Synthetic Routes and Reaction Conditions: Amitriptyline can be synthesized through several methods. One common method involves the reaction of dibenzosuberone with dimethylamine in the presence of a reducing agent such as lithium aluminum hydride. The reaction proceeds through the formation of an intermediate, which is then cyclized to form amitriptyline .

Industrial Production Methods: In industrial settings, amitriptyline is typically produced through a multi-step synthesis process that ensures high yield and purity. The process involves the use of advanced techniques such as high-performance liquid chromatography (HPLC) for purification and quality control .

化学反応の分析

反応の種類： アミトリプチリンは、以下を含むさまざまな化学反応を起こします。

酸化： アミトリプチリンは酸化されてN-オキシド誘導体を形成することができます。

還元： アミトリプチリンの還元は、第二アミンを形成する可能性があります。

置換： アミトリプチリンは、特に窒素原子で求核置換反応を起こす可能性があります.

一般的な試薬と条件：

酸化： 一般的な酸化剤には、過酸化水素や過酸が含まれます。

還元： 水素化リチウムアルミニウムや水素化ホウ素ナトリウムなどの還元剤が一般的に使用されます。

置換： アルキルハライドやアシルクロリドなどの求核剤は、塩基性条件下で使用できます.

生成される主な生成物：

酸化： N-オキシド誘導体の形成。

還元： 第二アミンの形成。

置換： 置換アミトリプチリン誘導体の形成.

4. 科学研究への応用

アミトリプチリンは、幅広い科学研究への応用があります。

化学： 三環系抗うつ薬の研究におけるモデル化合物として使用されます。

生物学： 神経伝達物質系と受容体結合への影響について調査されています。

医学： うつ病、神経性疼痛、片頭痛の治療における治療効果について広く研究されています.

産業： 新しい医薬品製剤や薬物送達システムの開発に使用されています.

類似化合物との比較

Amitriptyline is often compared with other tricyclic antidepressants such as:

Nortriptyline: Similar in structure but has fewer side effects.

Desipramine: Known for its higher selectivity for norepinephrine reuptake inhibition.

Imipramine: Used for similar indications but has a different side effect profile.

Doxepin: Also used for depression and anxiety but has additional antihistaminic properties

Amitriptyline is unique due to its broad spectrum of action, affecting multiple neurotransmitter systems and receptors, which contributes to its efficacy in treating a variety of conditions .

特性

IUPAC Name	N,N-dimethyl-3-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylidene)propan-1-amine	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI	InChI=1S/C20H23N/c1-21(2)15-7-12-20-18-10-5-3-8-16(18)13-14-17-9-4-6-11-19(17)20/h3-6,8-12H,7,13-15H2,1-2H3	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

InChI Key	KRMDCWKBEZIMAB-UHFFFAOYSA-N	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Canonical SMILES	CN(C)CCC=C1C2=CC=CC=C2CCC3=CC=CC=C31	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Molecular Formula	C20H23N	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Related CAS	17086-03-2 (pamoate (2:1)), 30227-34-0 (maleate (1:1)), 549-18-8 (hydrochloride)	Source
Record name	Amitriptyline [INN:BAN]
Source	ChemIDplus
URL	https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000050486
Description	ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system.

DSSTOX Substance ID	DTXSID7022594	Source
Record name	Amitriptyline
Source	EPA DSSTox
URL	https://comptox.epa.gov/dashboard/DTXSID7022594
Description	DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.

Molecular Weight	277.4 g/mol	Source
Source	PubChem
URL	https://pubchem.ncbi.nlm.nih.gov
Description	Data deposited in or computed by PubChem

Physical Description	Solid	Source
Record name	Amitriptyline
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0014466
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation	HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Boiling Point	410.26°C (rough estimate)	Source
Record name	Amitriptyline
Source	DrugBank
URL	https://www.drugbank.ca/drugs/DB00321
Description	The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information.
Explanation	Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)

Solubility	freely soluble in water, In water, 9.71 mg/L at 24 °C, 4.50e-03 g/L	Source
Record name	Amitriptyline
Source	DrugBank
URL	https://www.drugbank.ca/drugs/DB00321
Description	The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information.
Explanation	Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)

Record name	AMITRIPTYLINE
Source	Hazardous Substances Data Bank (HSDB)
URL	https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3007
Description	The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel.

