Prilocaine Hydrochloride | CAS#1786-81-8 | CAS#721-50-6 | Dental anesthetic

MedKoo Cat#: 318567 | Name: Prilocaine Hydrochloride

Featured

Description:

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

Priolocaine Hydrochloride is used as local nerve blocker and for spinal anesthesia. It is a local anesthetic of the amino amide type. Its pharmacological properties are similar to those of lidocaine. Prilocaine Hydrochloride is used as a local anesthetic across many dental procedures, with additional applications as a potential radioprotector.

Chemical Structure

Prilocaine Hydrochloride

CAS#1786-81-8 (HCl)

Theoretical Analysis

MedKoo Cat#: 318567

Name: Prilocaine Hydrochloride

CAS#: 1786-81-8 (HCl)

Chemical Formula: C13H21ClN2O

Exact Mass: 0.0000

Molecular Weight: 256.77

Elemental Analysis: C, 60.81; H, 8.24; Cl, 13.81; N, 10.91; O, 6.23

Price and Availability

Size	Price	Availability	Quantity
500mg	USD 150.00
1g	USD 250.00
2g	USD 450.00
5g	USD 650.00
10g	USD 1,050.00

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

1786-81-8 (HCl) 721-50-6 (free)

Synonym

Prilocaine Hydrochloride, Prilocaine HCl, Propitocaine hydrochloride, Xylonest, Prilocaine chloride, Xylonest, Citanest Octapressin

IUPAC/Chemical Name

N-(2-methylphenyl)-2-(propylamino)propanamide;hydrochloride

InChi Key

BJPJNTKRKALCPP-UHFFFAOYSA-N

InChi Code

InChI=1S/C13H20N2O.ClH/c1-4-9-14-11(3)13(16)15-12-8-6-5-7-10(12)2;/h5-8,11,14H,4,9H2,1-3H3,(H,15,16);1H

SMILES Code

CCCNC(C)C(=O)NC1=CC=CC=C1C.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

Product Data

Instruction

View handling instruction

Biological target:

Prilocaine hydrochloride, an amino amide, is a Na, K-ATPase inhibitor.

In vitro activity:

Prilocaine induced cell death in Saos-2 cells in a dose- and time-dependent manner up to the concentration of 10 mM. Marked nuclear condensation and fragmentation of chromatin were observed in the prilocaine-treated cells. DNA ladder formation also was induced by prilocaine treatment. Prilocaine-induced DNA ladder formation was dose-dependent with maximal effect at a concentration of 5 mM and was time-dependent from 12 to 48 hr. DNA ladder formation was also induced by prilocaine treatment in human osteoblastic MG63 cells and mouse osteoblastic MC3T3-E1 cells. Reference: Can J Anaesth. 1999 May;46(5 Pt 1):476-82. https://pubmed.ncbi.nlm.nih.gov/10349929/

In vivo activity:

Prilocaine, at a concentration of 20 µM, protected zebrafish from radiation induced (20 Gy) pericardial edema (PE), microphthalmia and rendered 60 % survival advantage over radiation exposed controls. Prilocaine, in a dose-dependent manner, scavenged, radiation-induced hydroxyl radicals and maximally (43 %) at the highest concentration (1 mM) tried in this study. However, prilocaine exerted a mild superoxide anion scavenging potential (around 5 %) at all the concentrations used within this study. Prilocaine, at 20 µM concentration, significantly increased erythropoiesis, a marker for HSC function, in caudal hematopoietic tissue (CHT) in wild type and anemic zebrafish embryos (1.48 and 0.85 folds respectively) when compared to untreated (1) and phenylhydrazine (PHZ) (0.41 fold) treated control groups respectively. Reference: Tokai J Exp Clin Med. 2015 Mar 20;40(1):8-15. https://pubmed.ncbi.nlm.nih.gov/25843444/

	Solvent	mg/mL	mM
Solubility
	DMF	20.0	77.89
	DMSO	35.5	138.25
	Ethanol	20.0	77.89
	PBS (pH 7.2)	10.0	38.94

