ChemicalBook > CAS DataBase List > Amitriptyline

Amitriptyline

Product Name
Amitriptyline
CAS No.
50-48-6
Chemical Name
Amitriptyline
Synonyms
Amitriptylin;amitriptilina;Amitryptiline;Amitryptyline;Elavil;5-(3-dimethylaminopropylidene)-10,11-dihyro-5h-dibenzo(a,d)cycloheptene;5-(3-Dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo(a,d)cycloheptatriene;n750;elani;mk230
CBNumber
CB1159271
Molecular Formula
C20H23N
Formula Weight
277.4
MOL File
50-48-6.mol
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Amitriptyline Property

Melting point:
196-197°C
Boiling point:
410.26°C (rough estimate)
Density 
0.9415 (rough estimate)
refractive index 
1.7500 (estimate)
storage temp. 
Store at -20°C
pka
9.4(at 25℃)
Water Solubility 
9.7 mg/mL
Stability:
Light Sensitive
CAS DataBase Reference
50-48-6(CAS DataBase Reference)
NIST Chemistry Reference
Amitriptyline(50-48-6)
EPA Substance Registry System
Amitriptyline (50-48-6)
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Safety

HazardClass 
IRRITANT
Hazardous Substances Data
50-48-6(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Danger
Hazard statements

H318Causes serious eye damage

H361Suspected of damaging fertility or the unborn child

H410Very toxic to aquatic life with long lasting effects

Precautionary statements

P201Obtain special instructions before use.

P202Do not handle until all safety precautions have been read and understood.

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P281Use personal protective equipment as required.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P308+P313IF exposed or concerned: Get medical advice/attention.

P310Immediately call a POISON CENTER or doctor/physician.

P391Collect spillage. Hazardous to the aquatic environment

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Usbiological
Product number
A1382-06A
Product name
Amitriptyline
Packaging
500ul
Price
$393
Updated
2021/12/16
Biorbyt Ltd
Product number
orb573389
Product name
Amitriptyline
Purity
>98%
Packaging
100mg
Price
$397.8
Updated
2021/12/16
American Custom Chemicals Corporation
Product number
API0001457
Product name
AMITRIPTYLINE
Purity
95.00%
Packaging
500MG
Price
$403.2
Updated
2021/12/16
Biorbyt Ltd
Product number
orb573389
Product name
Amitriptyline
Purity
>98%
Packaging
250mg
Price
$606.9
Updated
2021/12/16
DC Chemicals
Product number
DC20206
Product name
Amitriptyline；MK-230,N-750,Ro41575
Purity
>98%
Packaging
1g
Price
$600
Updated
2021/12/16
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Amitriptyline Chemical Properties,Usage,Production

Originator

Elavil HCl Merck Sharp and,Dohme,US,1961

Uses

Antidepressant.

Uses

Amitriptyline is used for anxious-depressive conditions. It is easier to tolerate than imipramine.

Definition

ChEBI: An organic tricyclic compound that is 10,11-dihydro-5H-dibenzo[a,d][7]annulene substituted by a 3-(dimethylamino)propylidene group at position 5.

Manufacturing Process

Phthalic anhydride is reacted with phenylacetic acid to form 3- benzylidenephthalide which is then hydrogenated to 2-phenethylbenzoic acid. Conversion to the acid chloride followed by intramolecular dehydrochlorination yields the ketone, 5H-dibenzo[a,d]cyclohepten-5-one. The ketone undergoes a Grignard reaction with 3-(dimethylamino)propyl chloride to give 5-(γ- dimethylaminopropylidene)-5H-dibenzo[a,d]cycloheptene.
Then, as described in US Patent 3,205,264, a solution of 5-(γ- dimethylaminopropylidene)-5H-dibenzo[a,d]cycloheptene (42 grams; 0.153 mol) in 105 ml of ethanol is hydrogenated over Raney nickel (1.5 grams) at 65°C under an initial hydrogen pressure of 450 lb. After 1 mol of hydrogen is absorbed (3.5 hours), the reaction mixture is filtered to remove the catalyst and is acidified with 80 ml of 2.5 N hydrochloric acid (0.2 mol). The acidic solution is concentrated to dryness under vacuum and is flushed three times with 100 ml of benzene to remove residual water. The solid residue then is dried under vacuum at 40°C to yield 44.9 grams (94% of theory) of the product, MP 187-189.5°C, equivalent weight 307, ultraviolet absorption A% 2380432. Recrystallization from isopropyl alcohol and ether affords the product in high purity.
In practice it is usually used as hydrochloride.

