Pramoxine HCl | Pramocaine | CAS#140-65-8 | CAS#637-58-1 | Anesthetic

MedKoo Cat#: 531033 | Name: Pramoxine HCl

Featured

Description:

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

Pramoxine, also known as Pramocaine, is a topical anesthetic. Pramoxine decreases the permeability of the neuronal membrane to sodium ions by reversibly binding to and inhibiting voltage-gated sodium channels. This results in stabilization of the membrane and, thereby inhibiting the ionic fluxes required for membrane depolarization, hence resulting in the failure to initiate a propagated action potential and subsequent conduction blockade.

Chemical Structure

Pramoxine HCl

CAS#637-58-1 (HCl)

Theoretical Analysis

MedKoo Cat#: 531033

Name: Pramoxine HCl

CAS#: 637-58-1 (HCl)

Chemical Formula: C17H28ClNO3

Exact Mass: 293.1991

Molecular Weight: 329.87

Elemental Analysis: C, 61.90; H, 8.56; Cl, 10.75; N, 4.25; O, 14.55

Price and Availability

Size	Price	Availability	Quantity
5g	USD 350.00	2 weeks
25g	USD 650.00	2 weeks

Bulk Inquiry

Buy Now

Add to Cart

Related CAS #

140-65-8 (free) 637-58-1 (HCl)

Synonym

Pramoxine, Pramoxine HCl, Pramoxine hydrochloride, Tronothane, Tronopthane; Pramoxine HCl

IUPAC/Chemical Name

4-(3-(4-butoxyphenoxy)propyl)morpholine hydrochloride

InChi Key

SYCBXBCPLUFJID-UHFFFAOYSA-N

InChi Code

InChI=1S/C17H27NO3.ClH/c1-2-3-12-20-16-5-7-17(8-6-16)21-13-4-9-18-10-14-19-15-11-18;/h5-8H,2-4,9-15H2,1H3;1H

SMILES Code

CCCCOC1=CC=C(OCCCN2CCOCC2)C=C1.[H]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

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:

Pramocaine hydrochloride decreases the permeability of neuronal membranes to sodium ions, blocking both initiation and conduction of nerve impulses.

In vitro activity:

TBD

In vivo activity:

This study showed that pramoxine, as well as lidocaine produced skin antinociception in a dose-related fashion. The relative potency (ED50 [50% effective dose] basis) was lidocaine (5.44 [4.67-6.35] μmol) greater than pramoxine (42.1 [38.8-45.7] μmol) (p < 0.01). On the basis of equianalgesic doses (ED75, ED50, and ED25), pramoxine caused equivalent duration of cutaneous antinociception to lidocaine. These preclinical data indicated that pramoxine elicits skin antinociception dose-relatedly. Pramoxine exhibits a potency less than that of lidocaine while they have a comparable duration of skin antinociceptive action. Reference: Pharmacol Rep. 2018 Dec;70(6):1180-1184. https://pubmed.ncbi.nlm.nih.gov/30326418/

	Solvent	mg/mL	mM
Solubility
	DMF	5.0	15.16
	DMSO	57.0	172.80
	Ethanol	40.5	122.78
	Ethanol:PBS (pH 7.2) (1:5)	0.2	0.49
	Water	83.0	251.62

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 329.87 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. Chou AK, Chiu CC, Chen YW, Wang JJ, Hung CH. Skin nociceptive block with pramoxine delivery by subcutaneous injection in rats. Pharmacol Rep. 2018 Dec;70(6):1180-1184. doi: 10.1016/j.pharep.2018.09.001. Epub 2018 Sep 10. PMID: 30326418. 2. Chou AK, Chiu CC, Han MM, Chen YW, Wang JJ, Hung CH. Intrathecal pramoxine causes long-lasting spinal sensory and motor block in rats. J Pharm Pharmacol. 2018 Apr;70(4):543-549. doi: 10.1111/jphp.12894. Epub 2018 Feb 13. PMID: 29441574.

In vitro protocol:

TBD

In vivo protocol:

