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MedKoo Cat#: 414114 | Name: Profenamine HCl
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Description:

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

Profenamine HCl is an Antiparkinsonian and potential redox indicators in the titration of hydroquinone, metol and ascorbic acid with chloramine-T and chloramine-B in sulphuric, hydrochloric and acetic acid media.

Chemical Structure

Profenamine HCl
Profenamine HCl
CAS#1094-08-2 (HCl)

Theoretical Analysis

MedKoo Cat#: 414114

Name: Profenamine HCl

CAS#: 1094-08-2 (HCl)

Chemical Formula: C19H25ClN2S

Exact Mass: 0.0000

Molecular Weight: 348.93

Elemental Analysis: C, 65.40; H, 7.22; Cl, 10.16; N, 8.03; S, 9.19

Price and Availability

Size Price Availability Quantity
25mg USD 300.00 2 Weeks
50mg USD 450.00 2 Weeks
100mg USD 850.00 2 Weeks
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Related CAS #
1094-08-2 (HCl) 522-00-9 (free base)
Synonym
Profenamine HCl; Profenamine hydrochloride; NSC64074; NSC-64074; NSC 64074; NSC-169467; NSC169467; NSC 169467; Ethopropazine hydrochloride; Ethopropazine HCl; Parphezein; Isothazine hydrochloride; Lysivane hydrochloride;
IUPAC/Chemical Name
10H-Phenothiazine-10-ethanamine, N,N-diethyl-alpha-methyl-, monohydrochloride
InChi Key
VXPCQISYVPFYRK-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H24N2S.ClH/c1-4-20(5-2)15(3)14-21-16-10-6-8-12-18(16)22-19-13-9-7-11-17(19)21;/h6-13,15H,4-5,14H2,1-3H3;1H
SMILES Code
CC(N(CC)CC)CN1C2=C(C=CC=C2)SC3=CC=CC=C13.[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, DMF, and ethanol
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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:
Profenamine HCl possess anticholinergic, antihistamine and antiadrenergic properties. It is a BChE inhibitor (IC50 = 15.14 uM in human erythrocyte lysates). It is selective for BChE over AChE.
In vitro activity:
Profenamine may play a role in modulating the catalytic activity of the recombinant antibody fragment, having potential as an antidote against organophosphate poisoning. This study investigates the activity of ethopropazine as a selective inhibitor of BChE. The study aimed to develop a recombinant antibody fragment (WZ1-14.2.1) with BChE-like catalytic activity. Profenamine was used to inhibit the enzymatic activity of WZ1-14.2.1. Reference: MAbs. 2014 Jul-Aug;6(4):1084-93. https://pubmed.ncbi.nlm.nih.gov/24675419/
In vivo activity:
Profenamine displayed potent anti-nicotinic properties in a mouse model. Profenamine effectively prevented nicotine-induced convulsions and had an ED50 value of 4.9 mg/kg. Profenamine demonstrated both competitive and non-competitive properties when antagonizing nicotine-induced convulsions. Profenamine is an anticholinergic compound that mitigates the effects of nicotine-induced convulsions. Reference: J Pharm Pharmacol. 1998 Nov;50(11):1299-305. https://pubmed.ncbi.nlm.nih.gov/9877318/
Solvent mg/mL mM
Solubility
DMF 10.0 28.66
DMSO 5.0 14.33
Ethanol 5.0 14.33
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 348.93 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. Podestà A, Rossi S, Massarelli I, Carpi S, Adinolfi B, Fogli S, Bianucci AM, Nieri P. Selection of a human butyrylcholinesterase-like antibody single-chain variable fragment resistant to AChE inhibitors from a phage library expressed in E. coli. MAbs. 2014 Jul-Aug;6(4):1084-93. doi: 10.4161/mabs.28635. PMID: 24675419; PMCID: PMC4171011. 2. Inazu M, Yamada T, Kubota N, Yamanaka T. Functional expression of choline transporter-like protein 1 (CTL1) in small cell lung carcinoma cells: a target molecule for lung cancer therapy. Pharmacol Res. 2013 Oct;76:119-31. doi: 10.1016/j.phrs.2013.07.011. Epub 2013 Aug 13. PMID: 23948665. 