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 256.77 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. Nakamura K, Kido H, Morimoto Y, Morimoto H, Kobayashi S, Morikawa M, Haneji T. Prilocaine induces apoptosis in osteoblastic cells. Can J Anaesth. 1999 May;46(5 Pt 1):476-82. doi: 10.1007/BF03012949. PMID: 10349929. 2. Dimri M, Joshi J, Shrivastava N, Ghosh S, Chakraborti R, Indracanti PK. Prilocaine hydrochloride protects zebrafish from lethal effects of ionizing radiation: role of hematopoietic cell expansion. Tokai J Exp Clin Med. 2015 Mar 20;40(1):8-15. PMID: 25843444.

In vitro protocol:

In vivo protocol:

1. Dimri M, Joshi J, Shrivastava N, Ghosh S, Chakraborti R, Indracanti PK. Prilocaine hydrochloride protects zebrafish from lethal effects of ionizing radiation: role of hematopoietic cell expansion. Tokai J Exp Clin Med. 2015 Mar 20;40(1):8-15. PMID: 25843444.

1: Yıldız ÖÖ, İnan K, Ağababaoğlu İ, Çınar E. Local treatment of pain in Tietze syndrome: A single-center experience. Turk Gogus Kalp Damar Cerrahisi Derg. 2021 Apr 26;29(2):239-247. doi: 10.5606/tgkdc.dergisi.2021.21120. PMID: 34104518; PMCID: PMC8167461. 2: Pilger D, Maier AK, Bertelmann E, Joussen A, Torun N. Use of topical anaesthesia and peribulbar anaesthesia in Descemets membrane endothelial keratoplasty. Eur J Ophthalmol. 2021 May;31(3):1431-1436. doi: 10.1177/1120672120950935. Epub 2020 Aug 27. PMID: 32854539. 3: Kubota K, Kyosaka Y, Ueda K, Minakuchi S. Increase in pulse pressure on administration of a dental local anesthetic solution, prilocaine hydrochloride with felypressin in male diabetic patients with coronary heart disease. Clin Oral Investig. 2020 Jan;24(1):239-246. doi: 10.1007/s00784-019-02924-x. Epub 2019 May 12. PMID: 31079247. 4: Bragagni M, Gil-Alegre ME, Mura P, Cirri M, Ghelardini C, Di Cesare Mannelli L. Improving the therapeutic efficacy of prilocaine by PLGA microparticles: Preparation, characterization and in vivo evaluation. Int J Pharm. 2018 Aug 25;547(1-2):24-30. doi: 10.1016/j.ijpharm.2018.05.054. Epub 2018 May 23. PMID: 29800738. 5: Khongkhunthian S, Sastraruji T, Klayraung S, Okonogi S. Efficacy of anesthetic rice nanogel on pain reduction in human oral cavity. Drug Discov Ther. 2018;12(1):31-36. doi: 10.5582/ddt.2018.01003. PMID: 29553081. 6: Khongkhunthian S, Supanchart C, Yotsawimonwat S, Okonogi S. In vitro oral epithelium cytotoxicity and in vivo inflammatory inducing effects of anesthetic rice gel. Drug Discov Ther. 2017;11(6):323-328. doi: 10.5582/ddt.2017.01066. PMID: 29332890. 7: do Couto RO, Cubayachi C, Calefi PL, Lopez RFV, Pedrazzi V, De Gaitani CM, de Freitas O. Combining amino amide salts in mucoadhesive films enhances needle- free buccal anesthesia in adults. J Control Release. 2017 Nov 28;266:205-215. doi: 10.1016/j.jconrel.2017.09.039. Epub 2017 Sep 30. PMID: 28974451. 8: Silva-Santisteban A, Steinke N, Johnston AJ, Ruiz GN, Carlos Pardo L, McLain SE. On the structure of prilocaine in aqueous and amphiphilic solutions. Phys Chem Chem Phys. 2017 May 24;19(20):12665-12673. doi: 10.1039/c7cp01723e. PMID: 28474037. 