1: Kim SJ, Goldberg BJ. Anaphylaxis due to topical pramoxine. Ann Allergy Asthma Immunol. 2015 Jan;114(1):72-3. doi: 10.1016/j.anai.2014.10.011. Epub 2014 Nov 14. PubMed PMID: 25457867. 2: Hylwa SA, Warshaw E. Contact allergy to pramoxine (pramocaine): the importance of testing to personal products. Dermatitis. 2014 May-Jun;25(3):147-8. doi: 10.1097/DER.0000000000000038. PubMed PMID: 24819289. 3: Ramadan NK, Merey HA. Ion-Selective Electrodes for the Potentiometric Determination of Pramoxine HCl Using Different Ionophores. Acta Chim Slov. 2012 Dec;59(4):870-8. PubMed PMID: 24061370. 4: Kircik LH. Efficacy and onset of action of hydrocortisone acetate 2.5% and pramoxine hydrochloride 1% lotion for the management of pruritus: results of a pilot study. J Clin Aesthet Dermatol. 2011 Feb;4(2):48-50. PubMed PMID: 21386957; PubMed Central PMCID: PMC3050616. 5: Tronolane (pramoxine). Med Lett Drugs Ther. 1981 Nov 13;23(23):100. PubMed PMID: 7289977. 6: Ebrahimi N, Vohra S, Gedeon C, Akoury H, Bernstein P, Pairaudeau N, Cormier J, Dontigny L, Arsenault MY, Fortin C, Goyet M, Lafortune C, Lalande J, Beauchamp C, Engel F, Fortin A, Taddio A, Einarson T, Koren G. The fetal safety of hydrocortisone-pramoxine (Proctofoam-HC) for the treatment of hemorrhoids in late pregnancy. J Obstet Gynaecol Can. 2011 Feb;33(2):153-8. Erratum in: J Obstet Gynaecol Can. 2011 May;33(5):436. PubMed PMID: 21352635. 7: Young TA, Patel TS, Camacho F, Clark A, Freedman BI, Kaur M, Fountain J, Williams LL, Yosipovitch G, Fleischer AB Jr. A pramoxine-based anti-itch lotion is more effective than a control lotion for the treatment of uremic pruritus in adult hemodialysis patients. J Dermatolog Treat. 2009;20(2):76-81. doi: 10.1080/09546630802441218. PubMed PMID: 18821119. 8: Grove G, Zerweck C. An evaluation of the moisturizing and anti-itch effects of a lactic acid and pramoxine hydrochloride cream. Cutis. 2004 Feb;73(2):135-9. PubMed PMID: 15027519. 9: Greer IA, Cameron AD. Topical pramoxine and hydrocortisone foam versus placebo in relief of post partum episiotomy symptoms and wound healing. Scott Med J. 1984 Apr;29(2):104-6. PubMed PMID: 6397856. 10: Fisher AA. The safety of pramoxine hydrochloride when used as a topical (surface) anesthetic. Cutis. 1998 Sep;62(3):122-3. PubMed PMID: 9770123. 11: van Ketel WG. Allergy to pramoxine (pramocaine). Contact Dermatitis. 1981 Jan;7(1):49. PubMed PMID: 7249628. 12: Demosthenes LD, Lane AS, Blackhurst DW. Implementing High-Value Care. South Med J. 2015 Nov;108(11):645-8. doi: 10.14423/SMJ.0000000000000360. PubMed PMID: 26539939. 13: Cusano F, Luciano S. Contact dermatitis from pramoxine. Contact Dermatitis. 1993 Jan;28(1):39. PubMed PMID: 8428445. 14: Spiller HA, Baker SD, Smith GW, LoVecchio F. Evaluation of pramoxine ingestion as reported to poison centers. Ann Pharmacother. 2006 May;40(5):996-7. Epub 2006 Apr 4. PubMed PMID: 16595565. 15: Fisher AA. Allergic reactions to topical (surface) anesthetics with reference to the safety of tronothane (pramoxine hydrochloride). Cutis. 1980 Jun;25(6):584, 586, 589-91 passim. PubMed PMID: 7379587. 16: Chang ZL, Boller JP, Pacenti DM, Wong CF. Rapid high-performance liquid chromatographic determination of pramoxine hydrochloride in topical cream and suppositories. J Chromatogr. 1984 May 18;291:428-33. PubMed PMID: 6736170. 17: Yosipovitch G, Maibach HI. Effect of topical pramoxine on experimentally induced pruritus in humans. J Am Acad Dermatol. 1997 Aug;37(2 Pt 1):278-80. PubMed PMID: 9270522. 18: Weinberger R, Mann B, Posluszny J. High-pressure liquid chromatographic analysis of pramoxine hydrochloride in high lipoid aerosol foam dosage form. J Pharm Sci. 1980 Apr;69(4):475-7. PubMed PMID: 7373553. 19: SCHMIDT JL, BLOCKUS LE, RICHARDS RK. The pharmacology of pramoxine hydrochloride: a new topical local anesthetic. Curr Res Anesth Analg. 1953 Nov-Dec;32(6:1):418-25. PubMed PMID: 13107298. 20: Hanretty KP, Davidson SE, Cordiner JW. Clinical evaluation of a topical anaesthetic preparation (pramoxine hydrochloride and hydrocortisone) in post-episiotomy pain relief. Br J Clin Pract. 1984 Nov-Dec;38(11-12):421-2. PubMed PMID: 6529546. 21: NCI thesaurus, https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&code=C61903