Record name	Amitriptyline
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0014466
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation	HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Mechanism of Action	The mechanism of action of this drug is not fully elucidated. It is suggested that amitriptyline inhibits the membrane pump mechanism responsible for the re-uptake of transmitter amines, such as norepinephrine and serotonin, thereby increasing their concentration at the synaptic clefts of the brain,. These amines are important in regulating mood. The monoamine hypothesis in depression, one of the oldest hypotheses, postulates that deficiencies of serotonin (5-HT) and/or norepinephrine (NE) neurotransmission in the brain lead to depressive effects. This drug counteracts these mechanisms, and this may be the mechanism of amitriptyline in improving depressive symptoms. Whether its analgesic effects are related to its mood-altering activities or attributable to a different, less obvious pharmacological action (or a combination of both) is unknown., Acute and chronic effects of the antidepressant drugs tranylcypromine, a monoamine oxidase inhibitor, and amitriptyline, a monoamine uptake inhibitor, were studied on beta-adrenergic receptor function in mouse astrocytes in primary cultures. In clinically relevant concentrations, acute administration of either antidepressant drug had a direct inhibitory effect on the binding of the beta-adrenergic ligand dihydroalprenolol and on the isoproterenol-induced accumulation of cyclic AMP. However, in the absence of isoproterenol, these drugs enhanced the formation of cyclic AMP in the astrocytes. Chronic exposure to amitriptyline or tranylcypromine led to a decrease in isoproterenol-induced accumulation of cyclic AMP, and the time course for the development of this phenomenon was similar to that reported for whole brain in vivo. These findings suggest that these antidepressant drugs act as a partial agonists at beta-adrenergic receptors on astrocytes, and that the down-regulation of beta-adrenergic activity that occurs in vivo after chronic administration of antidepressant drugs may, to a large extent, take place in astrocytes and may result from the partial beta-agonist nature of the drugs., Astrocytes play important roles in guiding the construction of the nervous system, controlling extracellular ions and neurotransmitters, and regulating CNS synaptogenesis. Egr-1 is a transcription factor involved in neuronal differentiation and astrocyte cell proliferation. In this study, we investigated whether the tricyclic antidepressant (TCA) amitriptyline induces Egr-1 expression in astrocytes using rat C6 glioma cells as a model. We found that amitriptyline increased the expression of Egr-1 in a dose- and time-dependent manner. The amitriptyline-induced Egr-1 expression was mediated through serum response elements (SREs) in the Egr-1 promoter. SREs were activated by the Ets-domain transcription factor Elk-1 through the ERK and JNK mitogen-activated protein (MAP) kinase pathways. The inhibition of the ERK and JNK MAP kinase signals attenuated amitriptyline-induced transactivation of Gal4-Elk-1 and Egr-1 promoter activity. Our findings suggest that the induction of Egr-1 expression in astrocytes may be required to attain the therapeutic effects of antidepressant drugs., Antidepressants such as serotonin-noradrenaline reuptake inhibitors (SNRIs) and tricyclic antidepressants (TCAs) are frequently used for the management of neuropathic pain. Noradrenaline (NA) and serotonin (5-HT) increase in the spinal cord by reuptake inhibition is considered to be main mechanism of the therapeutic effect of antidepressants in neuropathic pain. In the present study, we examined the analgesic effects of duloxetine (SNRI) and amitriptyline (TCA) in a rat model of neuropathic pain induced by spinal nerve ligation (SNL). Intraperitoneal administration of duloxetine and amitriptyline dose-dependently (3,10 and 30 mg/kg) suppressed hyperalgesia induced by SNL. In vivo microdialysis in the lumbar spinal dorsal horn revealed that NA and 5-HT concentrations increased after intraperitoneal administration of duloxetine and amitriptyline (10 mg/kg, respectively). We further determined NA and 5-HT contents in homogenized samples from the ipsilateral dorsal spinal cord after SNL. Although the NA content in SNL rats 2 weeks after ligation was higher than that in SNL rats 4 weeks after ligation, the analgesic efficacy of duloxetine and amitriptyline was similar between two groups. The present study suggests that NA/5-HT increase in the spinal cord is crucial in the antihyperalgesic effect of duloxetine and amitriptyline. The plastic change of the descending noradrenergic system does not obviously affect the analgesic efficacy of duloxetine and amitriptyline., Recent studies show that neuronal and glial plasticity are important for the therapeutic action of antidepressants. Here, we demonstrated that amitriptyline, a tricyclic antidepressant, significantly increased GDNF mRNA and GDNF release in C6 cells. Furthermore, different classes of antidepressants increased GDNF release, but non-antidepressant psychotropic drugs did not. The amitriptyline-induced GDNF release was completely inhibited by U0126, a mitogen-activated protein kinase (MAPK)-extracellular signal-regulated kinase (ERK) kinase (MEK) inhibitor, but was not inhibited by H-89, a protein kinase A inhibitor or calphostin C, a protein kinase C inhibitor. These results suggest that the amitriptyline-induced GDNF release may be regulated through a MEK/MAPK pathway. Next, we examined the effects of monoamines on GDNF release, because antidepressants are known to increase monoamines. 5-HT increased GDNF mRNA and GDNF release, but noradrenaline and dopamine did not. The 5-HT-induced GDNF release was partially, but significantly, blocked by ketanserin, a 5-HT2A receptor antagonist. The 5-HT-induced GDNF release was completely inhibited by U0126, but was not inhibited by H-89 or calphostin C. These results suggest that the 5-HT-induced GDNF release was mediated through a MEK/MAPK pathway and, at least, 5-HT2A receptors. GDNF, as well as other neurotrophic factors, may contribute to explain the therapeutic action of antidepressants and suggest a novel strategy of pharmacological intervention., For more Mechanism of Action (Complete) data for AMITRIPTYLINE (13 total), please visit the HSDB record page.	Source
Record name	Amitriptyline
Source	DrugBank
URL	https://www.drugbank.ca/drugs/DB00321
Description	The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information.
Explanation	Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)

