytic anemia. The approved application holder removed Merital capsules from the market on January 23, 1986. FDA published a notice of its determination that Merital capsules were removed from the market for safety reasons (see the Federal Register of June 17, 1986 (51 FR 21981)). Approval of the NDA for Merital capsules was withdrawn on March 20, 1992 (see the Federal Register of March 20, 1992 (57 FR 9729)). Also withdrawn from the Canadian and UK markets.
Pharmacology Nomifensine is a dopamine reuptake inhibitor test-marketed in the United States by Hoechst AG (now Novartis) that increases the amount of synaptic dopamine available to receptors by blocking dopamine's re-uptake transporter. Nomifensine is now mainly used in scientific research, particularly in studies involving dopamine release in response to addiction.
Toxicity A likely cause of nomifensine toxicity is the aromatic amine group, as compounds containing this chemical substructure are notorious for producing toxic metabolites.
Affected Organisms
Humans and other mammals
External Links
Wikipedia

REFERENCES

REFERENCES

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PATENTS

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