brand name

Elavil (AstraZeneca); Endep (Roche);Ami-anelun;Amilent;Amilit-ifi;Aminiurin;Amitimid;Amitriptol;Amyline;Amyzol;Annolytin;Apo-amitriptylline;Apo-pram;Deprelio;Deprestal;Diapatal;Elatrolet;Elavil plus;Emitrip;Enovil;Entrafon-210;Entrafon-2-10;Entrafon-2-25;Entrafon-a;Entrafon-forte;Etarfon;Etrafon-a;Etrafon-forte;Laroxal;Larozyl;Levate;Limbatarail;Limbatral;Limbitryl;Limitrol;Longopax;Loxaryl;Mareline;Meravil;Muaban d;Mutaban a/d/f;Nobrital;Novotriptyn;Novotryptin;Novo-tryptin;Parks-plus;Pms levazine;Prouvil;Saratem;Sarotena;Sedans;Sylvemid;Tensorelax;Teperin;Trepiline;Trepulin;Triptizol;Triptonal;Triptpane;Trivial-4-10.

Therapeutic Function

Antidepressant

World Health Organization (WHO)

Amitriptyline, a tricyclic antidepressant was introduced in 1961 for the management of endogenous depression and is listed in the 8th WHO Model List of Essential Drugs. Much of the adverse effects are caused by its antimuscarinic actions. These include dry mouth, cardiac arrhythmias, central nervous system disturbances, blood disorders and risk of suicide. The risk of suicide and dangers related to overdosage led the Norwegian Medicines Control Authority to put the higher strength formulation under prescribing restriction in 1992. The risk of death following overdosage is apparently higher for products containing tricyclic compounds as compared with nontricyclic products.

Biological Functions

Amitriptyline is a tertiary amine dibenzocycloheptadiene TCA with a propylidene side chain extending from the central carbocyclic ring. The diarylpropylideneamine moiety for amitriptyline makes it sensitive to photo-oxidation; therefore, its hydrochloride solutions should be protected from light to avoid ketone formation and precipitation.

Pharmacokinetics

Amitriptyline is rapidly absorbed from the GI tract and from parenteral sites.Amitriptyline and its active metabolite, nortriptyline, are distributed into breast milk. Amitriptyline is primarily (65%) metabolized by N-demethylation by CYP2D6 to nortriptyline and hydroxylation to its E-10-hydroxy metabolite. Nortriptyline is pharmacologically active as a secondary amine TCA. Amitriptyline shows approximately equal affinity for 5-HT and NE transporters.

Synthesis

Amitriptyline, 5-(3-dimethylaminopropyliden)-10,11-dihydrodibenzocycloheptene (7.1.4), differs from imipramine in that the nitrogen atom in the central part of the tricyclic system is replaced by a carbon, which is bound to a side chain by a double bond. Amitriptyline (7.1.4) is synthesized by interaction of 10,11-dihydro-N,N-dimethyl- 5H-dibenzo[a,d]cyclohepten-5-one with 3-dimethylaminopropylmagnesium bromide and the subsequent dehydration of the resulting tertiary alcohol (7.1.3) using hydrochloric acid [6–11].

An alternative way of synthesis of amitriptyline is by interaction of 10,11-dihydro-N,Ndimethyl-5H-dibenzo[a,d]-cyclohepten-5-one with cyclopropylmagnesium bromide, giving 10,11-dihydro-N,N-dimethyl-5H-dibenzo[a,d]-cyclohepten-5-cyclopropyl-5-ol (7.1.5). Reacting this with hydrogen bromide in acetic acid results in an opening of the cyclopropyl ring, which forms 5-(3-bromopropyliden)-10,11-dihydro-5H-dibenzo[a,d]-cycloheptene (7.1.6). Alkylating this with dimethylamine gives amitriptyline (7.1.4) [12,13].

