Name: NOMIFENSINE MALEATE
SKU: 24526-64-5

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Basic Information

Molecular Structure:
CAS No.:	24526-64-5
Name:	NOMIFENSINE MALEATE
Article Data:	8

Formula:	C16H18 N2
Molecular Weight:	238.332
Synonyms:	Isoquinoline,8-amino-1,2,3,4-tetrahydro-2-methyl-4-phenyl- (8CI); (?à)-Nomifensin; (?à)-Nomifensine; 2-Methyl-4-phenyl-1,2,3,4-tetrahydroisoquinolin-8-ylamine;Linamiphen; Nomifensin; Nomifensine
Density:	1.114g/cm³
Melting Point:	179-181°
Boiling Point:	378.4°Cat760mmHg
Flash Point:	164°C
Hazard Symbols:
Risk Codes:	22-36/37/38
Safety:	Poison by ingestion and intravenous routes. Human systemic effects by ingestion: diffuse hepatitis, hemorrhage and decrease in the number of blood platelets (thrombocytopenia). When heated to decomposition it emits toxic fumes of NO_x. See also NOMIFENSINE MALEATE.
PSA:	29.26000
LogP:	3.36520

Synthetic route

: 96-09-3
styrene oxide

: 56222-08-3
(2-nitrobenzyl)methylamine

: 24526-64-5
nomifensine

Conditions

Conditions	Yield
Yield given. Multistep reaction;

: 65514-97-8
N-(2-Aminobenzyl)-2-(methylamino)-1-phenyl-1-ethanol

: 24526-64-5
nomifensine

Conditions

Conditions	Yield
With hydrogenchloride; sulfuric acid; zinc 1) EtOH, 0 - 5 deg C, 2) CH2Cl2, r.t., 10 - 12 h; Yield given. Multistep reaction;
With sulfuric acid In dichloromethane at 6 - 8℃; for 0.5h;
With sulfuric acid In dichloromethane at 0 - 20℃; for 0.333333h;

: 56222-08-3
(2-nitrobenzyl)methylamine

: 24526-64-5
nomifensine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 93 percent / triethylamine / diethyl ether / 4 h / 18 - 25 °C 2: 88 percent / NaBH4 / methanol; H2O / 4 h / Ambient temperature 3: 87 percent / H2 / Raney nickel / ethanol / 12 h / 760 Torr 4: conc. H2SO4 / CH2Cl2 / 0.5 h / 6 - 8 °C View Scheme

: 102436-67-9
2-acetophenone

: 24526-64-5
nomifensine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 88 percent / NaBH4 / methanol; H2O / 4 h / Ambient temperature 2: 87 percent / H2 / Raney nickel / ethanol / 12 h / 760 Torr 3: conc. H2SO4 / CH2Cl2 / 0.5 h / 6 - 8 °C View Scheme

: 70-11-1
α-bromoacetophenone

KOH: KOH

: 24526-64-5
nomifensine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 93 percent / triethylamine / diethyl ether / 4 h / 18 - 25 °C 2: 88 percent / NaBH4 / methanol; H2O / 4 h / Ambient temperature 3: 87 percent / H2 / Raney nickel / ethanol / 12 h / 760 Torr 4: conc. H2SO4 / CH2Cl2 / 0.5 h / 6 - 8 °C View Scheme

: 85660-33-9
N-(2-Nitrobenzyl)-2-(methylamino)-1-phenyl-1-ethanol

: 24526-64-5
nomifensine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 87 percent / H2 / Raney nickel / ethanol / 12 h / 760 Torr 2: conc. H2SO4 / CH2Cl2 / 0.5 h / 6 - 8 °C View Scheme

: 119810-30-9
2-[(2-Amino-benzyl)-methyl-amino]-1-phenyl-ethanone

: 24526-64-5
nomifensine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: NaBH4 / 3 h / Ambient temperature 2: 1) zinc, conc. HCl, 2) 98percent H2SO4 / 1) EtOH, 0 - 5 deg C, 2) CH2Cl2, r.t., 10 - 12 h View Scheme
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / ethanol / 1.5 h / 0 - 20 °C 2: sulfuric acid / dichloromethane / 0.33 h / 0 - 20 °C View Scheme

: 532-27-4
1-chloroacetophenone

: 24526-64-5
nomifensine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: methanol / Ambient temperature 2: NaBH4 / 3 h / Ambient temperature 3: 1) zinc, conc. HCl, 2) 98percent H2SO4 / 1) EtOH, 0 - 5 deg C, 2) CH2Cl2, r.t., 10 - 12 h View Scheme

: 1904-69-4
2-amino-N-methylbenzylamine

: 24526-64-5
nomifensine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: methanol / Ambient temperature 2: NaBH4 / 3 h / Ambient temperature 3: 1) zinc, conc. HCl, 2) 98percent H2SO4 / 1) EtOH, 0 - 5 deg C, 2) CH2Cl2, r.t., 10 - 12 h View Scheme
Multi-step reaction with 3 steps 1: methanol / 0.5 h / Ambient temperature 2: NaBH4 / 3 h / Ambient temperature 3: 1) zinc, conc. HCl, 2) 98percent H2SO4 / 1) EtOH, 0 - 5 deg C, 2) CH2Cl2, r.t., 10 - 12 h View Scheme
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 18 h / 20 °C 2: sodium tetrahydroborate / ethanol / 1.5 h / 0 - 20 °C 3: sulfuric acid / dichloromethane / 0.33 h / 0 - 20 °C View Scheme

