Name: NORTRIPTYLINE
SKU: 72-69-5

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Basic Information

Molecular Structure:
CAS No.:	72-69-5
Name:	NORTRIPTYLINE

Formula:	C₁₉H₂₁N
Molecular Weight:	263.382
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;
EINECS:	200-788-8
Density:	1.084 g/cm³
Melting Point:	58 °C
Boiling Point:	403.4 °C at 760 mmHg
Flash Point:	194.9 °C
PSA:	12.03000
LogP:	4.21730

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

Conditions	Yield
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

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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;

...Expand

: 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

Conditions	Yield
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

Raw Materials

50-48-6

74-89-5

74-88-4

Downstream Products

50-48-6

Total:53 Page 1 of 2 1 2 Next>>

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Chemistry

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):

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.

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.

Safety Profile

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

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.

72-69-5

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Chemistry

Uses

Toxicity Data With Reference

Safety Profile

Specification