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CAS No.: | 72-69-5 |
---|---|
Name: | NORTRIPTYLINE |
Article Data: | 34 |
Molecular Structure: | |
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 |
amitriptyline hydrochloride
A
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine
B
10-Hydroxynortriptyline
C
(Z)-10-Hydroxyamitriptyline
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 |
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine
Conditions | Yield |
---|---|
With trifluorormethanesulfonic acid In dichloromethane at 0℃; for 0.166667h; Friedel-Crafts Alkylation; regioselective reaction; | 68% |
5-<3-(N-Carbethoxy-N-methyl-amino)-propyliden>-10,11-dihydro-dibenzocyclohepten
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine
Conditions | Yield |
---|---|
With potassium hydroxide In butan-1-ol at 120 - 125℃; |
5-<3-(N-Methyl-p-toluolsulfonamido)-propyliden>-10,11-dihydro-dibenzocyclohepten
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine
Conditions | Yield |
---|---|
With hydrogen bromide; acetic acid; phenol |
5-<3-(N-Carbethoxy-N-methyl-amino>-propyl>-10,11-dihydro-dibenzocyclohepten-5-ol
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine
Conditions | Yield |
---|---|
With hydrogen bromide In acetic acid Heating; |
5-(3-bromo-1-propylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene
methylamine
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine
Conditions | Yield |
---|---|
In benzene | |
In ethanol at 20℃; for 24h; |
10,11-dihydro-5-[3-(methylamino)propyl]-5H-dibenzo[a,d]cyclohepten-5-ol
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In toluene for 15h; Heating; Yield given; |
Amitriptyline
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine
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 |
Amitriptyline
A
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine
B
(Z)-N,N-dimethyl-3-(10,11-dihydro-10-hydroxy-5H-dibenzocycloheptene)-Δ5,γ-propylamine
C
(-)-(E)-10-Hydroxy-Amitriptylline
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; |
3-(5-Hydroxy-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-yl)-N-methyl-propionamide
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine
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 |
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 (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.
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. |
Poison by ingestion, intraperitoneal, and intravenous routes. When heated to decomposition it emits toxic fumes of NOx.
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.