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| CAS No.: | 549-18-8 |
|---|---|
| Name: | Amitriptyline hydrochloride |
| Article Data: | 3 |
| Molecular Structure: | |
|
|
|
| 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: |
 T,  F
|
| 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 |
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- 894852-01-87-BROMO-2,2-DIMETHYL-2H-PYRIDO[3,2-B][1,4]OXAZIN-3(4H)-ONE
- 1159-03-1
5-(3-dimethylaminopropyl)-10,11-dihydrodibenzo[a,d]cyclohepten-5-ol
- 549-18-8
amitriptyline hydrochloride
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With hydrogenchloride; 1,1-Dibromoethane; magnesium 1) THF, reflux; 2) THF, reflux;; Yield given. Multistep reaction; |
| Conditions | Yield |
|---|---|
| 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 |
| Conditions | Yield |
|---|---|
| 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 |
| Conditions | Yield |
|---|---|
| With hydrogenchloride In isopropyl alcohol at 20℃; Flow reactor; |
| Conditions | Yield |
|---|---|
| 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 | 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 |
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With perchloric acid; hydrogen; platinum(IV) oxide |
| Conditions | Yield |
|---|---|
| With hydrogenchloride; iron(III) chloride In water at 30℃; for 0.25h; Condensation; |
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Chemistry
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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: 
T,
F
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) .