Amitriptyline HCl | CAS#50-48-6 | 549-18-8

Amitriptyline HCl
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 317182

CAS#: 549-18-8 (HCl)

Description: Amitriptyline, sold under the brand name Elavil among others, is a medication used to treat a number of mental illnesses. This including major depressive disorder and anxiety disorder, and less commonly attention deficit hyperactivity disorder and bipolar disorder. Other uses include prevention of migraines, treatment of neuropathic pain such as fibromyalgia and postherpetic neuralgia, and less commonly insomnia. It is taken by mouth. Common side effects include a dry mouth, trouble seeing, low blood pressure on standing, sleepiness, and constipation.

Chemical Structure

Amitriptyline HCl

CAS# 549-18-8 (HCl)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 317182
Name: Amitriptyline HCl
CAS#: 549-18-8 (HCl)
Chemical Formula: C20H24ClN
Exact Mass: 277.18
Molecular Weight: 313.869
Elemental Analysis: C, 76.54; H, 7.71; Cl, 11.29; N, 4.46

Price and Availability

Size	Price	Availability	Quantity
1g	USD 90
2g	USD 150
5g	USD 250
10g	USD 450
25g	USD 650
50g	USD 950
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 549-18-8 (HCl) 50-48-6 (free base)

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

Appearance: Solid powder

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

More Info:

Product Data:

Product Data

Instruction:

View handling instruction

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 vitro activity:	TBD
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.

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
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

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 vitro protocol:	TBD
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.

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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).

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