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MedKoo Cat#: 531008 | Name: Butamben
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Description:

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

Butamben, also known as Butoform, is a local anesthetic. Blockade of voltage-gated channel expressed in the peripheral sensory neurons has been suggested as a mechanism of action. Butaben effects on another sensory neuronal channel family, transient receptor potential (TRP) have remained unclear. Butamben attenuated acute animal pain behaviors in a TRPA1- or TRPV4-dependent manner. Butamben inhibits the total barium current through expressed calcium channel types in PC12 cells, including Cav1.2/L-type channels.

Chemical Structure

Butamben
Butamben
CAS#94-25-7

Theoretical Analysis

MedKoo Cat#: 531008

Name: Butamben

CAS#: 94-25-7

Chemical Formula: C11H15NO2

Exact Mass: 193.1103

Molecular Weight: 193.25

Elemental Analysis: C, 68.37; H, 7.82; N, 7.25; O, 16.56

Price and Availability

Size Price Availability Quantity
5g USD 250.00 2 Weeks
10g USD 350.00 2 Weeks
25g USD 550.00 2 Weeks
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Related CAS #
No Data
Synonym
Butamben, Butanylcaine, Butesin, Zyljectin, Butoform, Planoform, Scuroform, NSC 128464, NSC-128464, NSC128464
IUPAC/Chemical Name
butyl 4-aminobenzoate
InChi Key
IUWVALYLNVXWKX-UHFFFAOYSA-N
InChi Code
InChI=1S/C11H15NO2/c1-2-3-8-14-11(13)9-4-6-10(12)7-5-9/h4-7H,2-3,8,12H2,1H3
SMILES Code
O=C(OCCCC)C1=CC=C(N)C=C1
Appearance
White to light yellow 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:
Butamben (Butyl 4-aminobenzoate) has local narcotic effect.
In vitro activity:
Butamben 500 microM reversibly suppressed the total whole-cell barium current by 90% +/- 3% (n = 15), whereas 10 microM nifedipine suppressed this barium current by 75% +/- 7% (n = 6). Preexposure to butamben followed by washout decreased the inhibition by nifidepine to 47% +/- 5% (n = 10). Reference: Anesth Analg. 2008 Jun;106(6):1778-83. https://pubmed.ncbi.nlm.nih.gov/18499609/
In vivo activity:
Typical transient T-type barium currents, selectively evoked by low-voltage (-40 mV) clamp stimulation of small (approximately 20 microm diameter) dorsal root ganglion neurons from newborn mice, were inhibited by BAB (butamben) with an IC50 value of approximately 200 microM. Furthermore, 200 microM BAB accelerated T-type current activation, deactivation, and inactivation kinetics, comparable to earlier observations for N-type calcium channels. Finally, 200 microM BAB had no effect on the midpoint potential and slope factor of the activation curve, although it caused a approximately 3 mV hyperpolarizing shift of the inactivation curve, without affecting the slope factor. BAB inhibits T-type calcium channels with a mechanism associated with channel kinetics acceleration. Reference: Anesth Analg. 2006 Jan;102(1):141-5. https://pubmed.ncbi.nlm.nih.gov/16368819/
Solvent mg/mL mM
Solubility
DMSO 69.0 357.06
Ethanol 38.0 196.64
Water 19.0 98.37
