Nortriptyline supplier | CasNO.72-69-5

Name
NORTRIPTYLINE
EINECS 200-788-8
CAS No. 72-69-5
Article Data34
CAS DataBase
Density 1.084 g/cm³
Solubility
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
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
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;
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

: 99082-15-2
3',4',10,11-Tetrahydro-spiro<5H-dibenzocyclohepten-5,5'(2'H)-furan>-2'-on

: 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 3 steps 1: ethanol / 72 h / Ambient temperature 2: LiAlH4 / tetrahydrofuran / 1.) reflux, 4 h, 2.) r.t., 15 h 3: p-TosOH / toluene / 15 h / Heating View Scheme

: 3436-04-2
5-(3-bromo-1-propylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

: 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: 170 °C 2: HBr, AcOH, PhOH View Scheme

: 1159-03-1
5-(3-dimethylaminopropyl)-10,11-dihydrodibenzo[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
Multi-step reaction with 2 steps 1: benzene / Heating 2: aq. HBr / acetic acid / Heating View Scheme

: 2-[3-(10,11-Dihydro-dibenzo[a,d]cyclohepten-5-ylidene)-propoxy]-tetrahydro-pyran

: 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 3 steps 1: aq. HBr / Heating 2: 170 °C 3: HBr, AcOH, PhOH View Scheme
Multi-step reaction with 2 steps 1: aq. HBr / Heating 2: benzene View Scheme

: aminomethylfluorescein hydrochloride

: 4156-16-5
2-ethyl-5-phenylisoxazolium-3'-sulphonate

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

Conditions

Conditions	Yield
With triethylamine; trifluoroacetic acid In dichloromethane; N,N-dimethyl-formamide

: 50-48-6
Amitriptyline

A: hydroxy-amitriptyline

B: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

C: 4444-42-2
Desmethylnortriptyline

D: 37401-47-1
N,Ndimethyl-3-(10,11-dihydro-10-oxo-5H-dibenzocycloheptene)-Δ5,γ-propylamine

Conditions

Conditions	Yield
With NADPH In water; dimethyl sulfoxide at 37℃; for 1h; Microbiological reaction;

...Expand

: 40443-02-5
3-(10,11-dihydro-5H-dibenzocyclohepten-5-ylidene)propionitrile

: 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 1.1: lithium aluminium tetrahydride / tetrahydrofuran 2.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.33 h 2.2: 4 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.33 h / Inert atmosphere; Cooling with ice 2.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C 2.2: 4 h / 20 °C View Scheme

: 4444-42-2
Desmethylnortriptyline

: 74-88-4
methyl iodide

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

Conditions

Conditions	Yield
Stage #1: Desmethylnortriptyline With sodium hydride In N,N-dimethyl-formamide; mineral oil for 0.333333h; Stage #2: methyl iodide In N,N-dimethyl-formamide; mineral oil at 20℃; for 4h;
Stage #1: Desmethylnortriptyline With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.333333h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 4h;

: 55090-31-8
5-ethyl-10,11-dihydro-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
Multi-step reaction with 5 steps 1.1: acetyl chloride / 1.5 h / Reflux 2.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 4 h / Reflux 3.1: acetone; water / 12 h / Reflux 4.1: lithium aluminium tetrahydride / tetrahydrofuran 5.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.33 h 5.2: 4 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1.1: acetyl chloride / 1.5 h / Reflux 2.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 4 h / Reflux 3.1: acetone; water / 12 h / Reflux 4.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.33 h / Inert atmosphere; Cooling with ice 5.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C 5.2: 4 h / 20 °C View Scheme

: 28860-39-1
5-Ethyliden-10,11-dihydro-5H-dibenzocycloheptan

: 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 4 steps 1.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 4 h / Reflux 2.1: acetone; water / 12 h / Reflux 3.1: lithium aluminium tetrahydride / tetrahydrofuran 4.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.33 h 4.2: 4 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 4 h / Reflux 2.1: acetone; water / 12 h / Reflux 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.33 h / Inert atmosphere; Cooling with ice 4.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C 4.2: 4 h / 20 °C View Scheme

: 13099-16-6
2-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)ethyl bromide

: 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 3 steps 1.1: acetone; water / 12 h / Reflux 2.1: lithium aluminium tetrahydride / tetrahydrofuran 3.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 0.33 h 3.2: 4 h / 20 °C View Scheme
Multi-step reaction with 3 steps 1.1: acetone; water / 12 h / Reflux 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.33 h / Inert atmosphere; Cooling with ice 3.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C 3.2: 4 h / 20 °C View Scheme

: C19H20O3S

: 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: ethanol; water / 2 h / 50 °C 2: trifluorormethanesulfonic acid / dichloromethane / 0.17 h / 0 °C View Scheme