3. Gao ZG, Liu BY, Cui WY, Li LJ, Fan QH, Liu CG. Anti-nicotinic properties of anticholinergic antiparkinson drugs. J Pharm Pharmacol. 1998 Nov;50(11):1299-305. doi: 10.1111/j.2042-7158.1998.tb03349.x. PMID: 9877318. 4. Jevtovic-Todorovic V, Meyenburg AP, Olney JW, Wozniak DF. Anti-parkinsonian agents procyclidine and ethopropazine alleviate thermal hyperalgesia in neuropathic rats. Neuropharmacology. 2003 May;44(6):739-48. doi: 10.1016/s0028-3908(03)00069-8. PMID: 12681372.
In vitro protocol:
1. Podestà A, Rossi S, Massarelli I, Carpi S, Adinolfi B, Fogli S, Bianucci AM, Nieri P. Selection of a human butyrylcholinesterase-like antibody single-chain variable fragment resistant to AChE inhibitors from a phage library expressed in E. coli. MAbs. 2014 Jul-Aug;6(4):1084-93. doi: 10.4161/mabs.28635. PMID: 24675419; PMCID: PMC4171011. 2. Inazu M, Yamada T, Kubota N, Yamanaka T. Functional expression of choline transporter-like protein 1 (CTL1) in small cell lung carcinoma cells: a target molecule for lung cancer therapy. Pharmacol Res. 2013 Oct;76:119-31. doi: 10.1016/j.phrs.2013.07.011. Epub 2013 Aug 13. PMID: 23948665.
In vivo protocol:
1. Gao ZG, Liu BY, Cui WY, Li LJ, Fan QH, Liu CG. Anti-nicotinic properties of anticholinergic antiparkinson drugs. J Pharm Pharmacol. 1998 Nov;50(11):1299-305. doi: 10.1111/j.2042-7158.1998.tb03349.x. PMID: 9877318. 2. Jevtovic-Todorovic V, Meyenburg AP, Olney JW, Wozniak DF. Anti-parkinsonian agents procyclidine and ethopropazine alleviate thermal hyperalgesia in neuropathic rats. Neuropharmacology. 2003 May;44(6):739-48. doi: 10.1016/s0028-3908(03)00069-8. PMID: 12681372.
1: Estévez J, Selva V, Benabent M, Mangas I, Sogorb MÁ, Vilanova E. Acetylcholine-hydrolyzing activities in soluble brain fraction: Characterization with reversible and irreversible inhibitors. Chem Biol Interact. 2016 Nov 25;259(Pt B):374-381. doi: 10.1016/j.cbi.2016.08.004. Epub 2016 Aug 6. PubMed PMID: 27507601. 2: Mangas I, Radić Z, Taylor P, Ghassemian M, Candela H, Vilanova E, Estévez J. Butyrylcholinesterase identification in a phenylvalerate esterase-enriched fraction sensitive to low mipafox concentrations in chicken brain. Arch Toxicol. 2017 Feb;91(2):909-919. doi: 10.1007/s00204-016-1670-6. Epub 2016 Feb 2. PubMed PMID: 26838044. 3: Bahar FG, Imai T. Aspirin hydrolysis in human and experimental animal plasma and the effect of metal cations on hydrolase activities. Drug Metab Dispos. 2013 Jul;41(7):1450-6. doi: 10.1124/dmd.113.051805. Epub 2013 May 6. PubMed PMID: 23649702. 4: Tvarijonaviciute A, Ceron JJ, Tecles F. Acetylcholinesterase and butyrylcholinesterase activities in obese Beagle dogs before and after weight loss. Vet Clin Pathol. 2013 Jun;42(2):207-11. doi: 10.1111/vcp.12032. Epub 2013 Apr 1. PubMed PMID: 23550593. 5: Kumagai H, Suemori H, Uesugi M, Nakatsuji N, Kawase E. Identification of small molecules that promote human embryonic stem cell self-renewal. Biochem Biophys Res Commun. 2013 May 17;434(4):710-6. doi: 10.1016/j.bbrc.2013.03.061. Epub 2013 Mar 27. PubMed PMID: 23541943. 6: Naik RS, Liu W, Saxena A. Development and validation of a simple assay for the determination of cholinesterase activity in whole blood of laboratory animals. J Appl Toxicol. 2013 Apr;33(4):290-300. doi: 10.1002/jat.2730. Epub 2012 Mar 12. PubMed PMID: 22407886. 7: Sinko G, Kovarik Z, Reiner E, Simeon-Rudolf V, Stojan J. Mechanism of stereoselective interaction between butyrylcholinesterase and ethopropazine enantiomers. Biochimie. 2011 Oct;93(10):1797-807. doi: 10.1016/j.biochi.2011.06.023. Epub 2011 Jun 29. PubMed PMID: 21740955. 