Amitriptyline supplier | CasNO.50-48-6

Name
Amitriptyline
EINECS 200-041-6
CAS No. 50-48-6
Article Data40
CAS DataBase
Density 1.076 g/cm³
Solubility water: 9.7 mg/mL
Melting Point 196-197 °C
Formula C₂₀H₂₃N
Boiling Point 398.2 °C at 760 mmHg
Molecular Weight 277.409
Flash Point 174 °C
Transport Information
Appearance
Safety
Risk Codes R36/37/38
Molecular Structure
Hazard Symbols Xi
Synonyms 5H-Dibenzo[a,d]cycloheptene-D5,g-propylamine, 10,11-dihydro-N,N-dimethyl- (6CI,8CI);5-(g-Dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene;Adepress;Amitriptylin;Damilen;MK 230;N 750;Proheptadiene;Seroten;Triptanol;Triptisol;
PSA 3.24000
LogP 4.97060

Synthetic route

: 4317-14-0
Amitriptyline N-oxide

: 50-48-6
Amitriptyline

Conditions

Conditions	Yield
With sodium tetrahydroborate In water at 50 - 60℃; chemoselective reaction;	98%

: 50-00-0
formaldehyd

: 4444-42-2
Desmethylnortriptyline

: 50-48-6
Amitriptyline

Conditions

Conditions	Yield
With formic acid; triethylamine In water; tert-butyl alcohol at 100℃; for 14h;	89%

: 1159-03-1
5-(3-dimethylaminopropyl)-10,11-dihydrodibenzo[a,d]cyclohepten-5-ol

: 50-48-6
Amitriptyline

Conditions

Conditions	Yield
In ethanol at 200℃; under 82508.3 Torr; for 0.01h; Solvent; Temperature; Flow reactor;	78%

: 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.

: N,N-dimethyl-4-(2-phenethylphenyl)but-3-yn-1-amine

: 50-48-6
Amitriptyline

Conditions

Conditions	Yield
With trifluorormethanesulfonic acid In dichloromethane at 0℃; for 0.166667h; Friedel-Crafts Alkylation; regioselective reaction;	56%

: 3433-80-5
1-Bromo-2-bromomethyl-benzene

: 50-48-6
Amitriptyline

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: n-butyllithium; carbon dioxide / tetrahydrofuran; hexane / -50 - 20 °C / 3878.71 Torr / Flow reactor 2: methanol / tetrahydrofuran; toluene / 20 °C / Flow reactor 3: ethanol / 0.01 h / 200 °C / 82508.3 Torr / Flow reactor View Scheme
Multi-step reaction with 3 steps 1: n-butyllithium; carbon dioxide / tetrahydrofuran; hexane / -50 - 20 °C / Flow reactor 2: methanol / tetrahydrofuran; toluene / 20 °C / Flow reactor 3: ethanol / 0.01 h / 200 °C / 82508.3 Torr / Flow reactor View Scheme

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

: 50-48-6
Amitriptyline

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: methanol / tetrahydrofuran; toluene / 20 °C / Flow reactor 2: ethanol / 0.01 h / 200 °C / 82508.3 Torr / Flow reactor View Scheme

: 64-18-6
formic acid

: 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 platinum(0)-1,3-divinyl-1,1,3,3-tetramethyldisiloxane complex; 1,3-bis-(diphenylphosphino)propane; phenylsilane In dibutyl ether at 60℃; for 18h; Schlenk technique; Inert atmosphere;	94 %Chromat.

: C19H20O3S

: 50-48-6
Amitriptyline

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

: 50-48-6
Amitriptyline

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

: 50-48-6
Amitriptyline

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

: 50-48-6
Amitriptyline

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

: 50-48-6
Amitriptyline

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

: 50-48-6
Amitriptyline

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

: 50-48-6
Amitriptyline

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

Conditions

Conditions	Yield
With 2,4,4-trimethyl oxazoline; [2,2]bipyridinyl; C10H16NO; copper(II) bis(trifluoromethanesulfonate); copper(l) chloride In acetonitrile at 20℃; for 24h;	94%

: 27550-73-8
Chloromethyl methacrylate

: 50-48-6
Amitriptyline

: 76637-17-7
[3-(10,11-Dihydro-dibenzo[a,d]cyclohepten-5-ylidene)-propyl]-dimethyl-(2-methyl-acryloyloxymethyl)-ammonium; chloride

Conditions

Conditions	Yield
In chloroform	87%

: 50-48-6
Amitriptyline

: 73037-99-7
3-(10,11-Dihydro-5-fluoro-5H-dibenzocyclohepten-5-yl)-3-fluoro-1-N,N-dimethylpropanamine

