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Nortriptyline
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Name

Nortriptyline

 EINECS 200-788-8
CAS No. 72-69-5 Density 1.084 g/cm3
PSA 12.03000 LogP 4.21730
Solubility N/A Melting Point 58 °C
Formula C19H21N Boiling Point 403.4 °C at 760 mmHg
Molecular Weight 263.382 Flash Point 194.9 °C
Transport Information N/A Appearance N/A
Safety Risk Codes N/A
Molecular Structure Molecular Structure of 72-69-5 (NORTRIPTYLINE) Hazard Symbols N/A
Synonyms

5H-Dibenzo[a,d]cycloheptene-D5,g-propylamine, 10,11-dihydro-N-methyl- (8CI);10,11-Dihydro-N-methyl-5H-dibenzo[a,d]cycloheptane-Dgpropylamine;3-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methylpropylamine;5-[3-(Methylamino)propylidene]dibenzo[a,e]cyclohepta[1,5]diene;Ateben;Avantyl;Aventyl;Demethylamitriptyline;Desitriptilina;Lumbeck;NCI 169453;Nortriptyline;Sesaval;

Article Data 34

Nortriptyline Synthetic route

549-18-8

amitriptyline hydrochloride

A

72-69-5

3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

B

1156-99-6

10-Hydroxynortriptyline

C

64520-05-4

(Z)-10-Hydroxyamitriptyline

Conditions
ConditionsYield
With glucose dehydrogenase; D-glucose; cytochrome P450BM3 F87A/H171L/Q307H/N319Y mutant; oxygen; β-nicotinamide adenine dinucleotide phosphate sodium salt In ethanol at 25℃; for 2h; pH=8.5; Enzymatic reaction;A 69%
B n/a
C n/a

N-methyl-4-(2-phenethylphenyl)but-3-yn-1-amine

72-69-5

3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In dichloromethane at 0℃; for 0.166667h; Friedel-Crafts Alkylation; regioselective reaction;68%
16234-88-1

5-<3-(N-Carbethoxy-N-methyl-amino)-propyliden>-10,11-dihydro-dibenzocyclohepten

72-69-5

3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

Conditions
ConditionsYield
With potassium hydroxide In butan-1-ol at 120 - 125℃;
16235-12-4

5-<3-(N-Methyl-p-toluolsulfonamido)-propyliden>-10,11-dihydro-dibenzocyclohepten

72-69-5

3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

Conditions
ConditionsYield
With hydrogen bromide; acetic acid; phenol
16234-89-2

5-<3-(N-Carbethoxy-N-methyl-amino>-propyl>-10,11-dihydro-dibenzocyclohepten-5-ol

72-69-5

3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

Conditions
ConditionsYield
With hydrogen bromide In acetic acid Heating;
3436-04-2

5-(3-bromo-1-propylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

74-89-5

methylamine

72-69-5

3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

Conditions
ConditionsYield
In benzene
In ethanol at 20℃; for 24h;
2939-66-4

10,11-dihydro-5-[3-(methylamino)propyl]-5H-dibenzo[a,d]cyclohepten-5-ol

72-69-5

3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 15h; Heating; Yield given;
50-48-6

Amitriptyline

72-69-5

3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

Conditions
ConditionsYield
With oxygen; palladium on activated charcoal In methanol for 24h; Ambient temperature;
Multi-step reaction with 2 steps
1: benzene / Heating
2: KOH / butan-1-ol / 120 - 125 °C
View Scheme
Multi-step reaction with 2 steps
1: Py / Heating
2: HBr, AcOH, PhOH
View Scheme
With CYP2C19 Enzymatic reaction;
Multi-step reaction with 2 steps
1: triethylamine / 1,2-dichloro-ethane / 2 h / Reflux
2: 4 h / Reflux
View Scheme
50-48-6

Amitriptyline

A

72-69-5

3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

B

1159-82-6

(Z)-N,N-dimethyl-3-(10,11-dihydro-10-hydroxy-5H-dibenzocycloheptene)-Δ5,γ-propylamine

C

64520-05-4, 129312-48-7, 129312-49-8

(-)-(E)-10-Hydroxy-Amitriptylline

Conditions
ConditionsYield
With glucose-6-phosphate dehydrogenase; Tris-HCl buffer; α-D-glucose 6-phosphate; liver microsomes of Wistar rats; NADPH; magnesium chloride In water at 37℃; Rate constant; Product distribution;
115107-86-3

3-(5-Hydroxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-N-methyl-propionamide

72-69-5

3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: LiAlH4 / tetrahydrofuran / 1.) reflux, 4 h, 2.) r.t., 15 h
2: p-TosOH / toluene / 15 h / Heating
View Scheme

Nortriptyline Chemical Properties

Empirical Formula: C19H21N
Molecular Weight: 263.3767 g/mol
EINECS: 200-788-8 
Index of Refraction: 1.633
Density: 1.084 g/cm3
Flash Point: 194.9 °C
Enthalpy of Vaporization: 65.47 kJ/mol
Boiling Point: 403.4 °C at 760 mmHg
Vapour Pressure: 1.02E-06 mmHg at 25 °C 
Structure of Nortriptyline (CAS NO.72-69-5):
               
 

Nortriptyline Uses

  Nortriptyline (CAS NO.72-69-5) is used in the treatment of major depression and childhood nocturnal enuresis (bedwetting), and it is sometimes used for chronic illnesses such as chronic pain and migraines, chronic fatigue syndrome, and labile affect in some neurological conditions.
 

Nortriptyline Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 70mg/kg (70mg/kg)   Journal of Medicinal Chemistry. Vol. 6, Pg. 338, 1963.
mouse LD50 intravenous 17mg/kg (17mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) Journal of Medicinal Chemistry. Vol. 17, Pg. 65, 1974.
mouse LD50 oral 370mg/kg (370mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Arzneimittel-Forschung. Drug Research. Vol. 20, Pg. 1561, 1970.
rat LD50 intravenous 22mg/kg (22mg/kg) BEHAVIORAL: MUSCLE WEAKNESS
BEHAVIORAL: ATAXIA
BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)		 Handbook of Experimental Pharmacology. Vol. 55, Pg. 527, 1980.
rat LD50 oral 502mg/kg (502mg/kg) BEHAVIORAL: MUSCLE WEAKNESS
BEHAVIORAL: ATAXIA
BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)		 Handbook of Experimental Pharmacology. Vol. 55, Pg. 527, 1980.
women TDLo oral 160mg/kg (160mg/kg) BEHAVIORAL: COMA
VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION
CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE		 Journal of Toxicology, Clinical Toxicology. Vol. 37, Pg. 634, 1999.

Nortriptyline Safety Profile

Poison by ingestion, intraperitoneal, and intravenous routes. When heated to decomposition it emits toxic fumes of NOx.

Nortriptyline Specification

 Nortriptyline ,its cas register number is 72-69-5. It also can be called Aventyl ; Sensoval ; Pamelor; Norpress; Allegron ;and Nortrilen . It is the active metabolite of amitriptyline that is demethylated in the liver. Nortriptyline (CAS NO.72-69-5) is FDA-approved for the treatment of major depression, and is metabolised in the liver by hepatic enzyme CYP2D6. Its most common side effects include dry mouth, sedation, constipation, and increased appetite. An occasional side effect is a rapid or irregular heartbeat. For its off-label use for migraine and headache prophylaxis and treating chronic pain: Treatment is started at very low 10 mg once at night to minimise side-effects.

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