8: Kiselyuk A, Farber-Katz S, Cohen T, Lee SH, Geron I, Azimi B, Heynen-Genel S, Singer O, Price J, Mercola M, Itkin-Ansari P, Levine F. Phenothiazine neuroleptics signal to the human insulin promoter as revealed by a novel high-throughput screen. J Biomol Screen. 2010 Jul;15(6):663-70. doi: 10.1177/1087057110372257. Epub 2010 Jun 14. PubMed PMID: 20547533; PubMed Central PMCID: PMC3374493. 9: Yücel YY, Tacal O, Ozer I. Comparative effects of cationic triarylmethane, phenoxazine and phenothiazine dyes on horse serum butyrylcholinesterase. Arch Biochem Biophys. 2008 Oct 15;478(2):201-5. doi: 10.1016/j.abb.2008.07.006. Epub 2008 Jul 16. PubMed PMID: 18656440. 10: Liao WS, Lin CH, Chen CY, Kuo CM, Liu YC, Wu JC, Lin CE. Enantioseparation of phenothiazines in CD-modified CZE using single isomer sulfated CD as a chiral selector. Electrophoresis. 2007 Nov;28(21):3922-9. PubMed PMID: 17922499. 11: Tanaka E, Nakamura T, Terada M, Shinozuka T, Hashimoto C, Kurihara K, Honda K. Simple and simultaneous determination for 12 phenothiazines in human serum by reversed-phase high-performance liquid chromatography. J Chromatogr B Analyt Technol Biomed Life Sci. 2007 Jul 1;854(1-2):116-20. Epub 2007 Apr 13. PubMed PMID: 17459789. 12: Shayeganpour A, Somayaji V, Brocks DR. A liquid chromatography-mass spectrometry assay method for simultaneous determination of amiodarone and desethylamiodarone in rat specimens. Biomed Chromatogr. 2007 Mar;21(3):284-90. PubMed PMID: 17221913. 13: Lee DW, Choi JY, Kim WT, Je YH, Song JT, Chung BK, Boo KS, Koh YH. Mutations of acetylcholinesterase1 contribute to prothiofos-resistance in Plutella xylostella (L.). Biochem Biophys Res Commun. 2007 Feb 16;353(3):591-7. Epub 2006 Dec 21. PubMed PMID: 17196934. 14: Persyn JT, McDonough JA, Nino JA, Dixon H, Boland EJ. Mucosal delivery of cytotoxic therapeutic agents: response of rat nasal mucosa to microencapsulated ethopropazine HCl enantiomer. J Microencapsul. 2005 Nov;22(7):737-44. PubMed PMID: 16421084. 15: Reiner E, Bosak A, Simeon-Rudolf V. Activity of cholinesterases in human whole blood measured with acetylthiocholine as substrate and ethopropazine as selective inhibitor of plasma butyrylcholinesterase. Arh Hig Rada Toksikol. 2004 Apr;55(1):1-4. PubMed PMID: 15137175. 16: Lin CE, Liao WS, Chen KH. Enantioseparation of phenothiazines in cyclodextrin-modified capillary zone electrophoresis: reversal of migration order. Electrophoresis. 2003 Sep;24(18):3139-46. PubMed PMID: 14518036. 17: Jevtovic-Todorovic V, Meyenburg AP, Olney JW, Wozniak DF. Anti-parkinsonian agents procyclidine and ethopropazine alleviate thermal hyperalgesia in neuropathic rats. Neuropharmacology. 2003 May;44(6):739-48. PubMed PMID: 12681372. 18: Sinko G, Novak P, Ziher D, Vinković V, Sunjić V, Simeon-Rudolf V. Separation, conformation in solution and absolute configuration of ethopropazine enantiomers. Enantiomer. 2002 Mar-Jun;7(2-3):149-56. PubMed PMID: 12108633. 19: Darvesh S, MacKnight C, Rockwood K. Butyrylcholinesterase and cognitive function. Int Psychogeriatr. 2001 Dec;13(4):461-4. PubMed PMID: 12003252. 20: Golicnik M, Sinko G, Simeon-Rudolf V, Grubic Z, Stojan J. Kinetic model of ethopropazine interaction with horse serum butyrylcholinesterase and its docking into the active site. Arch Biochem Biophys. 2002 Feb 1;398(1):23-31. PubMed PMID: 11811945. 21: Gowda HS, Mohan BM, Ahmed SA. N-substituted phenothiazines as redox indicators in titrations with chloramine-T and chloramine-B. Talanta. 1980 Dec;27(12):1084-6. doi: 10.1016/0039-9140(80)80254-2. PMID: 18962802.

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