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 193.25 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. Rampaart LJ, Beekwilder JP, van Kempen GT, van den Berg RJ, Ypey DL. The local anesthetic butamben inhibits total and L-type barium currents in PC12 cells. Anesth Analg. 2008 Jun;106(6):1778-83. doi: 10.1213/ane.0b013e318172c3a2. PMID: 18499609. 2. Winkelman DL, Beck CL, Ypey DL, O'Leary ME. Inhibition of the A-type K+ channels of dorsal root ganglion neurons by the long-duration anesthetic butamben. J Pharmacol Exp Ther. 2005 Sep;314(3):1177-86. doi: 10.1124/jpet.105.087759. Epub 2005 May 27. PMID: 15923341. 3. Beekwilder JP, van Kempen GT, van den Berg RJ, Ypey DL. The local anesthetic butamben inhibits and accelerates low-voltage activated T-type currents in small sensory neurons. Anesth Analg. 2006 Jan;102(1):141-5. doi: 10.1213/01.ane.0000189599.79451.34. PMID: 16368819.
In vitro protocol:
1. Rampaart LJ, Beekwilder JP, van Kempen GT, van den Berg RJ, Ypey DL. The local anesthetic butamben inhibits total and L-type barium currents in PC12 cells. Anesth Analg. 2008 Jun;106(6):1778-83. doi: 10.1213/ane.0b013e318172c3a2. PMID: 18499609. 2. Winkelman DL, Beck CL, Ypey DL, O'Leary ME. Inhibition of the A-type K+ channels of dorsal root ganglion neurons by the long-duration anesthetic butamben. J Pharmacol Exp Ther. 2005 Sep;314(3):1177-86. doi: 10.1124/jpet.105.087759. Epub 2005 May 27. PMID: 15923341.
In vivo protocol:
1. Beekwilder JP, van Kempen GT, van den Berg RJ, Ypey DL. The local anesthetic butamben inhibits and accelerates low-voltage activated T-type currents in small sensory neurons. Anesth Analg. 2006 Jan;102(1):141-5. doi: 10.1213/01.ane.0000189599.79451.34. PMID: 16368819.
1: Cereda CM, Franz-Montan M, da Silva CM, Casadei BR, Domingues CC, Tofoli GR, de Araujo DR, de Paula E. Transdermal delivery of butamben using elastic and conventional liposomes. J Liposome Res. 2013 Sep;23(3):228-34. doi: 10.3109/08982104.2013.796975. Epub 2013 May 22. PubMed PMID: 23697904. 2: Bang S, Yang TJ, Yoo S, Heo TH, Hwang SW. Inhibition of sensory neuronal TRPs contributes to anti-nociception by butamben. Neurosci Lett. 2012 Jan 11;506(2):297-302. doi: 10.1016/j.neulet.2011.11.026. Epub 2011 Nov 23. PubMed PMID: 22133806. 3: Shulman M, Joseph NJ, Haller CA. Effect of epidural and subarachnoid injections of a 10% butamben suspension. Reg Anesth. 1990 May-Jun;15(3):142-6. PubMed PMID: 2265169. 4: Rampaart LJ, Beekwilder JP, van Kempen GT, van den Berg RJ, Ypey DL. The local anesthetic butamben inhibits total and L-type barium currents in PC12 cells. Anesth Analg. 2008 Jun;106(6):1778-83. doi: 10.1213/ane.0b013e318172c3a2. PubMed PMID: 18499609. 5: Kim HJ, Park M, Han YM, Kwon BM, Kim SH. Butamben derivatives enhance BMP-2-stimulated commitment of C2C12 cells into osteoblasts with induction of voltage-gated potassium channel expression. Bioorg Med Chem Lett. 2011 Dec 15;21(24):7363-6. doi: 10.1016/j.bmcl.2011.10.020. Epub 2011 Oct 13. PubMed PMID: 22041064. 6: Mitchell VA, White DM, Cousins MJ. The long-term effect of epidural administration of butamben suspension on nerve injury-induced allodynia in rats. Anesth Analg. 1999 Oct;89(4):989-94. PubMed PMID: 10512277. 7: Kolesnikov YA, Cristea M, Pasternak GW. Analgesic synergy between topical morphine and butamben in mice. Anesth Analg. 2003 Oct;97(4):1103-7, table of contents. PubMed PMID: 14500165. 