Record name	AMITRIPTYLINE
Source	Hazardous Substances Data Bank (HSDB)
URL	https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3007
Description	The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel.

Color/Form	Crystals
CAS No.	50-48-6	Source
Record name	Amitriptyline
Source	CAS Common Chemistry
URL	https://commonchemistry.cas.org/detail?cas_rn=50-48-6
Description	CAS Common Chemistry is an open community resource for accessing chemical information. Nearly 500,000 chemical substances from CAS REGISTRY cover areas of community interest, including common and frequently regulated chemicals, and those relevant to high school and undergraduate chemistry classes. This chemical information, curated by our expert scientists, is provided in alignment with our mission as a division of the American Chemical Society.
Explanation	The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.

Record name	Amitriptyline [INN:BAN]
Source	ChemIDplus
URL	https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0000050486
Description	ChemIDplus is a free, web search system that provides access to the structure and nomenclature authority files used for the identification of chemical substances cited in National Library of Medicine (NLM) databases, including the TOXNET system.

Record name	Amitriptyline
Source	DrugBank
URL	https://www.drugbank.ca/drugs/DB00321
Description	The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information.
Explanation	Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)

Record name	Amitriptyline
Source	EPA DSSTox
URL	https://comptox.epa.gov/dashboard/DTXSID7022594
Description	DSSTox provides a high quality public chemistry resource for supporting improved predictive toxicology.

Record name	Amitriptyline
Source	European Chemicals Agency (ECHA)
URL	https://echa.europa.eu/substance-information/-/substanceinfo/100.000.038
Description	The European Chemicals Agency (ECHA) is an agency of the European Union which is the driving force among regulatory authorities in implementing the EU's groundbreaking chemicals legislation for the benefit of human health and the environment as well as for innovation and competitiveness.
Explanation	Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.

Record name	AMITRIPTYLINE
Source	FDA Global Substance Registration System (GSRS)
URL	https://gsrs.ncats.nih.gov/ginas/app/beta/substances/1806D8D52K
Description	The FDA Global Substance Registration System (GSRS) enables the efficient and accurate exchange of information on what substances are in regulated products. Instead of relying on names, which vary across regulatory domains, countries, and regions, the GSRS knowledge base makes it possible for substances to be defined by standardized, scientific descriptions.
Explanation	Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.

Record name	AMITRIPTYLINE
Source	Hazardous Substances Data Bank (HSDB)
URL	https://pubchem.ncbi.nlm.nih.gov/source/hsdb/3007
Description	The Hazardous Substances Data Bank (HSDB) is a toxicology database that focuses on the toxicology of potentially hazardous chemicals. It provides information on human exposure, industrial hygiene, emergency handling procedures, environmental fate, regulatory requirements, nanomaterials, and related areas. The information in HSDB has been assessed by a Scientific Review Panel.

Record name	Amitriptyline
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0014466
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation	HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Melting Point	196-197, 196 - 197 °C	Source
Record name	Amitriptyline
Source	DrugBank
URL	https://www.drugbank.ca/drugs/DB00321
Description	The DrugBank database is a unique bioinformatics and cheminformatics resource that combines detailed drug (i.e. chemical, pharmacological and pharmaceutical) data with comprehensive drug target (i.e. sequence, structure, and pathway) information.
Explanation	Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)

Record name	Amitriptyline
Source	Human Metabolome Database (HMDB)
URL	http://www.hmdb.ca/metabolites/HMDB0014466
Description	The Human Metabolome Database (HMDB) is a freely available electronic database containing detailed information about small molecule metabolites found in the human body.
Explanation	HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.

