Amitriptyline Hydrochloride - ≥98% , Norepinephrine transporter inhibitor, CAS No.549-18-8, Norepinephrine transporter inhibitor

CAS: 549-18-8 Cat. No.: A129730 Molecular Weight: 313.86 EC Number: 208-964-6

GRADE & PURITY ≥98%

Synonyms

5H-Dibenzo(a,d)cycloheptene-delta5,gamma-propylamine, 10,11-dihydro-N,N-dimethyl-, hydrochloride | AMITRIPTYLINE HYDROCHLORIDE [USP MONOGRAPH] | Amyline | Novoprotect | SR-01000003046 | Tryptizol retard | AMITRIPTYLINE HYDROCHLORIDE (EP IMPURITY) | Larozy

Storage

Store at 2-8°C,Protected from light

Shipped In

Wet ice

Overview

Amitriptyline inhibits serotonin receptor, norepinephrine receptor, 5-HT4, 5-HT2 and sigma 1 receptor with IC50 of 3.45 nM, 13.3 nM, 7.31 nM, 235 nM and 287 nM, respectively.
Amitriptyline hydrochloride is a tricyclic antidepressant drug. Amitriptyline hydrochloride inhibits the norepinephrine and serotonin transporters but has a high affinity for α1-adrenergic, serotonin and muscarinic acetylcholine receptors.

Specifications

Synonyms

5H-Dibenzo(a, d)cycloheptene-delta5, gamma-propylamine, 10, 11-dihydro-N, N-dimethyl-, hydrochloride | AMITRIPTYLINE HYDROCHLORIDE [USP MONOGRAPH] | Amyline | Novoprotect | SR-01000003046 | Tryptizol retard | AMITRIPTYLINE HYDROCHLORIDE (EP IMPURITY) | Larozy

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Tricyclic antidepressant; inhibits the norepinephrine and serotonin transporters with Kis of 100 nM and 14.7 nM, respectively; high in vitro affinity for α1-adrenoceptors, serotonin and muscarinic acetylcholine receptors.Serotonin and noradrenalin uptake

Storage

Store at 2-8°C, Protected from light

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Mechanism of action

Norepinephrine transporter inhibitor

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 488181249
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488181249
• Canonical Smiles: CN(C)CCC=C1C2=CC=CC=C2CCC3=CC=CC=C31.Cl
• 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;hydrochloride
• InChIKey: KFYRPLNVJVHZGT-UHFFFAOYSA-N
• INCHI: 1S/C20H23N.ClH/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;1H
• Isomeric SMILES: CN(C)CCC=C1C2=CC=CC=C2CCC3=CC=CC=C31.Cl
• WGK Germany: 3
• RTECS: HO9450000
• Alternate CAS: 50-48-6
• Molecular Weight: 313.86
• Reaxy-Rn: 4164595
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=4164595&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Dibenzocycloheptenes

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Dibenzocycloheptenes
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Dibenzocycloheptenes
• Alternative Parents: Trialkylamines Organopnictogen compounds Hydrochlorides Hydrocarbon derivatives
• Molecular Framework: Aromatic homopolycyclic compounds
• Substituents: Dibenzocycloheptene - Tertiary aliphatic amine - Tertiary amine - Organic nitrogen compound - Organopnictogen compound - Hydrocarbon derivative - Hydrochloride - Organonitrogen compound - Amine - Aromatic homopolycyclic compound
• Description: This compound belongs to the class of organic compounds known as dibenzocycloheptenes. These are compounds containing a dibenzocycloheptene moiety, which consists of two benzene rings connected by a cycloheptene ring.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

Discover Target: ESR1

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NR3C1 Tclin Glucocorticoid receptor (14987 Activities)

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SLC6A2 Tclin Norepinephrine transporter (10102 Activities)

Discover Target: SLC6A2

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PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

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KCNH2 Tclin HERG (29587 Activities)

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THRB Tclin Thyroid hormone receptor beta-1 (7926 Activities)

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RXRA Tclin Retinoid X receptor alpha (3637 Activities)

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TRPV1 Tclin Vanilloid receptor (8273 Activities)

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ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

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NR1H4 Tclin Bile acid receptor FXR (6228 Activities)

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NFKB1 Tclin Nuclear factor NF-kappa-B p105 subunit (1459 Activities)

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GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)

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CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

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TP53 Tchem Cellular tumor antigen p53 (48468 Activities)

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ATM Tchem Serine-protein kinase ATM (4198 Activities)

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HEK293 (82097 Activities)

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HepG2 (196354 Activities)

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Lymphoblastoid cell (5959 Activities)

