Synonym
Amitriptyline HCl; Amitriptyline hydrochloride; Elavil; Amitriptylin; Tryptanol; Damilen; Triptanol
IUPAC/Chemical Name
3-(10,11-dihydro-5H-dibenzo[a,d][7]annulen-5-ylidene)-N,N-dimethylpropan-1-amine hydrochloride
InChi Key
KFYRPLNVJVHZGT-UHFFFAOYSA-N
InChi Code
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
SMILES Code
CN(C)CC/C=C1C2=CC=CC=C2CCC3=CC=CC=C\13.[H]Cl
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Amitriptyline hydrochloride is an inhibitor of serotonin reuptake transporter (SERT) and noradrenaline reuptake transporter (NET), with Kis of 3.45 nM and 13.3 nM for human SERT and NET, respectively.
In vivo activity:
After 1st day results show significant decrease of brain β-endorphin, which was present also in rat brains after 9th day of continuous Amitryptilin administration, compared to those of control group (Chart 2). We consider these changes as a consequence of continuous drug administration, despite constant variations in concentration, and rapid β-endorphin degradation. Results obtained by other authors, who were using different antidepressant drugs, speak in favour of β-endorphin value changes got in our investigation, previously shoved in our study with Trazodon.
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| DMSO |
54.9 |
174.75 |
|
| DMF |
25.0 |
79.65 |
|
| Ethanol |
44.0 |
140.19 |
|
| PBS (pH 7.2) |
0.5 |
1.59 |
|
| Water |
32.1 |
102.37 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
313.87
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Jadrić R, Hasić S, Kiseljaković E, Radovanović J, Ićindić-Nakas E, Winterhalter-Jadrić M. Effects of amitryptiline administration on rat sera and brain beta-endorphins. Bosn J Basic Med Sci. 2006 Nov;6(4):64-6. doi: 10.17305/bjbms.2006.3124. PMID: 17177653; PMCID: PMC5807973.
In vivo protocol:
1. Jadrić R, Hasić S, Kiseljaković E, Radovanović J, Ićindić-Nakas E, Winterhalter-Jadrić M. Effects of amitryptiline administration on rat sera and brain beta-endorphins. Bosn J Basic Med Sci. 2006 Nov;6(4):64-6. doi: 10.17305/bjbms.2006.3124. PMID: 17177653; PMCID: PMC5807973.
1: Aydin B, Hocaoglu N, Micili SC, Ergur BU, Kalkan S. Effects of 2-Hydroxypropyl-Beta-Cyclodextrin on Cardiovascular Signs of Amitriptyline Poisoning in a Rat Model. Cardiovasc Toxicol. 2015 Nov 30. [Epub ahead of print] PubMed PMID: 26621115.
2: Schmidt JJ, Bertram A, Kühn-Velten WN, Suhling H, Wiesner O, Schneider A, Kielstein JT. Treatment of amitriptyline intoxications by extended high cut-off dialysis. Clin Kidney J. 2015 Dec;8(6):796-9. doi: 10.1093/ckj/sfv094. Epub 2015 Sep 29. PubMed PMID: 26613042; PubMed Central PMCID: PMC4655799.
3: Abdulmajeed WI, Ibrahim RB, Ishola AO, Balogun WG, Cobham AE, Amin A. Amitriptyline and phenytoin prevents memory deficit in sciatic nerve ligation model of neuropathic pain. J Basic Clin Physiol Pharmacol. 2015 Nov 13. pii: /j/jbcpp.ahead-of-print/jbcpp-2014-0052/jbcpp-2014-0052.xml. doi: 10.1515/jbcpp-2014-0052. [Epub ahead of print] PubMed PMID: 26565548.
4: Taziki S, Sattari MR, Dastmalchi S, Eghbal MA. Cytoprotective Effects of Melatonin Against Amitriptyline-Induced Toxicity in Isolated Rat Hepatocytes. Adv Pharm Bull. 2015 Sep;5(3):329-34. doi: 10.15171/apb.2015.046. Epub 2015 Sep 19. PubMed PMID: 26504754; PubMed Central PMCID: PMC4616901.
5: Aonurm-Helm A, Anier K, Zharkovsky T, Castrén E, Rantamäki T, Stepanov V, Järv J, Zharkovsky A. NCAM-deficient mice show prominent abnormalities in serotonergic and BDNF systems in brain - Restoration by chronic amitriptyline. Eur Neuropsychopharmacol. 2015 Oct 21. pii: S0924-977X(15)00326-0. doi: 10.1016/j.euroneuro.2015.10.001. [Epub ahead of print] PubMed PMID: 26499173.
6: Mercadante S. Topical amitriptyline and ketamine for the treatment of neuropathic pain. Expert Rev Neurother. 2015 Nov;15(11):1249-53. doi: 10.1586/14737175.2015.1101347. Epub 2015 Oct 21. PubMed PMID: 26488799.
7: Damapong P, Kanchanakhan N, Eungpinichpong W, Putthapitak P, Damapong P. A Randomized Controlled Trial on the Effectiveness of Court-Type Traditional Thai Massage versus Amitriptyline in Patients with Chronic Tension-Type Headache. Evid Based Complement Alternat Med. 2015;2015:930175. doi: 10.1155/2015/930175. Epub 2015 Sep 15. PubMed PMID: 26472986; PubMed Central PMCID: PMC4587431.
8: Ratajczak-Enselme M, Grégoire N, Estebe JP, Dollo G, Chevanne F, Bec D, Ecoffey C, Couet W, Le Corre P. Population Pharmacokinetics of Amitriptyline After Intrathecal, Epidural, and Intravenous Administration in Sheep. Reg Anesth Pain Med. 2015 Nov-Dec;40(6):681-6. doi: 10.1097/AAP.0000000000000322. PubMed PMID: 26469370.
9: Zeng C, Zhu Z, Liu Q. HMGB1 is responsible for Amitriptyline-mediated cardiac protection from ischemic-reperfusion injury. Int J Cardiol. 2015 Sep 25. pii: S0167-5273(15)30379-X. doi: 10.1016/j.ijcard.2015.08.157. [Epub ahead of print] PubMed PMID: 26431816.
10: Rico-Villademoros F, Slim M, Calandre EP. Amitriptyline for the treatment of fibromyalgia: a comprehensive review. Expert Rev Neurother. 2015 Oct;15(10):1123-50. doi: 10.1586/14737175.2015.1091726. Epub 2015 Sep 22. PubMed PMID: 26395929.
(Last update: 4/21/2016).
