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549-18-8

Basic Information
CAS No.: 549-18-8
Name: Amitriptyline hydrochloride
Article Data: 3
Molecular Structure:
Molecular Structure of 549-18-8 (Amitriptyline hydrochloride)
Formula: C20H23N.HCl
Molecular Weight: 313.87
Synonyms: 1-Propanamine,3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-,hydrochloride (1:1);5H-Dibenzo[a,d]cycloheptene-D5,g-propylamine,10,11-dihydro-N,N-dimethyl-, hydrochloride (6CI,8CI);10,11-Dihydro-N,N-dimethyl-5H-dibenzo[a,d]cycloheptene-D5,g-propylaminehydrochloride;5-(3-Dimethylaminopropylidene)dibenzo[a,d][1,4]cycloheptadienehydrochloride;Adepril;Amicen;Amineurin;Amiplin;Amiprin;Amyline;Anapsique;Tryptine;Trytomer;Vanatrip;Apo-Amitriptyline;Deprex;Domical;Elatrolet;Etravil;Lantron;Miketorin;NIH 10794;Noriline;Novoprotect;Ro 4-1575;Saroten;Saroten Retard;Sarotena;Sylvemid;Triptizol;Trynol;Tryptanol;
EINECS: 208-964-6
Density: 1.076g/cm3
Melting Point: 196-197 °C
Boiling Point: 398.2 °C at 760 mmHg
Flash Point: 174 °C
Solubility: soluble in water
Appearance: white crystalline powder
Hazard Symbols: ToxicT, FlammableF
Risk Codes: 23/24/25-36/37/38-42/43-63-39/23/24/25-11
Safety: 22-26-36/37/39-45-36/37-16
Transport Information: UN 2811 6.1/PG 3
PSA: 3.24000
LogP: 4.97060
Synthetic route
1159-03-1

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

549-18-8

amitriptyline hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In ethanol Heating;63%
Multi-step reaction with 2 steps
1: ethanol / 0.01 h / 200 °C / 82508.3 Torr / Flow reactor
2: hydrogenchloride / isopropyl alcohol / 20 °C / Flow reactor
View Scheme
1210-35-1

10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-one

109-54-6

3-(Dimethylamino)propyl chloride

549-18-8

amitriptyline hydrochloride

Conditions
ConditionsYield
With hydrogenchloride; 1,1-Dibromoethane; magnesium 1) THF, reflux; 2) THF, reflux;; Yield given. Multistep reaction;
1210-35-1

10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-one

549-18-8

amitriptyline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: magnesium; I2 / tetrahydrofuran / Heating
1.2: 68 percent / tetrahydrofuran / 0 - 20 °C
2.1: 63 percent / aq. HCl / ethanol / Heating
View Scheme
Multi-step reaction with 3 steps
1: methanol / tetrahydrofuran; toluene / 20 °C / Flow reactor
2: ethanol / 0.01 h / 200 °C / 82508.3 Torr / Flow reactor
3: hydrogenchloride / isopropyl alcohol / 20 °C / Flow reactor
View Scheme
109-54-6

3-(Dimethylamino)propyl chloride

549-18-8

amitriptyline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: magnesium; I2 / tetrahydrofuran / Heating
1.2: 68 percent / tetrahydrofuran / 0 - 20 °C
2.1: 63 percent / aq. HCl / ethanol / Heating
View Scheme
50-48-6

Amitriptyline

549-18-8

amitriptyline hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In isopropyl alcohol at 20℃; Flow reactor;
3433-80-5

1-Bromo-2-bromomethyl-benzene

549-18-8

amitriptyline hydrochloride

Conditions
ConditionsYield
Multi-step reaction with 4 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
4: hydrogenchloride / isopropyl alcohol / 20 °C / Flow reactor
View Scheme
Multi-step reaction with 4 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
4: hydrogenchloride / isopropyl alcohol / 20 °C / Flow reactor
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

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
549-18-8

amitriptyline hydrochloride

107-05-1

3-chloroprop-1-ene

N-allyl-N-methyl-3-(2-tricyclo[9.4.0.03,8]pentadeca-1(11),3(8),4,6,12,14-hexaenylidene)propan-1-amine

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; Inert atmosphere;26%
549-18-8

amitriptyline hydrochloride

19660-95-8

5-(3-N,N-dimethylaminopropyl)-10,11-dihydro-5H-dibenzocycloheptene

Conditions
ConditionsYield
With perchloric acid; hydrogen; platinum(IV) oxide
1128-67-2

3-methyl-2-benzothiazolinone hydrazone

549-18-8

amitriptyline hydrochloride

2-[5-(3-dimethylamino-propylidene)-10,11-dihydro-5H-dibenzo[a,d]cyclohepten-2-ylazo]-3-methyl-benzothiazol-3-ium

Conditions
ConditionsYield
With hydrogenchloride; iron(III) chloride In water at 30℃; for 0.25h; Condensation;
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    CAS RN.: 549-18-8 EINECS: 208-964-6 Molecular Weight:

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Chemistry


Systematic Name: 3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)-N,N-dimethylpropan-1-amine hydrochloride (1:1)
Molecular Formula: C20H24ClN
Molecular Weight: 313.86 g/mol
EINECS: 208-964-6
Classification Code: Antidepressant; Drug / Therapeutic Agent; Human Data; Mutation data; Reproductive Effect
storage temp.: 2-8 °C
solubility: H2O: soluble
Flash Point: 174 °C
Enthalpy of Vaporization: 64.88 kJ/mol
Boiling Point: 398.2 °C at 760 mmHg
Melting Point: 196-197 °C
Vapour Pressure of Elavil hydrochloride (CAS NO.549-18-8): 1.5E-06 mmHg at 25 °C