8: Shulman M, Lubenow TR, Nath HA, Blazek W, McCarthy RJ, Ivankovich AD. Nerve blocks with 5% butamben suspension for the treatment of chronic pain syndromes. Reg Anesth Pain Med. 1998 Jul-Aug;23(4):395-401. PubMed PMID: 9690593. 9: Armstrong DG, Kanat IO. Analgesic efficacy of topical butamben picrate. J Am Podiatr Med Assoc. 1995 Dec;85(12):738-40. PubMed PMID: 8592284. 10: Nakano M, Juni K, Arita T. Controlled drug permeation I: controlled release of butamben through silicone membrane by complexation. J Pharm Sci. 1976 May;65(5):709-12. PubMed PMID: 932939. 11: Paloncýová M, DeVane RH, Murch BP, Berka K, Otyepka M. Rationalization of reduced penetration of drugs through ceramide gel phase membrane. Langmuir. 2014 Nov 25;30(46):13942-8. doi: 10.1021/la503289v. Epub 2014 Nov 11. PubMed PMID: 25354090. 12: Ginsburg EJ, Stephens DA, West PR, Buko AM, Robinson DH, Li LC, Bommireddi AR. Identification of a yellow impurity in aged samples of aqueous butamben suspension: evidence for the oxidative degradation of poly(ethylene glycol). J Pharm Sci. 2000 Jun;89(6):766-70. PubMed PMID: 10824135. 13: Kuroda Y, Nasu H, Fujiwara Y, Nakagawa T. Orientations and locations of local anesthetics benzocaine and butamben in phospholipid membranes as studied by 2H NMR spectroscopy. J Membr Biol. 2000 Sep 15;177(2):117-28. PubMed PMID: 11003686. 14: Winkelman DL, Beck CL, Ypey DL, O'Leary ME. Inhibition of the A-type K+ channels of dorsal root ganglion neurons by the long-duration anesthetic butamben. J Pharmacol Exp Ther. 2005 Sep;314(3):1177-86. Epub 2005 May 27. PubMed PMID: 15923341. 15: Shulman M, Harris JE, Lubenow TR, Nath HA, Ivankovich AD. Comparison of epidural butamben to celiac plexus neurolytic block for the treatment of the pain of pancreatic cancer. Clin J Pain. 2000 Dec;16(4):304-9. PubMed PMID: 11153785. 16: Beekwilder JP, van Kempen GT, van den Berg RJ, Ypey DL. The local anesthetic butamben inhibits and accelerates low-voltage activated T-type currents in small sensory neurons. Anesth Analg. 2006 Jan;102(1):141-5. PubMed PMID: 16368819. 17: McCarthy RJ, Kerns JM, Nath HA, Shulman M, Ivankovich AD. The antinociceptive and histologic effect of sciatic nerve blocks with 5% butamben suspension in rats. Anesth Analg. 2002 Mar;94(3):711-6; table of contents. PubMed PMID: 11867403. 18: Thériault O, Poulin H, Sculptoreanu A, de Groat WC, O'Leary ME, Chahine M. Modulation of peripheral Na(+) channels and neuronal firing by n-butyl-p-aminobenzoate. Eur J Pharmacol. 2014 Mar 15;727:158-66. doi: 10.1016/j.ejphar.2014.01.036. Epub 2014 Jan 30. PubMed PMID: 24486399. 19: Maestrelli F, González-Rodríguez ML, Rabasco AM, Ghelardini C, Mura P. New "drug-in cyclodextrin-in deformable liposomes" formulations to improve the therapeutic efficacy of local anaesthetics. Int J Pharm. 2010 Aug 16;395(1-2):222-31. doi: 10.1016/j.ijpharm.2010.05.046. Epub 2010 Jun 8. PubMed PMID: 20594944. 20: Cereda CM, Guilherme VA, Alkschbirs MI, de Brito Junior RB, Tofoli GR, Franz-Montan M, de Araujo DR, de Paula E. Liposomal butamben gel formulations: toxicity assays and topical anesthesia in an animal model. J Liposome Res. 2017 Mar;27(1):74-82. doi: 10.3109/08982104.2016.1160924. Epub 2016 Apr 28. PubMed PMID: 27126194.