NOMIFENSINE

US Previously Marketed

First approved in 1984

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H18N2
Molecular Weight	238.3275
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1CC(C2=CC=CC=C2)C3=CC=CC(N)=C3C1

InChI

InChIKey=XXPANQJNYNUNES-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C16H18N2
Molecular Weight	238.3275
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/844493 | https://www.ncbi.nlm.nih.gov/pubmed/20742679

Nomifensine was developed by Hoechst AG as a potent inhibitor of noradrenaline, dopamine, and 5-HT uptake displayed antidepressant activity. It was first marketed in the UK in 1977 for the treatment of depression. Between 1977 and 1982 there were reports of hemolytic anemia in association with the drug, and this suspected adverse reaction was included in the 1981 edition of the data Sheet Compendium. FDA published a notice of its determination that Merital capsules were removed from the market for safety reasons.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
norepinephrine uptake 18 Target ID: GO:0051620 Sources: https://www.ncbi.nlm.nih.gov/pubmed/844493	Inhibitor 8504	4.7 nM [Ki]
dopamine uptake 14 Target ID: GO:0090494 Sources: https://www.ncbi.nlm.nih.gov/pubmed/844493	Inhibitor 8504	26.0 nM [Ki]
serotonin uptake 20 Target ID: GO:0051610 Sources: https://www.ncbi.nlm.nih.gov/pubmed/844493	Inhibitor 8504	4.0 µM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Depression 240 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3907935	Primary		Withdrawn	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
53 ng/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/7049645	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		NOMIFENSINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
84 μg/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7082545	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		NOMIFENSINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
196.8 μg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7082545	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		NOMIFENSINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.2 h REVIEW https://pubmed.ncbi.nlm.nih.gov/7049645	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		NOMIFENSINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN
1.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7082545	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		NOMIFENSINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
25% REVIEW https://pubmed.ncbi.nlm.nih.gov/7049645	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:		NOMIFENSINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
150 mg 2 times / day multiple, oral Studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2651559	unhealthy, 18-44 years Health Status: unhealthy Age Group: 18-44 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/2651559	Disc. AE: Skin rash, Fever... AEs leading to discontinuation/dose reduction: Skin rash (severe, 1 patient) Fever (severe, 1 patient) Back pain (severe, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/2651559
100 mg single, intravenous Dose: 100 mg Route: intravenous Route: single Dose: 100 mg Sources: https://pubmed.ncbi.nlm.nih.gov/3956054	healthy, 22-41 years Health Status: healthy Age Group: 22-41 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/3956054	Sources: https://pubmed.ncbi.nlm.nih.gov/3956054

AEs

AE	Significance	Dose	Population
Back pain	severe, 1 patient Disc. AE	150 mg 2 times / day multiple, oral Studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2651559	unhealthy, 18-44 years Health Status: unhealthy Age Group: 18-44 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/2651559
Fever	severe, 1 patient Disc. AE	150 mg 2 times / day multiple, oral Studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2651559	unhealthy, 18-44 years Health Status: unhealthy Age Group: 18-44 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/2651559
Skin rash	severe, 1 patient Disc. AE	150 mg 2 times / day multiple, oral Studied dose Dose: 150 mg, 2 times / day Route: oral Route: multiple Dose: 150 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2651559	unhealthy, 18-44 years Health Status: unhealthy Age Group: 18-44 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/2651559

Sourcing

Vendor/Aggregator	ID	URL
AbMole Bioscience	M2886	http://www.abmole.com/products/nomifensine-maleate.html
Achemtek	0104-021588	http://www.achemtek.com/32795-47-4
AHH Chemical co.,ltd	MT-57174	http://www.ahhchemical.com/product/MT-57174.html
AK Scientific, Inc. (AKSCI)	2594AH	http://www.aksci.com/item_detail.php?cat=2594AH
Ambeed	A428762	https://www.ambeed.com/products/32795-47-4.html
Ambinter	Amb10843762	http://www.ambinter.com/reference/10843762
Aurora Fine Chemicals LLC	A17.880.045	http://online.aurorafinechemicals.com/info?ID=A17.880.045
BioCrick	BCC7226	http://www.biocrick.com/Nomifensine-BCC7226.html
BioSynth	J-018882	https://www.biosynth.com/en/products/all-products/products/J-018882.html
BLD Pharm	BD145381	http://www.bldpharm.com/products/32795-47-4.html
Chem Scene	CS-4709	http://www.chemscene.com/32795-47-4.html
eNovation Chemicals	D671289	https://www.enovationchem.com/ProductDetails.asp?ProductID=D671289
Excenen	EX-A3993	https://www.excenen.com/searchresultlist.php?id=EX-A3993
iChemical	EBD3055579	http://www.ichemical.com/products/32795-47-4.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
Lab Network	LN01306593	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01306593
LGC Standards	LGCFOR3158.00	https://www.lgcstandards.com/US/en/p/LGCFOR3158.00
MedChem Express	HY-B1110A	https://www.medchemexpress.com/Nomifensine-maleate.html
MolPort	MolPort-003-666-476	https://www.molport.com/shop/molecule-link/MolPort-003-666-476
Sigma-Aldrich	N1530_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/n1530?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Smolecule	S537458	http://www.smolecule.com/products/s537458
THE BioTek	bt-277462	https://www.thebiotek.com/product/inhibitors/bt-277462