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GNAS Tbio Guanine nucleotide-binding protein G(s), subunit alpha (103405 Activities)

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APEX1 Tchem DNA-(apurinic or apyrimidinic site) lyase (38016 Activities)

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EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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KDM4E Tchem Lysine-specific demethylase 4D-like (40243 Activities)

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LMNA Tbio Prelamin-A/C (36751 Activities)

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SMAD3 Tchem Mothers against decapentaplegic homolog 3 (68039 Activities)

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GMNN Tbio Geminin (128009 Activities)

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PMP22 Tbio Peripheral myelin protein 22 (699 Activities)

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MBNL1 Tbio Muscleblind-like protein 1 (34431 Activities)

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SLCO1B1 Tchem Solute carrier organic anion transporter family member 1B1 (2672 Activities)

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MPHOSPH8 Tbio M-phase phosphoprotein 8 (656 Activities)

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SLCO1B3 Tchem Solute carrier organic anion transporter family member 1B3 (2517 Activities)

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ATXN2 Tbio Ataxin-2 (54410 Activities)

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IDH1 Tclin Isocitrate dehydrogenase [NADP] cytoplasmic (40980 Activities)

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MEN1 Tchem Menin/Histone-lysine N-methyltransferase MLL (48157 Activities)

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Associated Targets(non-human)

Ppard Peroxisome proliferator-activated receptor delta (358 Activities)

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Pseudomonas aeruginosa (123386 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Plasmodium falciparum (966862 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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Mus musculus (284745 Activities)

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lef Anthrax lethal factor (7585 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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TGR Thioredoxin glutathione reductase (28579 Activities)

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Mapt Microtubule-associated protein tau (6 Activities)

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

Discover Target: Nfe2l2

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Rorc Nuclear receptor ROR-gamma (89407 Activities)

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fba Putative fructose-1,6-bisphosphate aldolase (15559 Activities)

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Impa1 Inositol monophosphatase 1 (16203 Activities)

Discover Target: Impa1

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ffp 4'-phosphopantetheinyl transferase ffp (24982 Activities)

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nfo Endonuclease 4 (425 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in Chloroform
• Sensitivity: Light sensitive；Moisture sensitive
• Melt Point(°C): 195 °C
• Molecular Weight: 313.900 g/mol
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 3
• Exact Mass: 313.16 Da
• Monoisotopic Mass: 313.16 Da
• Topological Polar Surface Area: 3.200 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 331.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3

References

1. Cong Lu, Zhen Wei, Yongquan Wang, Shuying Li, Litao Tong, Xinmin Liu, Bei Fan, Fengzhong Wang.  (2022)  Soy isoflavones alleviate lipopolysaccharide-induced depressive-like behavior by suppressing neuroinflammation, mediating tryptophan metabolism and promoting synaptic plasticity.  Food & Function,  13  (18): (9513-9522).  [PMID:35993820] [10.1039/D2FO01437H]

2. Cong Lu, Rongjing Gao, Yingyu Zhang, Ning Jiang, Ying Chen, Jing Sun, Qiong Wang, Bei Fan, Xinmin Liu, Fengzhong Wang.  (2021)  S-equol, a metabolite of dietary soy isoflavones, alleviates lipopolysaccharide-induced depressive-like behavior in mice by inhibiting neuroinflammation and enhancing synaptic plasticity.  Food & Function,  12  (13): (5770-5778).  [PMID:34038497] [10.1039/D1FO00547B]

3. Libin Wan, Bin Lin, Ruiqin Zhu, Chuixiu Huang, Stig Pedersen-Bjergaard, Xiantao Shen.  (2019)  Liquid-Phase Microextraction or Electromembrane Extraction?.  ANALYTICAL CHEMISTRY,      [PMID:31141346] [10.1021/acs.analchem.9b00946]

4. Dan Liu, Ting Qiao, Haiyan Liu, Xiaoling Wang, Zhi-guo Shi.  (2017)  A simple approach to prepare a sulfone-embedded stationary phase for HPLC.  JOURNAL OF SEPARATION SCIENCE,  41  (4): (877-885).  [PMID:29205869] [10.1002/jssc.201700751]

5. Qianqian Shang, Yangyang Liu, Menghan Hou, Zhuangzhuang Dong, Stig Pedersen-Bjergaard, Chuixiu Huang, Xiantao Shen.  (2025)  Automated Formation of Supported Liquid Membranes by Molecular Self-Assembly: A Step Forward for Liquid-Phase Microextraction.  ANALYTICAL CHEMISTRY,      [PMID:41166073] [10.1021/acs.analchem.5c05134]