Conditions

Conditions	Yield
With pyridinium polyhydrogenfluoride; dimethyl 2,2'-((2-iodo-5-(methoxycarbonyl)-1,3-phenylene)bis(oxy))diacetate; 3-chloro-benzenecarboperoxoic acid at 20℃; for 12h; Sealed tube;	41%
With hypofluorous acid trifluoromethyl ester In dichloromethane at -50℃;	5%

: 50-48-6
Amitriptyline

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

: 86492-47-9
((2R,3R,4S,5S,6S)-6-Carboxy-3,4,5-trihydroxy-tetrahydro-pyran-2-yl)-[3-(10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidene)-propyl]-dimethyl-ammonium; chloride

Conditions

Conditions	Yield
With XAD-2 ion-exchange resin; sodium hydrogencarbonate In water; benzene for 72h; Ambient temperature;	36%

: potassium cyanide

: 50-48-6
Amitriptyline

: 2-((3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)propyl)(methyl)amino)acetonitrile

Conditions

Conditions	Yield
With 2-Picolinic acid; iron(III) chloride; tert-Butyl peroxybenzoate; 18-crown-6 ether In acetonitrile at 50℃; for 48h;	35%

: 506-68-3
bromocyane

: 50-48-6
Amitriptyline

: 17684-48-9
5-(3-N-Cyano-N-methylaminopropylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

: 50-48-6
Amitriptyline

: 24755-73-5
5-(2-propenylidene)-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Conditions

Conditions	Yield
(i) MeI, (ii) aq. NaOH; Multistep reaction;

: 50-48-6
Amitriptyline

: 16234-91-6
5-<3-(N-Sulfonato-N,N-dimethyl-ammonio)-propyliden>-10,11-dihydro-dibenzocyclohepten

Conditions

Conditions	Yield
With ethyl chlorosulfate In benzene Heating;

: 50-48-6
Amitriptyline

: 541-41-3
chloroformic acid ethyl ester

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

Conditions

Conditions	Yield
In benzene Heating;

: 50-48-6
Amitriptyline

: 108-24-7
acetic anhydride

: 16234-90-5
N-acetylnortriptyline

Conditions

Conditions	Yield
With aluminium trichloride Heating;

: 50-48-6
Amitriptyline

: 98-59-9
p-toluenesulfonyl chloride

: 16235-12-4
5-<3-(N-Methyl-p-toluolsulfonamido)-propyliden>-10,11-dihydro-dibenzocyclohepten

Conditions

Conditions	Yield
With pyridine Heating;

: 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

: 50-48-6
Amitriptyline

: 4444-42-2
Desmethylnortriptyline

Conditions

Conditions	Yield
With cDNA-expressed human cytochrome P450 (CYP) 1A2 enzyme In water at 37℃; for 0.25h; pH=7.4; Enzyme kinetics; Further Variations:; Reagents; demethylation; Enzymatic reaction;
Multi-step reaction with 2 steps 1: CYP2C19 / Enzymatic reaction 2: CYP2C19 / Enzymatic reaction View Scheme

: 50-48-6
Amitriptyline

: 64520-05-4, 129312-48-7, 129312-49-8
(-)-(E)-10-Hydroxy-Amitriptylline

Conditions

Conditions	Yield
With cDNA-expressed human cytochrome P450 (CYP) 2D6 enzyme In water at 37℃; for 0.25h; pH=7.4; Enzyme kinetics; Further Variations:; Reagents; hydroxylation; Enzymatic reaction;

: 50-48-6
Amitriptyline

: 76-99-3
Methadone

: (R,S)-2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine

Conditions

Conditions	Yield
With human CYP2D6 In phosphate buffer at 37℃; for 0.333333h; pH=7.4; Enzyme kinetics;
With human CYP3A4 In phosphate buffer at 37℃; for 0.333333h; pH=7.4; Enzyme kinetics;

: 50-48-6
Amitriptyline

: 4317-14-0
Amitriptyline N-oxide

Conditions

Conditions	Yield
With dihydrogen peroxide In methanol for 168h;	2.2 g

: 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

: 50-48-6
Amitriptyline

: 549-18-8
amitriptyline hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In isopropyl alcohol at 20℃; Flow reactor;

Amitriptyline Chemical Properties

Molecular Structure:

Molecular Formula: C₂₀H₂₃N
Molecular Weight: 277.4033
IUPAC Name: (3S,4R)-3-(1,3-Benzodioxol-5-yloxymethyl)-4-(4-fluorophenyl)piperidine
Synonyms of Amitriptyline (CAS NO.50-48-6): 10,11-Dihydro-5-(gamma-dimethylaminopropylidene)-5H-dibenzo(a,d)cycloheptene ; 10,11-Dihydro-N,N-dimethyl-5H-dibenzo(a,d)heptalene-delta(sup 5),gamma-propylamine ; 3-(10,11-Dihydro-5H-dibenzo(a,d)cyclohepten-5-yliden)-N,N-dimethylpropylamin ; 3-(10,11-Dihydro-5H-dibenzo(a,d)cyclohepten-5-ylidene)-N,N-dimethyl-1-propanamine ; 5-(3'-Dimethylaminopropylidene)-dibenzo-(a,d)(1,4)-cycloheptadiene ; 5-(3-Dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo(a,d)cycloheptene ; 5-(gamma-Dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo(a,d)cycloheptene ; 5-(gamma-Dimethylaminopropylidine)-5H-dibenzo(a,d)(1,4)cycloheptadiene ; 5H-Dibenzo(a,d)cycloheptene-delta5,gamma-propylamine, 10,11-dihydro-N,N-dimethyl- ; Adepress ; Adepril ; Amitriptilina ; Amitriptilina [INN-Spanish] ; Amitriptilina [Italian] ; Amitriptylin ; Amitriptylin [German] ; Amitriptylinum ; Amitriptylinum [INN-Latin] ; Amytriptylin ; BRN 2217885 ; CCRIS 9174 ; Damilen ; Damitriptyline ; EINECS 200-041-6 ; Elavil ; Flavyl ; Lantron ; MK 230 ; N 750 ; Proheptadiene ; Redomex ; Ro 4-1575 ; Seroten ; Triptanol ; Triptilin ; Triptisol ; Tryptanol ; UNII-1806D8D52K ; 1-Propanamine, 3-(10,11-dihydro-5H-dibenzo(a,d)cyclohepten-5-ylidene)-N,N-dimethyl- ; 5H-Dibenzo(a,d)cycloheptene-delta(sup 5),gamma-propylamine, 10,11-dihydro-N,N-dimethyl-
CAS NO: 50-48-6
Classification Code: Adrenergic Agents ; Adrenergic uptake inhibitors ; Analgesics ; Analgesics, Non-Narcotic ; Antidepressive Agents ; Antidepressive agents, tricyclic ; Antihistaminic ; Central Nervous System Agents ; Drug / Therapeutic Agent ; Human Data ; Neurotransmitter Agents ; Neurotransmitter Uptake Inhibitors ; Peripheral Nervous System Agents ; Psychotropic Drugs ; Reproductive Effect ; Sensory System Agents
Melting point: 196-197°C
Index of Refraction: 1.628
Molar Refractivity: 91.52 cm³
Molar Volume: 257.7 cm³
Surface Tension: 47 dyne/cm
Density: 1.076 g/cm³
Flash Point: 174 °C
Enthalpy of Vaporization: 64.88 kJ/mol
Boiling Point: 398.2 °C at 760 mmHg
Vapour Pressure: 1.5E-06 mmHg at 25°C

Amitriptyline Uses

Amitriptyline (CAS NO.50-48-6) is recommended for the treatment of mental depression, with improvement in mood seen in 2 to 3 weeks after the start of medication. It is now used in the United States and United Kingdom to prevent migraines only in very small doses. It is also used as sleeping aids in small doses of usually 25 mg, and for diabetic retinopathy.

Amitriptyline Production

The synthesis of Amitriptyline (CAS NO.50-48-6) starts from the key intermediate dibenzo-suberone (manufactured from phthalic anhydride) and can proceed by two pathways (Fig. 1). Treatment of dibenzosuberone with cyclopropyl Grignard gives the tertiary alcohol after hydrolysis. Reaction of the alcohol with hydrochloric acid proceeds with rearrangement and opening of the strained cyclopropane to give a chloride. Reaction and displacement of the chlorine atom with dimethylamine forms amitriptyline. Alternatively, dibenzosuberone can be reacted with dimethylaminopropyl Grignard to form an alcohol, which upon dehydration forms amitriptyline.

FIGURE 1 Manufacture of amitriptyline.