PubMed

Title	Date	PubMed
Antidepressant-like effect of D(2/3) receptor-, but not D(4) receptor-activation in the rat forced swim test.	2005-07	15688083
Dopamine transporters are involved in the onset of hypoxia-induced dopamine efflux in striatum as revealed by in vivo microdialysis.	2005-06	15863240
Nicotine and epibatidine alter differently nomifensine-elevated dopamine output in the rat dorsal and ventral striatum.	2005-03-28	15792782
Dyskinesias in normal squirrel monkeys induced by nomifensine and levodopa.	2005-03	15721172
Monoamine transporter inhibitors and norepinephrine reduce dopamine-dependent iron toxicity in cells derived from the substantia nigra.	2005-03	15715653
Dopamine transporter function differences between male and female CD-1 mice.	2005-02-28	15722058
D2 autoreceptor inhibition reveals oxygen-glucose deprivation-induced release of dopamine in guinea-pig cochlea.	2005	15837140
Dopamine release evoked by beta scorpion toxin, tityus gamma, in prefrontal cortical slices is mediated by intracellular calcium stores.	2004-12	15672678
Involvement of dopamine receptors in the anti-immobility effects of dopamine re-uptake inhibitors in the forced swimming test.	2004-11-19	15541423
Reduced inhibitory action of a GABAB receptor agonist on [3H]-dopamine release from rat ventral tegmental area in vitro after chronic nicotine administration.	2004-10-20	15494079
Voltammetric study of the control of striatal dopamine release by glutamate.	2004-10	15379902
Methamphetamine neurotoxicity in dopamine nerve endings of the striatum is associated with microglial activation.	2004-10	15163680
Opioid and monoamine systems mediate the discriminative stimulus of tramadol in rats.	2004-09-13	15363988
Inhibitory effect of nitric oxide on dopamine transporters: interneuronal communication without receptors.	2004-09	15186914
Nomifensine amplifies subsecond dopamine signals in the ventral striatum of freely-moving rats.	2004-08	15287895
Prenatal cocaine exposure decreases nigrostriatal dopamine release in vitro: effects of age and sex.	2004-08	15170820
[Dopaminergic regulation of theta activity of septohippocampal neuron in the awake rabbit].	2004-06-04	15174266
[Effects of anxiolytic drugs on rewarding and aversive behaviors induced by intracranial stimulation].	2004-06	15291239
Induction of gp130-related cytokines and activation of JAK2/STAT3 pathway in astrocytes precedes up-regulation of glial fibrillary acidic protein in the 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine model of neurodegeneration: key signaling pathway for astrogliosis in vivo?	2004-05-07	14996842
Methylphenidate restores ventral tegmental area dopamine neuron activity in prenatal ethanol-exposed rats by augmenting dopamine neurotransmission.	2004-05	14724217
Uptake inhibitors but not substrates induce protease resistance in extracellular loop two of the dopamine transporter.	2004-03	14978248
(-)-Deprenyl inhibits tyramine-induced noradrenaline release, but not tyramine-induced dopamine release or potassium-induced noradrenaline release, from rat brain synaptosomes.	2004-03	14726221
Sibutramine induces potential-dependent exocytotic release but not carrier-mediated release of dopamine and 5-hydroxytryptamine.	2004-01-26	14744605
Mechanisms underlying domoic acid-induced dopamine release from striatum: an in vivo microdialysis study.	2003-10	14570393
Enhanced attention in rhesus monkeys as a common factor for the cognitive effects of drugs with abuse potential.	2003-09	12768267
In vitro pharmacological characterization of (+/-)-4-[2-(1-methyl-2-pyrrolidinyl)ethyl]thio]phenol hydrochloride (SIB-1553A), a nicotinic acetylcholine receptor ligand.	2003-08-15	12885429
Dopamine induces autophagic cell death and alpha-synuclein increase in human neuroblastoma SH-SY5Y cells.	2003-08-01	12868068
The effects of systemically administered taurine and N-pivaloyltaurine on striatal extracellular dopamine and taurine in freely moving rats.	2003-08	12898127
Identification of dopamine transporter in bovine pineal gland using [3H]GBR 12935.	2003-08	12823609
Differential effects of amphetamine transport vs. dopamine reverse transport on particulate PKC activity in striatal synaptoneurosomes.	2003-08	12740868
Discriminative stimulus effects of (-)-ephedrine in rats: analysis with catecholamine transporter and receptor ligands.	2003-06-05	12757963
Differences in norepinephrine clearance in cerebellar slices from low-alcohol-sensitive and high-alcohol-sensitive rats.	2003-05	12878270
8-[3H]-hydroxy-2-(di-n-propylamino)tetralin binding sites in blood lymphocytes of rats and the modulation by mitogens and immobilization.	2003-05	12742647
High-frequency stimulation of the subthalamic nucleus enhances striatal dopamine release and metabolism in rats.	2003-05	12694386
Tetrahydrobiopterin precursor sepiapterin provides protection against neurotoxicity of 1-methyl-4-phenylpyridinium in nigral slice cultures.	2003-04	12641743
Functionally distinct dopamine and octopamine transporters in the CNS of the cabbage looper moth.	2003-02	12581206
Mechanism by which brain-derived neurotrophic factor increases dopamine release from the rabbit retina.	2003-02	12556415
Strain-dependent modification of behavior following antidepressant treatment.	2003-02	12551720
A role for presynaptic mechanisms in the actions of nomifensine and haloperidol.	2003	12710989
Aged Fischer 344 rats exhibit altered orolingual motor function: relationships with nigrostriatal neurochemical measures.	2002-12-25	12498959
In vivo evidence for a lack of central effect of ebastine, an antihistaminic agent, in rats: a microdialysis study.	2002-12	12501012
Destruction of serotonergic nerve terminals prevents fluoxetine-induced desensitization of hypothalamic 5-HT(1A) receptors.	2002-12	12457269
Dopamine, but not norepinephrine or serotonin, reuptake inhibition reverses motor deficits in 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-treated primates.	2002-12	12438514
Aged Fischer 344 rats exhibit altered locomotion in the absence of decreased locomotor activity: exacerbation by nomifensine.	2002-11-29	12429381
Kinetic analysis of striatal clearance of exogenous dopamine recorded by chronoamperometry in freely-moving rats.	2002-11-15	12393160
Selective blockade of drug-induced place preference conditioning by ACPC, a functional NDMA-receptor antagonist.	2002-11	12431848
FR143166 attenuates spinal pain transmission through activation of the serotonergic system.	2002-10-11	12359273
In vivo temporal sequence of rat striatal glutamate, aspartate and dopamine efflux during apomorphine, nomifensine, NMDA and PDC in situ administration.	2002-10	12384168
Modification of the striatal dopaminergic neuron system by carbon monoxide exposure in free-moving rats, as determined by in vivo brain microdialysis.	2002-10	12373456
Effects of sibutramine on the central dopaminergic system in rodents.	2001-07	15111248