9: Manassero A, Fanelli A. Prilocaine hydrochloride 2% hyperbaric solution for intrathecal injection: a clinical review. Local Reg Anesth. 2017 Mar 31;10:15-24. doi: 10.2147/LRA.S112756. PMID: 28408851; PMCID: PMC5383067. 10: Cubayachi C, Couto RO, de Gaitani CM, Pedrazzi V, Freitas Od, Lopez RF. Needle-free buccal anesthesia using iontophoresis and amino amide salts combined in a mucoadhesive formulation. Colloids Surf B Biointerfaces. 2015 Dec 1;136:1193-201. doi: 10.1016/j.colsurfb.2015.11.005. Epub 2015 Nov 10. PMID: 26590633. 11: Couto RO, Cubayachi C, Lopez RF, de Gaitani CM, Pedrazzi V, de Freitas O. A simple and high-resolution HPLC-PDA method for simultaneous quantification of local anesthetics in in vitro buccal permeation enhancement studies. Biomed Chromatogr. 2016 Jun;30(6):857-66. doi: 10.1002/bmc.3619. Epub 2015 Nov 17. PMID: 26379211. 12: Elkin I, Weight AK, Klibanov AM. Markedly lowering the viscosity of aqueous solutions of DNA by additives. Int J Pharm. 2015 Oct 15;494(1):66-72. doi: 10.1016/j.ijpharm.2015.08.019. Epub 2015 Aug 7. PMID: 26260229. 13: Dimri M, Joshi J, Shrivastava N, Ghosh S, Chakraborti R, Indracanti PK. Prilocaine hydrochloride protects zebrafish from lethal effects of ionizing radiation: role of hematopoietic cell expansion. Tokai J Exp Clin Med. 2015 Mar 20;40(1):8-15. PMID: 25843444. 14: Arik HO, Kose O, Guler F, Deniz G, Egerci OF, Ucar M. Injection of autologous blood versus corticosteroid for lateral epicondylitis: a randomised controlled study. J Orthop Surg (Hong Kong). 2014 Dec;22(3):333-7. doi: 10.1177/230949901402200313. PMID: 25550013. 15: Podolak-Machowska A, Kostecka J, Librowski T, Santocki M, Bigaj J, Plytycz B. Effects of anesthetic compounds on responses of earthworms to electrostimulation. Folia Biol (Krakow). 2014;62(2):155-62. doi: 10.3409/fb62_2.155. PMID: 25134346. 16: Berlit S, Tuschy B, Brade J, Mayer J, Kehl S, Sütterlin M. Effectiveness of nitrous oxide for postpartum perineal repair: a randomised controlled trial. Eur J Obstet Gynecol Reprod Biol. 2013 Oct;170(2):329-32. doi: 10.1016/j.ejogrb.2013.06.025. Epub 2013 Jul 24. PMID: 23891062. 17: Bjelanović Z, Leković I, Drasković M, Tomić A, Veljović M, Stamenković D, Stanković N. Ambulatory phlebectomy under tumescent local anesthesia in a kidney-transplant patient. Vojnosanit Pregl. 2013 Apr;70(4):417-9. doi: 10.2298/vsp1304417b. PMID: 23700949. 18: Ilko D, Holzgrabe U. Influence of the capillary diameter on the separation efficiency and sensitivity: a systematic approach. Electrophoresis. 2012 Jun;33(11):1494-8. doi: 10.1002/elps.201100575. PMID: 22736349. 19: Inagawa M, Ichinohe T, Kaneko Y. Felypressin, but not epinephrine, reduces myocardial oxygen tension after an injection of dental local anesthetic solution at routine doses. J Oral Maxillofac Surg. 2010 May;68(5):1013-7. doi: 10.1016/j.joms.2009.07.080. Epub 2009 Dec 23. PMID: 20031290. 20: Gupta H, Singh RM, Singh GN, Kaushik D, Sharma A. pH-Induced In Situ Gel for Periodontal Anesthesia. Indian J Pharm Sci. 2008 Nov;70(6):776-8. doi: 10.4103/0250-474X.49120. PMID: 21369439; PMCID: PMC3040872.