: 583-55-1
1-Bromo-2-iodobenzene

: 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 6 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) iodide / acetonitrile / 22 h / 0 - 20 °C 2: hydrogen; palladium 10% on activated carbon / ethyl acetate / 6 h / 20 °C 3: caesium carbonate; dichloro bis(acetonitrile) palladium(II); dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / acetonitrile / 6.5 h / 60 °C 4: triethylamine / dichloromethane / 2.5 h / 0 °C 5: ethanol; water / 2 h / 50 °C 6: trifluorormethanesulfonic acid / dichloromethane / 0.17 h / 0 °C View Scheme

Yield

Multi-step reaction with 6 steps
1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) iodide / acetonitrile / 22 h / 0 - 20 °C
2: hydrogen; palladium 10% on activated carbon / ethyl acetate / 6 h / 20 °C
3: caesium carbonate; dichloro bis(acetonitrile) palladium(II); dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / acetonitrile / 6.5 h / 60 °C
4: triethylamine / dichloromethane / 2.5 h / 0 °C
5: ethanol; water / 2 h / 50 °C
6: trifluorormethanesulfonic acid / dichloromethane / 0.17 h / 0 °C
View Scheme

: 21375-88-2
1-bromo-2-(phenylethenyl)benzene

: 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 5 steps 1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 6 h / 20 °C 2: caesium carbonate; dichloro bis(acetonitrile) palladium(II); dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / acetonitrile / 6.5 h / 60 °C 3: triethylamine / dichloromethane / 2.5 h / 0 °C 4: ethanol; water / 2 h / 50 °C 5: trifluorormethanesulfonic acid / dichloromethane / 0.17 h / 0 °C View Scheme

Yield

Multi-step reaction with 5 steps
1: hydrogen; palladium 10% on activated carbon / ethyl acetate / 6 h / 20 °C
2: caesium carbonate; dichloro bis(acetonitrile) palladium(II); dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / acetonitrile / 6.5 h / 60 °C
3: triethylamine / dichloromethane / 2.5 h / 0 °C
4: ethanol; water / 2 h / 50 °C
5: trifluorormethanesulfonic acid / dichloromethane / 0.17 h / 0 °C
View Scheme

: 57918-64-6
1-(2-bromophenyl)-2-phenylethane

: 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 4 steps 1: caesium carbonate; dichloro bis(acetonitrile) palladium(II); dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / acetonitrile / 6.5 h / 60 °C 2: triethylamine / dichloromethane / 2.5 h / 0 °C 3: ethanol; water / 2 h / 50 °C 4: trifluorormethanesulfonic acid / dichloromethane / 0.17 h / 0 °C View Scheme

: 4-(2-phenethylphenyl)but-3-yn-1-ol

: 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 3 steps 1: triethylamine / dichloromethane / 2.5 h / 0 °C 2: ethanol; water / 2 h / 50 °C 3: trifluorormethanesulfonic acid / dichloromethane / 0.17 h / 0 °C View Scheme

: 536-74-3
phenylacetylene

: 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 6 steps 1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) iodide / acetonitrile / 22 h / 0 - 20 °C 2: hydrogen; palladium 10% on activated carbon / ethyl acetate / 6 h / 20 °C 3: caesium carbonate; dichloro bis(acetonitrile) palladium(II); dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / acetonitrile / 6.5 h / 60 °C 4: triethylamine / dichloromethane / 2.5 h / 0 °C 5: ethanol; water / 2 h / 50 °C 6: trifluorormethanesulfonic acid / dichloromethane / 0.17 h / 0 °C View Scheme

Yield

: 1210-35-1
10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-one

: 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 6 steps 1.1: diethyl ether / 1.25 h / 20 °C / Reflux 2.1: acetyl chloride / 1.5 h / Reflux 3.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 4 h / Reflux 4.1: acetone; water / 12 h / Reflux 5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.33 h / Inert atmosphere; Cooling with ice 6.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C 6.2: 4 h / 20 °C View Scheme

Yield

Multi-step reaction with 6 steps
1.1: diethyl ether / 1.25 h / 20 °C / Reflux
2.1: acetyl chloride / 1.5 h / Reflux
3.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 4 h / Reflux
4.1: acetone; water / 12 h / Reflux
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.33 h / Inert atmosphere; Cooling with ice
6.1: sodium hydride / N,N-dimethyl-formamide / 0.33 h / 0 °C
6.2: 4 h / 20 °C
View Scheme

: 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: 64520-05-4
(Z)-10-Hydroxyamitriptyline

Conditions

Conditions	Yield
With glucose dehydrogenase; D-glucose; cytochrome P450BM3 R47L/Y51F/V78I/A191T/N239H/I259V/A276T/A330P/L353I mutant; oxygen; β-nicotinamide adenine dinucleotide phosphate sodium salt In ethanol at 25℃; for 2h; pH=8.5; Enzymatic reaction;	A n/a B 18.7 mg