Patents

Sample Use Guides

In Vivo Use Guide

100 mg at night

Route of Administration: Oral

In Vitro Use Guide

The effect of nomifensine on the uptake of 5-hydroxytryptamine (5-HT) and dopamine (DA) into human platelet-rich plasma has been studied. A significant inhibition of DA uptake was observed at nomifensine 10(-6) M. 5-HT uptake was significantly inhibited only at nomifensine 10(-4) M or more. It was concluded, that the human platelet may be used as a model for studying DA uptake as well as that of 5-HT.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:36:11 GMT 2025` Edited by `admin` on `Mon Mar 31 21:36:11 GMT 2025`
Record UNII	1LGS5JRP31
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NOMIFENSIN

Preferred Name

English

NOMIFENSINE

Official Name

English

1,2,3,4-TETRAHYDRO-2-METHYL-4-PHENYL-8-ISOQUINOLINAMINE

Systematic Name

English

2-METHYL-4-PHENYL-1,2,3,4-TETRAHYDROISOQUINOLIN-8-YLAMINE

Systematic Name

English

NOMIFENSINE [MI]

Common Name

English

NOMIFENSINE [HSDB]

Common Name

English

8-ISOQUINOLINAMINE, 1,2,3,4-TETRAHYDRO-2-METHYL-4-PHENYL-

Systematic Name

English

(±)-NOMIFENSINE

Common Name

English

LINAMIPHEN

Common Name

English

(±)-NOMIFENSIN

Common Name

English

nomifensine [INN]

Common Name

English

Nomifensine [WHO-DD]

Common Name

English

ISOQUINOLINE, 8-AMINO-1,2,3,4-TETRAHYDRO-2-METHYL-4-PHENYL-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C265