MedKoo Cat#: 318189 | Name: Mepivacaine Hydrochloride
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Description:

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

Mepivacaine Hydrochloride is a local anesthetic. It reversibly blocks inward current of transient Na+, as well as the steady-state K+ outward current. Mepivacaine Hydrochloride blocks tandem pore (TASK) and Kv1.5, potassium channels in model systems.

Chemical Structure

Mepivacaine Hydrochloride
Mepivacaine Hydrochloride
CAS#1722-62-9 (HCl)

Theoretical Analysis

MedKoo Cat#: 318189

Name: Mepivacaine Hydrochloride

CAS#: 1722-62-9 (HCl)

Chemical Formula: C15H23ClN2O

Exact Mass: 0.0000

Molecular Weight: 282.81

Elemental Analysis: C, 63.70; H, 8.20; Cl, 12.54; N, 9.91; O, 5.66

Price and Availability

Size Price Availability Quantity
1g USD 350.00 2 weeks
2g USD 600.00 2 weeks
5g USD 1,150.00 2 weeks
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Related CAS #
1722-62-9 (HCl) 96-88-8 (free base)
Synonym
Mepivacaine Hydrochloride; Mepivacaine HCL; Mepivastesin; Carbocaina; Polocaine; Scandicain;
IUPAC/Chemical Name
N-(2,6-dimethylphenyl)-1-methylpiperidine-2-carboxamide;hydrochloride
InChi Key
RETIMRUQNCDCQB-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H22N2O.ClH/c1-11-7-6-8-12(2)14(11)16-15(18)13-9-4-5-10-17(13)3;/h6-8,13H,4-5,9-10H2,1-3H3,(H,16,18);1H
SMILES Code
CC1=C(C(=CC=C1)C)NC(=O)C2CCCCN2C.Cl
Appearance
White to off-white crystalline 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
Biological target:
Mepivacaine hydrochloride binds to specific voltage-gated sodium ion channels in neuronal cell membranes, which inhibits both sodium influx and membrane depolarization.
In vitro activity:
The local anesthetics mepivacaine and S(-)-bupivacaine also blocked Na(v)1.8 and TTXs channels differentially. While mepivacaine displayed a preferential use-dependent block of Na(v)1.8, S(-)-bupivacaine displayed a preference for TTXs Na(+) channels. Reference: Eur J Pharmacol. 2010 Mar 25;630(1-3):19-28. https://pubmed.ncbi.nlm.nih.gov/20044988/
In vivo activity:
The efficacy of topical anesthetics was evaluated in a preclinical rodent model of painful peripheral neuropathy induced by epineural administration of the HIV envelope protein gp120 delivered using saturated oxidized cellulose implanted around the sciatic nerve. Equipotent concentrations of mepivacaine and lidocaine applied topically to the tail of mice significantly increased tail withdrawal latencies in the tail flick test, demonstrating that both local anesthetics attenuate responding to a brief noxious stimulus. Reference: J Pain Res. 2016 Jun 6;9:361-71. https://pubmed.ncbi.nlm.nih.gov/27350758/
Solvent mg/mL mM
Solubility
Ethanol 8.0 28.29
Water 78.5 277.57
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 282.81 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
Formulation protocol:
1. Mosqueira M, Aykut G, Fink RHA. Mepivacaine reduces calcium transients in isolated murine ventricular cardiomyocytes. BMC Anesthesiol. 2020 Jan 8;20(1):10. doi: 10.1186/s12871-019-0926-0. PMID: 31914932; PMCID: PMC6947945. 2. Leffler A, Reckzeh J, Nau C. Block of sensory neuronal Na+ channels by the secreolytic ambroxol is associated with an interaction with local anesthetic binding sites. Eur J Pharmacol. 2010 Mar 25;630(1-3):19-28. doi: 10.1016/j.ejphar.2009.12.027. Epub 2010 Jan 4. PMID: 20044988. 3. Sagen J, Castellanos DA, Hama AT. Antinociceptive effects of topical mepivacaine in a rat model of HIV-associated peripheral neuropathic pain. J Pain Res. 2016 Jun 6;9:361-71. doi: 10.2147/JPR.S104397. PMID: 27350758; PMCID: PMC4902250. 4. Satoh K, Chikuda M, Ohashi A, Kumagai M, Sato M, Joh S. The effect of mepivacaine on swine lingual, pulmonary and coronary arteries. BMC Anesthesiol. 2015 Jul 14;15:101. doi: 10.1186/s12871-015-0085-x. PMID: 26169676; PMCID: PMC4499916.
In vitro protocol:
1. Mosqueira M, Aykut G, Fink RHA. Mepivacaine reduces calcium transients in isolated murine ventricular cardiomyocytes. BMC Anesthesiol. 2020 Jan 8;20(1):10. doi: 10.1186/s12871-019-0926-0. PMID: 31914932; PMCID: PMC6947945. 2. Leffler A, Reckzeh J, Nau C. Block of sensory neuronal Na+ channels by the secreolytic ambroxol is associated with an interaction with local anesthetic binding sites. Eur J Pharmacol. 2010 Mar 25;630(1-3):19-28. doi: 10.1016/j.ejphar.2009.12.027. Epub 2010 Jan 4. PMID: 20044988.
In vivo protocol:
1. Sagen J, Castellanos DA, Hama AT. Antinociceptive effects of topical mepivacaine in a rat model of HIV-associated peripheral neuropathic pain. J Pain Res. 2016 Jun 6;9:361-71. doi: 10.2147/JPR.S104397. PMID: 27350758; PMCID: PMC4902250. 2. Satoh K, Chikuda M, Ohashi A, Kumagai M, Sato M, Joh S. The effect of mepivacaine on swine lingual, pulmonary and coronary arteries. BMC Anesthesiol. 2015 Jul 14;15:101. doi: 10.1186/s12871-015-0085-x. PMID: 26169676; PMCID: PMC4499916.
1: Claunch KM, Eggleston RB, Baxter GM. Effects of approach and injection volume on diffusion of mepivacaine hydrochloride during local analgesia of the deep branch of the lateral plantar nerve in horses. J Am Vet Med Assoc. 2014 Nov 15;245(10):1153-9. doi: 10.2460/javma.245.10.1153. PubMed PMID: 25356717. 2: Ueda T, Niiyama S, Amoh Y, Katsuoka K. Linear scleroderma after contusion and injection of mepivacaine hydrochloride. Dermatol Online J. 2010 May 15;16(5):11. PubMed PMID: 20492828. 3: Giannellini V, Bambagiotti-Alberti M, Bartolucci G, Bruni B, Coran SA, Costantino F, Di Vaira M. Solid-state study of mepivacaine hydrochloride. J Pharm Biomed Anal. 2005 Sep 15;39(3-4):444-54. PubMed PMID: 15950424. 4: Rinchuse DJ, Smudski JW. Effects of short-term and long-term administration of procaine hydrochloride and mepivacaine hydrochloride on hexobarbital-induced sleeping times in mice. J Dent Res. 1975 Sep-Oct;54(5):926-30. PubMed PMID: 1058876. 5: Daniel SS, Morishima HO. The estimation of mepivacaine hydrochloride in biological fluids. Anesthesiology. 1967 Sep-Oct;28(5):924-7. PubMed PMID: 6035022. 6: SHEFFIELD WE, KENNEDY JJ, DORNETTE WH. CLINICAL EXPERIENCES WITH MEPIVACAINE HYDROCHLORIDE. Anesth Analg. 1964 Mar-Apr;43:192-8. PubMed PMID: 14164941. 