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: 1111-72-4
carbon dioxide

: [N-13CH3]-amitriptyline

Conditions

Conditions	Yield
With hydrogen; tris(acetylacetonato)ruthenium(III); lithium chloride; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran at 140℃; for 20h; Autoclave; Inert atmosphere;	96%

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: 140-88-5
ethyl acrylate

: 3-{[3-(10,11-Dihydro-dibenzo[a,d]cyclohepten-5-ylidene)-propyl]-methyl-amino}-propionic acid ethyl ester

Conditions

Conditions	Yield
In ethanol for 2h; Heating;	95%

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: 76-05-1
trifluoroacetic acid

: 3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)-N-methyl-N-(2,2,2-trifluoroethyl)propan-1-amine

Conditions

Conditions	Yield
With potassium phosphate; 18-crown-6 ether; phenylsilane In tetrahydrofuran at 80℃; for 4h; Glovebox; Molecular sieve; Schlenk technique;	94%

: 1006904-72-8
silver(I) trifluoromethoxide

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: (3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)propyl)(methyl)carbamic fluoride

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 20℃; for 2h; Inert atmosphere;	93%

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: 776-74-9
Bromodiphenylmethane

: N-benzhydryl-3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)-N-methylpropan-1-amine

Conditions

Conditions	Yield
With triethylamine In acetonitrile at 100℃; for 12h; Inert atmosphere;	91%

: 5061-21-2
α-bromo-γ-butyrolactone

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: 3-[methyl(3-{tricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,12,14- hexaen-2-ylidene}propyl)amino]oxolan-2-one

Conditions

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In acetonitrile at 0 - 20℃;	89%

: 124-38-9
carbon dioxide

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: 75-03-6
ethyl iodide

: 16234-88-1
5-<3-(N-Carbethoxy-N-methyl-amino)-propyliden>-10,11-dihydro-dibenzocyclohepten

Conditions

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 20℃; chemoselective reaction;	86%

...Expand

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: 1-((3,5-difluorophenyl)sulfonyl)bicyclo[1.1.0]butane

: C23H27N

Conditions

Conditions	Yield
Stage #1: 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine; 1-((3,5-difluorophenyl)sulfonyl)bicyclo[1.1.0]butane In dimethyl sulfoxide at 20℃; for 24h; Sonication; Stage #2: With magnesium In deuteromethanol	83%

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: 2-iodo-4,N-dimethyl-N-phenylethynylbenzenesulfonamide

: C35H34N2O2S

Conditions

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In dimethyl sulfoxide at 70℃; for 12h; Schlenk technique; Inert atmosphere; Sealed tube;	76%

: 124-38-9
carbon dioxide

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: N-(3-(10,11-dihydro-5H-dibenso[a,d][7]annulen-5-ylidene)propyl)-N-methylformamide

Conditions

Conditions	Yield
With phenylsilane; tetrabutyl ammonium fluoride at 20℃; for 4h;	70%

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: 1621341-90-9
2-bromo-N-(4-chlorobenzyl)-4-(1,3-dioxoisoindolin-2-yl)butanamide

: N-[(4-chlorophenyl)methyl]-4-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-2-[methyl(3-{tricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,12,14-hexaen-2-ylidene}propyl)amino]butanamide

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Reflux;	64%

: 124-38-9
carbon dioxide

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: 50-48-6
Amitriptyline

Conditions

Conditions	Yield
With diphenylsilane; [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene In N,N-dimethyl-formamide at 50℃; under 760.051 Torr; chemoselective reaction;	63%
With hydrogen; tris(acetylacetonato)ruthenium(III); lithium chloride; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran at 140℃; for 24h; Autoclave; Inert atmosphere;	81 %Chromat.

: 59337-89-2
3-chlorothiophene-2-carboxylic acid

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: 1067431-34-8
3-chloro-N-[3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)propyl]-N-methylthiophene-2-carboxamide

Conditions

Conditions	Yield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;	56%

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: 58537-73-8
1-oxyl-2,2,5,5-tetramethylpyrrolidinyl-3-carboxylic acid N-hydroxysuccinimide ester

A: C28H35N2O2

B: C32H40N3O5

Conditions

Conditions	Yield
In tetrahydrofuran 1) 4d, RT, 2) 50-60 deg C, 3 d;	A 55% B 29%

...Expand

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: 130-15-4
[1,4]naphthoquinone

: 2-cyclohepten-5-yliden)-propylamino>-1,4-naphthochinon

Conditions

Conditions	Yield
In dichloromethane for 1h; Ambient temperature; in the dark;	54%

: 16699-70-0
N-benzyl-2-bromo-4-(1,3-dioxoisoindolin-2-yl)butanamide

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: N-benzyl-4-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-2-[methyl(3-{tricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,12,14-hexaen-2-ylidene}propyl)amino]butanamide