Synthesis routes and methods I

Procedure details

6-Carboxyfluorescein (1.00 g, 2.66 mmol) was dissolved in 8 mL DMF, 306 mg (2.66 mmol) of N-hydroxysuccinimide (HOSu) was added, 549 mg (2.66 mmol) of 1,3-dicyclohexylcarbodiimide (DCC) was added, and the reaction stirred for 17 hours, under N2, in the dark. The reaction was then vacuum filtered, filtrate combined with 784 mg (2.65 mmol) of 2-aminoimipramine (26c), 0.56 mL (4.0 mmol) of triethylamine, and 4.0 mL DMF, and reaction allowed to stir 4 days under N2, in the dark. Reaction solvents were removed in vacuo and residue purified on reverse phase C18 preparative (1 mm) TLC plates, eluting with H2O/THF/HOAc (40/60/0.4) followed by preparative HPLC on a Waters mbondapak C18 column (19 mm×150 mm), eluting with H2O/THF/HOAc (35/65/0.4) at a flow rate of 7.0 mL/minute to yield 410 mg (24%) of the desired tracer (27) as an orange powder; mass spec (FAB) (M+H)+ 654.

Name

6-Carboxyfluorescein

Quantity

1 g

Type

reactant

Reaction Step One

Name

DMF

Quantity

8 mL

Type

solvent

Reaction Step One

Name

N-hydroxysuccinimide

Quantity

306 mg

Type

reactant

Reaction Step Two

Name

1,3-dicyclohexylcarbodiimide

Quantity

549 mg

Type

reactant

Reaction Step Three

[Compound]

Name

( 26c )

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Four

Name

triethylamine

Quantity

0.56 mL

Type

reactant

Reaction Step Four

Name

DMF

Quantity

4 mL

Type

solvent

Reaction Step Four

Name

( 27 )

Details

Synthesis routes and methods II

Procedure details

0.750 gm amitriptyline hydrochloride USP, is wetted with 1.5 ml of ethoxy diglycol reagent, and stirred into 75 gm of the base cream prepared as per example 3 and triple milled. A cream-type preparation results which contains amitriptyline hydrochloride @ 10 mg/ml

Name

amitriptyline hydrochloride

Quantity

0.75 g

Type

reactant

Reaction Step One

Name

ethoxy diglycol

Quantity

1.5 mL

Type

reactant

Reaction Step Two

[Compound]

Name

base

Quantity

75 g

Type

reactant

Reaction Step Three

Name

amitriptyline hydrochloride

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Four

Name

amitriptyline

Details

Synthesis routes and methods III

Procedure details

1-Chloro-amitriptyline (196 mg) in 3 ml. absolute ethanol was added to an ethanolic solution of 1.1 eq. d-tartaric acid and warmed for 5-10 mins. The title compound was precipitated with ethyl ether as a white powder. After purity and identification checks, the overall yield from amitriptyline base was 32%.

Name

1-Chloro-amitriptyline

Quantity

196 mg

Type

reactant

Reaction Step One

Name

d-tartaric acid

Quantity

0 (± 1) mol

Type

reactant

Reaction Step Two

Name

ethanol

Quantity

0 (± 1) mol

Type

solvent

Reaction Step Two

Name

amitriptyline

Details

Retrosynthesis Analysis

AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.

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Strategy Settings

Precursor scoring	Relevance Heuristic
Min. plausibility	0.01
Model	Template_relevance
Template Set	Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis
Top-N result to add to graph	6

Feasible Synthetic Routes

Reactant of Route 1

Amitriptyline

Reactant of Route 2

Amitriptyline

Reactant of Route 3

Amitriptyline

Reactant of Route 4

Amitriptyline

Reactant of Route 5

Amitriptyline

Reactant of Route 6

Amitriptyline

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BenchChemで提示されるすべての記事および製品情報は、情報提供を目的としています。BenchChemで購入可能な製品は、生体外研究のために特別に設計されています。生体外研究は、ラテン語の "in glass" に由来し、生物体の外で行われる実験を指します。これらの製品は医薬品または薬として分類されておらず、FDAから任何の医療状態、病気、または疾患の予防、治療、または治癒のために承認されていません。これらの製品を人間または動物に体内に導入する形態は、法律により厳格に禁止されています。これらのガイドラインに従うことは、研究と実験において法的および倫理的な基準の遵守を確実にするために重要です。

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6. 類似の化合物との比較

科学的研究の応用

生化学分析

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4. 科学研究への応用

類似化合物との比較

特性

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Synthesis routes and methods III

Procedure details

Retrosynthesis Analysis

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Feasible Synthetic Routes

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