MedKoo Cat#: 341500 | Name: Tocainide hydrochloride
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Description:

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

Tocainide is a lidocaine analog, that does not have significant 1st pass metabolism. It is found in two enantiomers. The R isomer is 4x as potent as the S. Oral bioavailability is 0.9-1.0. In the blood tocainide is 10-20% protein bound. The Volume of distribution is 2.5-3.5 L/kg. 30-50% is excreted unchanged in the urine. The more active R-isomer is cleared faster in anephric patients or those with severe renal dysfunction. The main metabolite is the glucuronidated tocainide carbamic acid. The glucuronosyl transferase is apparently induced by rifampin. Weak inhibition of Cyp1A2 leads to a mild theophylline interaction. Tocainide was removed from market in 2003 due to adverse health effects in humans.

Chemical Structure

Tocainide hydrochloride
CAS#71395-14-7 (HCl)

Theoretical Analysis

MedKoo Cat#: 341500

Name: Tocainide hydrochloride

CAS#: 71395-14-7 (HCl)

Chemical Formula: C11H17ClN2O

Exact Mass: 0.0000

Molecular Weight: 228.72

Elemental Analysis: C, 57.77; H, 7.49; Cl, 15.50; N, 12.25; O, 7.00

Price and Availability

Size Price Availability Quantity
10mg USD 400.00 2 weeks
25mg USD 600.00 2 Weeks
50mg USD 950.00 2 Weeks
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Related CAS #
71395-14-7 (HCl) 41708-72-9 (free base) 53984-74-0 (R-isomer HCl) 53984-76-2 (S-isomer HCl)
Synonym
Tocainide hydrochloride; Alanyl-2,6-xylidide; Astra W 36095; W-36095; W36095; W 36095;
IUPAC/Chemical Name
2-Amino-N-(2,6-dimethylphenyl)propanamide hydrochloride
InChi Key
AMZACPWEJDQXGW-UHFFFAOYSA-N
InChi Code
InChI=1S/C11H16N2O.ClH/c1-7-5-4-6-8(2)10(7)13-11(14)9(3)12;/h4-6,9H,12H2,1-3H3,(H,13,14);1H
SMILES Code
CC(N)C(NC1=C(C)C=CC=C1C)=O.[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
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

Preparing Stock Solutions

The following data is based on the product molecular weight 228.72 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.

Recalculate based on batch purity %
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
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Epub 2014 Jan 10. PubMed PMID: 24472243. 7: Zhang J, Yang M, Zhou M, He L, Chen N, Zakrzewska JM. Non-antiepileptic drugs for trigeminal neuralgia. Cochrane Database Syst Rev. 2013 Dec 3;(12):CD004029. doi: 10.1002/14651858.CD004029.pub4. Review. PubMed PMID: 24297506. 8: De Luca A, De Bellis M, Corbo F, Franchini C, Muraglia M, Catalano A, Carocci A, Camerino DC. Searching for novel anti-myotonic agents: pharmacophore requirement for use-dependent block of skeletal muscle sodium channels by N-benzylated cyclic derivatives of tocainide. Neuromuscul Disord. 2012 Jan;22(1):56-65. doi: 10.1016/j.nmd.2011.07.001. Epub 2011 Jul 29. PubMed PMID: 21802953; PubMed Central PMCID: PMC3314985. 9: Martin WJ, Forouzanfar T. The efficacy of anticonvulsants on orofacial pain: a systematic review. Oral Surg Oral Med Oral Pathol Oral Radiol Endod. 2011 May;111(5):627-33. doi: 10.1016/j.tripleo.2011.01.033. Review. PubMed PMID: 21497736. 10: Yang M, Zhou M, He L, Chen N, Zakrzewska JM. Non-antiepileptic drugs for trigeminal neuralgia. Cochrane Database Syst Rev. 2011 Jan 19;(1):CD004029. doi: 10.1002/14651858.CD004029.pub3. Review. Update in: Cochrane Database Syst Rev. 2013;12:CD004029. PubMed PMID: 21249658. 11: Ghelardini C, Desaphy JF, Muraglia M, Corbo F, Matucci R, Dipalma A, Bertucci C, Pistolozzi M, Nesi M, Norcini M, Franchini C, Camerino DC. Effects of a new potent analog of tocainide on hNav1.7 sodium channels and in vivo neuropathic pain models. Neuroscience. 2010 Aug 25;169(2):863-73. doi: 10.1016/j.neuroscience.2010.05.019. Epub 2010 May 16. PubMed PMID: 20580661. 12: Pistolozzi M, Franchini C, Corbo F, Muraglia M, De Giorgi M, Felix G, Bertucci C. Tocainide analogues binding to human serum albumin: a HPLAC and circular dichroism study. J Pharm Biomed Anal. 2010 Oct 10;53(2):179-85. doi: 10.1016/j.jpba.2010.03.005. Epub 2010 Mar 7. PubMed PMID: 20359840. 13: Carrieri A, Muraglia M, Corbo F, Pacifico C. 2D- and 3D-QSAR of tocainide and mexiletine analogues acting as Na(v)1.4 channel blockers. Eur J Med Chem. 2009 Apr;44(4):1477-85. doi: 10.1016/j.ejmech.2008.10.005. Epub 2008 Oct 14. PubMed PMID: 19027197. 14: Choi HJ, Jin JS, Hyun MH. Liquid chromatographic direct resolution of tocainide and its analogs on a (3,3'-diphenyl-1,1'-binaphthyl)-20-crown-6-based chiral stationary phase containing residual silanol protecting n-octyl groups. Chirality. 2009 Jan;21(1):11-5. doi: 10.1002/chir.20582. PubMed PMID: 18506839. 15: Catalano A, Carocci A, Corbo F, Franchini C, Muraglia M, Scilimati A, De Bellis M, De Luca A, Camerino DC, Sinicropi MS, Tortorella V. Constrained analogues of tocainide as potent skeletal muscle sodium channel blockers towards the development of antimyotonic agents. Eur J Med Chem. 2008 Nov;43(11):2535-40. doi: 10.1016/j.ejmech.2008.01.023. Epub 2008 Jan 31. PubMed PMID: 18342401. 16: Erve JC. 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Robust randomised control trials needed for drug treatments for trigeminal neuralgia. Evid Based Dent. 2006;7(4):107. PubMed PMID: 17187047.