7: CALISE PJ. A clinical appraisal of the potency and toxicity of mepivacaine hydrochloride (Carbocaine). Anesth Analg. 1961 Sep-Oct;40:551-6. PubMed PMID: 13689966. 8: WEIL C, SANTANGELO C, WELHAM FS, YACKEL RF. Clinical evaluation of mepivacaine hydrochloride by a new method. J Am Dent Assoc. 1961 Jul;63:26-32. PubMed PMID: 13783827. 9: Kay AT, Bolt DM, Ishihara A, Rajala-Schultz PJ, Bertone AL. Anti-inflammatory and analgesic effects of intra-articular injection of triamcinolone acetonide, mepivacaine hydrochloride, or both on lipopolysaccharide-induced lameness in horses. Am J Vet Res. 2008 Dec;69(12):1646-54. doi: 10.2460/ajvr.69.12.1646. PubMed PMID: 19046013. 10: Ding S, Zhu YQ, Wu YN, Cao D. [Efficacy and safety of 3% mepivacaine hydrochloride injection for oral local anesthesia]. Shanghai Kou Qiang Yi Xue. 2008 Jun;17(3):328-31. Chinese. PubMed PMID: 18661082. 11: Bolt DM, Ishihara A, Weisbrode SE, Bertone AL. Effects of triamcinolone acetonide, sodium hyaluronate, amikacin sulfate, and mepivacaine hydrochloride, alone and in combination, on morphology and matrix composition of lipopolysaccharide-challenged and unchallenged equine articular cartilage explants. Am J Vet Res. 2008 Jul;69(7):861-7. doi: 10.2460/ajvr.69.7.861. PubMed PMID: 18593234. 12: Takahama H. A fixed drug eruption that developed cross-sensitivity among amide local anaesthetics, including mepivacaine hydrochloride, lidocaine hydrochloride and propitocaine hydrochloride. J Eur Acad Dermatol Venereol. 2008 Nov;22(11):1400-1. doi: 10.1111/j.1468-3083.2008.02662.x. Epub 2008 Mar 7. PubMed PMID: 18331309. 13: Adachi Y, Watanabe K, Uchihashi Y, Sato T. [Urinary retention as a transient neurologic symptom after accidental total spinal anesthesia with mepivacaine hydrochloride]. Masui. 1999 Sep;48(9):1009-10. Japanese. PubMed PMID: 10513178. 14: Banhawy MA, Rashed RM, Bowler K, Stacey MJ. The effect of a single injection of mepivacaine hydrochloride on spermatogenesis in the rat. J Reprod Fertil. 1977 Nov;51(2):477-9. PubMed PMID: 592302. 15: Moore DC, Bridenbaugh LD, Bagdi PA, Bridenbaugh PO. Accumulation of mepivacaine hydrochloride during caudal block. Anesthesiology. 1968 May-Jun;29(3):585-8. PubMed PMID: 5647507. 16: Baumstark RJ, Seldin R. Angioneurotic edema. Report of a case of the allergic type caused by sensitivity to mepivacaine hydrochloride. Oral Surg Oral Med Oral Pathol. 1967 Apr;23(4):433-7. PubMed PMID: 5227392. 17: Morishima HO, Daniel SS, Finster M, Poppers PJ, James LS. Transmission of mepivacaine hydrochloride (carbocaine) across the human placenta. Anesthesiology. 1966 Mar-Apr;27(2):147-54. PubMed PMID: 5948319. 18: SADOVE MS, SANCHEZ JD. A clinical appraisal of mepivacaine hydrochloride (Carbocaine) in spinal anesthesia. J Int Coll Surg. 1963 Jan;39:45-54. PubMed PMID: 13975981. 19: SADOVE MS, VERNINO D, LOCK F, KOLODNY S. An evaluation of mepivacaine hydrochloride. J Oral Surg Anesth Hosp Dent Serv. 1962 Sep;20:399-404. PubMed PMID: 14495929. 20: AUERBACH ME, HEFFERREN JJ, KOEHLER HM, PRATT EL. Qualitative and quantitative tests for mepivacaine hydrochloride. J Pharm Sci. 1962 May;51:491-3. PubMed PMID: 13863212.