: 70-11-1
α-bromoacetophenone

: 24526-64-5
nomifensine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: methanol / 0.5 h / Ambient temperature 2: NaBH4 / 3 h / Ambient temperature 3: 1) zinc, conc. HCl, 2) 98percent H2SO4 / 1) EtOH, 0 - 5 deg C, 2) CH2Cl2, r.t., 10 - 12 h View Scheme

Raw Materials

1904-69-4

552-89-6

529-23-7

532-27-4

70-11-1

Downstream Products

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Chemistry

IUPAC Name: 2-Methyl-4-phenyl-3,4-dihydro-1H-isoquinolin-8-amine
Synonyms of Nomifensine (CAS NO.24526-64-5) : 1,2,3,4-Tetrahydro-2-methyl-4-phenyl-8-isoquinolinamine ; 2-Methyl-4-phenyl-1,2,3,4-tetrahydroisoquinolin-8-amine ; 8-Amino-1,2,3,4-tetrahydro-2-methyl-4-phenylisoquinoline ; 8-Isoquinolinamine, 1,2,3,4-tetrahydro-2-methyl-4-phenyl-
CAS NO:24526-64-5
Molecular Formula :C₁₆H₁₈N₂
Molecular Weight:238.32752
Molecular Structure:
Index of Refraction: 1.622
Surface Tension: 46.6 dyne/cm
Density: 1.114 g/cm³
Flash Point: 164 °C
Enthalpy of Vaporization: 62.63 kJ/mol
Boiling Point: 378.4 °C at 760 mmHg
Vapour Pressure: 6.28E-06 mmHg at 25°C

History

Merital was investigated for use as an antidepressant in the 1970s, and was found to be a useful antidepressant at doses of 50-225mg per day, both motivating and anxiolytic. There were relatively few adverse effects (mainly dry mouth, headache, nausea), the drug was not sedating, did not interact significantly with alcohol and lacked anticholinergic effects. No withdrawal symptoms were seen after 6 months treatment. The drug was however considered not suitable for agitated patients as it presumably made agitation worse.
Later studies in the 1980s concluded that there was potential for dependence and abuse of nomifensine, typically in patients with a history of stimulant addiction, or when the drug was used in very high doses (400-600mg per day). Nomifensine is now only rarely used as an antidepressant due to concerns about causing haemolytic anaemia, and problems with overstimulation and hyperthermia in overdose. It has been investigated for use in treating ADHD and animal models of Parkinson's disease with some success. However, it has not proved of benefit to human patients suffering from advanced Parkinsonism.
Nomifensine was withdrawn from mainstream medical use for a variety of reasons, abuse potential being a concern, but also problems with kidney and liver toxicity and haemolytic anaemia were cited, and some deaths were linked to the use of this compound although the mechanism remains unclear. A likely cause of nomifensine toxicity is the anilino group, as compounds containing this chemical substructure are notorious for producing toxic metabolites.

Uses

Nomifensine (CAS NO.24526-64-5) is a norepinephrine-dopamine reuptake inhibitor test-marketed in the United States by Hoechst AG (now Sanofi-Aventis) that increases the amount of synaptic dopamine available to receptors by blocking dopamine's re-uptake transporter. This is a mechanism of action shared by some recreational drugs like cocaine (see DRI).
Nomifensine is now mainly used in scientific research, particularly in studies involving dopamine release in response to addiction. This is because typically different areas of the brain have different amounts of dopamine transporter, but when Nomifensine is administered, a sufficient basal dopamine level is reached to allow comparison of dopamine release from drugs of abuse in different areas of the brain without the results being skewed by re-uptake speed variation.

Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
guinea pig	LD50	intravenous	264mg/kg (264mg/kg)	LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. Vol. 18, Pg. 1, 1979.
mammal (species unspecified)	LD50	oral	300mg/kg (300mg/kg)		German Offenlegungsschrift Patent Document. Vol. #2901868,
mouse	LD50	intraperitoneal	128mg/kg (128mg/kg)		Journal de Pharmacologie. Vol. 17, Pg. 37, 1986.
mouse	LD50	oral	260mg/kg (260mg/kg)	BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BEHAVIORAL: AGGRESSION	Arzneimittel-Forschung. Drug Research. Vol. 32, Pg. 873, 1982.
mouse	LD50	subcutaneous	269mg/kg (269mg/kg)		United States Patent Document. Vol. #4537895,
rat	LD50	oral	267mg/kg (267mg/kg)		Journal of International Medical Research. Vol. 13, Pg. 77, 1985.
women	TDLo	oral	500ug/kg (0.5mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Human Toxicology. Vol. 6, Pg. 247, 1987.
women	TDLo	oral	7mg/kg/7D-I (7mg/kg)	BLOOD: HEMORRHAGE BLOOD: THROMBOCYTOPENIA	British Medical Journal. Vol. 288, Pg. 830, 1984.

Safety Profile

Poison by ingestion and intravenous routes. Human systemic effects by ingestion: diffuse hepatitis, hemorrhage and decrease in the number of blood platelets (thrombocytopenia). When heated to decomposition it emits toxic fumes of NO_x. See also NOMIFENSINE MALEATE.
Hazard Codes Harmful Xn
Risk Statements 22-36/37/38
R22: Nomifensine (CAS NO.24526-64-5) is harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements 26-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S36:Wear suitable protective clothing.
RIDADR 3249
WGK Germany 3
RTECS NX4912800
HazardClass 6.1(b)
PackingGroup III