Amitriptyline Preparation Products And Raw materials

Raw materials

Preparation Products

Amitriptyline hydrochloride
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View Lastest Price from Amitriptyline manufacturers

Wuhan Han Sheng New Material Technology Co.，Ltd
Product
Amitriptyline 50-48-6
Price
US $0.00-0.00/g
Min. Order
100g
Purity
99%
Supply Ability
20 tons
Release date
2023-07-19
Anhui Ruihan Technology Co., Ltd
Product
Amitriptyline 50-48-6
Price
US $30.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
1000t/year
Release date
2023-09-07
Guangzhou Biocar Biotechnology Co.,Ltd.
Product
Amitriptyline 50-48-6
Price
US $1.00/g
Min. Order
10g
Purity
99.5%
Supply Ability
1000kg
Release date
2022-01-10

50-48-6, AmitriptylineRelated Search:

Dimethyl sulfate Dimethyl carbonate Dacthal Dimethyl sulfoxide Propane N,N-Dimethylformamide Dimethyl fumarate Dimethyl ether ETHANE Dimethyl phthalate Amitriptyline Related Compound A (-)-2-[METHYLAMINO]-1-PHENYLPROPANE PIROHEPTINE Cotriptyline D/L-AMPHETAMINE HYDROCHLORIDE AMITRIPTYLINE HYDROCHLORIDE, PHARMA,AMITRIPTYLINE HCL,AMITRIPTYLINE HYDROCHLORIDE,sk-amitriptylin AMITRIPTYLINE HYDROCHLORIDE IMP C CYCLOHEPTENE

  • 5-(3-Dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo(a,d)cycloheptatriene
  • 5-(3-Dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo(a,d)cycloheptene
  • 5-(3-dimethylaminopropylidene)-10,11-dihyro-5h-dibenzo(a,d)cycloheptene
  • 5-(3'-Dimethylaminopropylidene)-dibenzo-(a,d)(1,4)-cycloheptadiene
  • 5-(3-Dimethylpropylidene)dibenzo(a,d)(1,4)cycloheptadiene
  • 5-(gamma-Dimethylaminopropylidene)-10,11-dihydro-5H-dibenzo(a,d)cycloheptene
  • 5-(gamma-Dimethylaminopropylidene)-5H-dibenzo(a,d)-10,11-dihydrocycloheptene
  • 5-(gamma-Dimethylaminopropylidene)-5H-Dibenzo[a,d][1,4]cycloheptadiene
  • 5-(gamma-Dimethylaminopropylidine)-5H-dibenzo(a,d)(1,4)cycloheptadiene
  • 3-(10,11-dihydro-5h-dibenzo(a,d)cyclohepten-5-ylidene)-n,n-dimethyl-1-propan
  • 5-(3’-dimethylaminopropylidene)-dibenzo-(a,d)(1,4)-cycloheptadiene
  • Damitriptyline
  • elani
  • Elanil
  • Elavil
  • Flavyl
  • Lantron
  • Laroxil
  • Laroxyl
  • Lentizol
  • mk230
  • MK-230
  • N 750
  • n750
  • Proheptadiene
  • MK-230, N-750, Ro41575
  • 5h-dibenzo(a,d)cycloheptene-delta(5,gamma)-propylamine,10,11-dihydro-n,n-dimet
  • 5H-Dibenzo[a,d]cycloheptene-delta5,gamma-propylamine, 10,11-dihydro-N,N-dimethyl-
  • Adepress
  • Adepril
  • amitriptilina
  • Amitriptylin
  • Amitryptiline
  • Amitryptyline
  • Amytriptiline
  • d)cyclopheptene-delta(sup5),gamma-propylamine,10,11-dihydro-n,n-5h-dibenzo(
  • Damilan
  • Damilen
  • AMITRIPTYLINE
  • AMITRYPTYLLINE NA
  • 10,11-Dihydro-5-(gamma-dimethylaminopropylidene)-5H-dibenzo(a,d)cycloheptene
  • 10,11-dihydro-n,n-dimethyl-5h-dibenzo(a,d)heptalene-delta(sup5),gamma-propyl
  • 10,11-Dihydro-N,N-dimethyl-5H-dibenzo(a,d)heptalene-delta<sup>5</sup>,gamma-propylamine
  • 1-Propanamine, 3-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-N,N-dimethyl-
  • redomex
  • Ro 4-1575
  • ro4-1575
  • sarotex
  • Seroten
  • Triptanol
  • Triptisol
  • Tryptanol
  • Tryptizol
  • Larxyl
  • 3-(10,11-Dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)-N,N-dimethyl-1-propanamine
  • 3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)-N,N-diMethylpropan-1-aMine
  • 3-(10,11-dihydro-5h-dibenzo[a,d]cyclohepten-5-ylidene)-n,n-dimethyl-1-propanamine
  • [3-(10,11-DIHYDRO-DIBENZO[A,D]CYCLOHEPTEN-5-YLIDENE)-PROPYL]-DIMETHYL-AMINE