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Reflux;	52%

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: 553-97-9
2-Methyl-1,4-benzoquinone

A: 108141-74-8
5-Methyl-2-cyclohepten-5-yliden)-propylamino>-1,4-benzochinon

B: 108141-78-2
6-Methyl-2-cyclohepten-5-yliden)-propylamino>-1,4-benzochinon

Conditions

Conditions	Yield
In dichloromethane for 24h; Ambient temperature;	A 51% B 34%

...Expand

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: 54325-28-9
6-O-trityl-D-glucopyranose

A: N-[6-O-trityl-D-glucopyranosyl]-N-methyl-3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-propanamine

B: 1186033-19-1
N-[6-O-trityl-β-D-glucopyranosyl]-N-methyl-3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-propanamine

Conditions

Conditions	Yield
In dichloromethane at 20℃; Inert atmosphere;	A n/a B 49%

...Expand

: 117-80-6
2,3-Dichloro-1,4-naphthoquinone

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: 3-Chlor-2-cyclohepten-5-yliden)-propylamino>-1,4-naphthochinon

Conditions

Conditions	Yield
In dichloromethane for 2h;	48%

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: 1621341-88-5
2-bromo-N-(2-chlorobenzyl)-4-(1,3-dioxoisoindolin-2-yl)butanamide

: N-[(2-chlorophenyl)methyl]-4-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-2-[methyl(3-{tricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,12,14-hexaen-2-ylidene}propyl)amino]butanamide

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Reflux;	47%

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: 1621341-92-1
2-bromo-4-(1,3-dioxoisoindolin-2-yl)-N-(4-fluorobenzyl)butanamide

: N-[(4-fluorophenyl)methyl]-4-(1,3-dioxo-2,3-dihydro-1Hisoindol-2-yl)-2-[methyl(3-{tricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,12,14-hexaen-2-ylidene}propyl)amino]butanamide

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Reflux;	47%

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: 1621341-94-3
2-bromo-4-(1,3-dioxoisoindolin-2-yl)-N-(4-methylbenzyl)butanamide

: 4-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-2-[methyl(3-{tricyclo[9.4.0.03,8]pentadeca-1(11),3,5,7,12,14-hexaen-2-ylidene}propyl)amino]-N-[(4-methylphenyl)methyl]butanamide

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Reflux;	45%

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: N-Methyl-3-(10,11-dihydro-5H-dibenzocyclohepten-5-yliden)-propylamino-1,4-benzochinon

: 2,5-Bis-cyclohepten-5-yliden)-propylamino>-1,4-benzochinon

Conditions

Conditions	Yield
In dichloromethane Ambient temperature;	44%

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: 13243-65-7
2,3-Dibromo-1,4-naphthoquinone

: 3-Brom-2-cyclohepten-5-yliden)-propylamino>-1,4-naphthochinon

Conditions

Conditions	Yield
In dichloromethane for 1h;	42%

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: 18217-00-0
1-(2-Chloroethyl)-4-methoxybenzene

: 3-(5,6-dihydrodibenzo[2,1-b:1',2'-e][7]annulen-11-ylidene)-N-[2-(4-methoxyphenyl)ethyl]-N-methylpropan-1-amine

Conditions

Conditions	Yield
Stage #1: 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 1-(2-Chloroethyl)-4-methoxybenzene With triisobutylaluminum In tetrahydrofuran; hexane; toluene for 48h; Reflux; Inert atmosphere;	31%

: 27160-08-3
2-(3,4-dimethoxyphenyl)-ethylchloride

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: 3-(5,6-dihydrodibenzo[2,1-b:1',2'-e][7]annulen-11-ylidene)-N-[2-(3,4-dimethoxyphenyl)ethyl]-N-methylpropan-1-amine

Conditions

Conditions	Yield
Stage #1: 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: 2-(3,4-dimethoxyphenyl)-ethylchloride With triisobutylaluminum In tetrahydrofuran; hexane; toluene for 48h; Reflux; Inert atmosphere;	27%

: 72-69-5
3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N-methyl-1-propanamine

: 21085-72-3
1-bromo-2,3,4-tri-O-acetyl-α-D-glucuronic acid methyl ester

A: 62346-09-2
methyl 2-acetoxy-3,4-di-O-acetyl-D-arabino-hex-1-enopyranuronate

B: 1207167-91-6
C32H37NO9

Conditions

Conditions	Yield
With sodium carbonate In dichloromethane; water; acetone	A n/a B 26%

...Expand

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 NO_x.

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.

Product Name

NORTRIPTYLINE

Synthetic route

Nortriptyline Chemical Properties

Nortriptyline Uses

Nortriptyline Toxicity Data With Reference

Nortriptyline Safety Profile

Nortriptyline Specification

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