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral 37mg/kg (37mg/kg)   Drug Development Research. Vol. 22, Pg. 385, 1991.
child LDLo oral 62500ug/kg (62.5mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
New England Journal of Medicine. Vol. 267, Pg. 1031, 1962.
child LDLo oral 62500ug/kg (62.5mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
American Journal of Diseases of Children. Vol. 106, Pg. 501, 1963.
child TDLo oral 4167ug/kg (4.167mg/kg) BEHAVIORAL: SLEEP

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
New England Journal of Medicine. Vol. 267, Pg. 1031, 1962.
child TDLo oral 58mg/kg (58mg/kg) BEHAVIORAL: COMA

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Southern Medical Journal. Vol. 82, Pg. 1588, 1989.
dog LD50 intramuscular > 23mg/kg (23mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 899, 1972.
dog LD50 intravenous > 27mg/kg (27mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 899, 1972.
dog LDLo oral 200mg/kg (200mg/kg)   Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 889, 1972.
guinea pig LDLo intravenous 52mg/kg (52mg/kg) CARDIAC: OTHER CHANGES Therapie. Vol. 20, Pg. 67, 1965.
human TDLo oral 200mg/kg (200mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

BEHAVIORAL: COMA
JAMA, Journal of the American Medical Association. Vol. 230, Pg. 1405, 1974.
man TDLo oral 714ug/kg/1D-I (0.714mg/kg) BEHAVIORAL: ALTERATION OF OPERANT CONDITIONING

BEHAVIORAL: CHANGES IN PSYCHOPHYSIOLOGICAL TESTS
Human Psychopharmacology. Vol. 7, Pg. 273, 1992.
man TDLo oral 14286ug/kg (14.286mg/kg) BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Lancet. Vol. 2, Pg. 543, 1963.
man TDLo oral 60mg/kg/3W-I (60mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ATAXIA

BEHAVIORAL: WITHDRAWAL
Journal of Clinical Psychiatry. Vol. 53, Pg. 160, 1992.
monkey LDLo intravenous 20300ug/kg (20.3mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Indian Journal of Experimental Biology. Vol. 22, Pg. 539, 1984.
mouse LD50 intraperitoneal 65mg/kg (65mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Journal of Drug Research. Vol. 16, Pg. 7, 1985.
mouse LD50 intravenous 21mg/kg (21mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 21, Pg. 808, 1971.
mouse LD50 oral 140mg/kg (140mg/kg)   Wiener Medizinische Wochenschrift. Vol. 111, Pg. 256, 1961.
mouse LD50 subcutaneous 80mg/kg (80mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 889, 1972.
rabbit LD50 intravenous 9900ug/kg (9.9mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 61, 1972.
rat LD50 intraperitoneal 67mg/kg (67mg/kg)   Drugs in Japan Vol. -, Pg. 49, 1990.
rat LD50 intravenous 14mg/kg (14mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 61, 1972.
rat LD50 oral 240mg/kg (240mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 889, 1972.
rat LD50 subcutaneous 385mg/kg (385mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: CYANOSIS
European Journal of Pharmacology. Vol. 32, Pg. 108, 1975.
women LDLo oral 19mg/kg (19mg/kg) BEHAVIORAL: COMA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Lancet. Vol. 2, Pg. 543, 1963.
women TDLo oral 10mg/kg (10mg/kg) BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" Canadian Medical Association Journal. Vol. 129, Pg. 1203, 1983.

Consensus Reports

Reported in EPA TSCA Inventory.

Safety Profile

Hazard Codes: ToxicT,FlammableF
Risk Statements: 23/24/25-36/37/38-42/43-63-39/23/24/25-11 
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R42/43:May cause sensitization by inhalation and skin contact. 
R63:Possible risk of harm to the unborn child. 
R39:Danger of very serious irreversible effects. 
R11:Highly flammable.
Safety Statements: 22-26-36/37/39-45-36/37-16 
S22:Do not breathe dust. 
S16:Keep away from sources of ignition. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36/37:Wear suitable protective clothing and gloves.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: HO9450000
HazardClass: 6.1(b)
PackingGroup: III
Poison by ingestion, intraperitoneal, intravenous, and subcutaneous routes. Human systemic effects by ingestion: convulsions, respiratory depression, changes in sleep, hallucinations, muscle contractions, somnolence, blood pressure decrease, coma, cyanosis, dyspnea, and ataxia. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. Used in the treatment of depression. When heated to decomposition it emits very toxic fumes of HCl and NOx.

Specification

  Elavil hydrochloride (CAS NO.549-18-8), its Synonyms are Amitriptyline hydrochloride ; 1-Propanamine, 3-(10,11-dihydro-5H-dibenzo(a,d)cyclohepten-5-ylidene)-N,N-dimethyl-, hydrochloride ; 10,11-Dihydro-N,N-dimethyl-5H-dibenzo(a,d)cycloheptene-delta(sup 5,gamma)-propylamine hydrochloride ; 5-(3-Dimethylaminopropylidene)dibenzo(a,d)(1,4)cycloheptadiene hydrochloride ; Amitrip ; Amitriptyline HCl ; 5H-Dibenzo(a,d)cycloheptene-delta5,gamma-propylamine, 10,11-dihydro-N,N-dimethyl-, hydrochloride (8CI) .