Amitriptyline Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
child	TDLo	oral	4500ug/kg (4.5mg/kg)	BEHAVIORAL: SLEEP	British Medical Journal. Vol. 3, Pg. 663, 1967.
dog	LDLo	subcutaneous	50mg/kg (50mg/kg)	PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Pharmacologist. Vol. 11, Pg. 283, 1969.
guinea pig	LDLo	intravenous	35mg/kg (35mg/kg)		Drugs of the Future. Vol. 8, Pg. 949, 1983.
human	TDLo	oral	2mg/kg/3D-I (2mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: CHANGES IN PSYCHOPHYSIOLOGICAL TESTS	British Journal of Clinical Pharmacology. Vol. 49, Pg. 118, 2000.
human	TDLo	oral	14mg/kg (14mg/kg)	CARDIAC: OTHER CHANGES	Proceedings of the European Society for the Study of Drug Toxicity. Vol. 6, Pg. 171, 1965.
infant	TDLo	oral	50mg/kg (50mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD CARDIAC: CHANGE IN RATE BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)	American Journal of Diseases of Children. Vol. 130, Pg. 507, 1976.
man	LDLo	oral	29mg/kg (29mg/kg)		Human & Experimental Toxicology. Vol. 9, Pg. 257, 1990.
man	TDLo	oral	1564mg/kg/2Y- (1564mg/kg)	PERIPHERAL NERVE AND SENSATION: PARESTHESIS BEHAVIORAL: ATAXIA BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)	Italian Journal of Neurological Sciences. Vol. 9, Pg. 89, 1988.
man	TDLo	unreported	45mg/kg/21D (45mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) CARDIAC: CHANGE IN RATE	Lancet. Vol. 2, Pg. 1202, 1972.
mouse	LD50	intraperitoneal	48400ug/kg (48.4mg/kg)		Farmakologiya i Toksikologiya Vol. 53(4), Pg. 19, 1990.
mouse	LD50	intravenous	16mg/kg (16mg/kg)	BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)	Journal of Medicinal Chemistry. Vol. 17, Pg. 65, 1974.
mouse	LD50	oral	99mg/kg (99mg/kg)		Doklady Akademii Nauk SSSR. Proceedings of the Academy of Sciences of the USSR. For English translation, see DBIOAM and DKBSAS. Vol. 335, Pg. 388, 1994.
mouse	LD50	subcutaneous	100mg/kg (100mg/kg)		United States Patent Document. Vol. #4605673,
mouse	LD50	unreported	80mg/kg (80mg/kg)	AUTONOMIC NERVOUS SYSTEM: "SMOOTH MUSCLE RELAXANT (MECHANISM UNDEFINED, SPASMOLYTIC)"	Journal of Medicinal Chemistry. Vol. 10, Pg. 418, 1967.
rabbit	LD50	intraperitoneal	58700ug/kg (58.7mg/kg)	LUNGS, THORAX, OR RESPIRATION: CYANOSIS	Journal of Toxicology, Clinical Toxicology. Vol. 19, Pg. 321, 1982.
rabbit	LD50	intravenous	8600ug/kg (8.6mg/kg)		Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 863, 1965.
rat	LD50	intraperitoneal	72mg/kg (72mg/kg)		Polish Journal of Pharmacology and Pharmacy. Vol. 27, Pg. 503, 1975.
rat	LD50	oral	320mg/kg (320mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) GASTROINTESTINAL: CHANGES IN STRUCTURE OR FUNCTION OF SALIVARY GLANDS BEHAVIORAL: ATAXIA	Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 863, 1965.
women	TDLo	intramuscular	240ug/kg/36H- (0.24mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Lancet. Vol. 1, Pg. 390, 1968.
women	TDLo	oral	13500ug/kg/3D (13.5mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: EXCITEMENT	Lancet. Vol. 1, Pg. 390, 1968.
women	TDLo	oral	16800ug/kg/2W (16.8mg/kg)	PERIPHERAL NERVE AND SENSATION: PARESTHESIS BEHAVIORAL: HEADACHE	Lancet. Vol. 1, Pg. 426, 1968.
women	TDLo	oral	18500ug/kg (18.5mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 35, Pg. 795, 1993.
women	TDLo	oral	60mg/kg (60mg/kg)	CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION) CARDIAC: CHANGE IN RATE VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION	Journal of Toxicology, Clinical Toxicology. Vol. 19, Pg. 67, 1982.
women	TDLo	oral	84mg/kg (84mg/kg)	CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE	Japanese Journal of Toxicology. Vol. 5, Pg. 69, 1992.

Amitriptyline Safety Profile

Human poison by an unspecified route. Poison experimentally by ingestion, intraperitoneal, subcutaneous, intramuscular, and intravenous routes. Human systemic effects by ingestion and intramuscular routes: changes in sleep, headache, paresthesia, convulsions, excitement, somnolence, muscle contractions, change in heart rate, and other cardiac changes. An experimental teratogen. Other experimental reproductive effects. An antidepressant. When heated to decomposition it emits toxic fumes of NO_x.

Amitriptyline Specification

Common side effects of using amitriptyline are mostly due to its anticholinergic activity, including: weight gain, dry mouth, loss of appetite, drowsiness, muscle stiffness, nausea, constipation, nervousness, dizziness, blurred vision, urinary retention and insomnia. Some rare side effects include tinnitus, hypotension, mania, psychosis, heart block, arrhythmias, lip and mouth ulcers, extrapyramidal symptoms, depression, and hepatic toxicity.

Product Name

Amitriptyline

Synthetic route

Amitriptyline Chemical Properties

Amitriptyline Uses

Amitriptyline Production

Amitriptyline Toxicity Data With Reference

Amitriptyline Safety Profile

Amitriptyline Specification

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