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MedKoo Cat#: 561768 | Name: Pitofenone HCl
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Description:

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

Pitofenone hydrochloride is an antispasmodic agent. It acts as a potent inhibitor of acetylcholinesterase activity.

Chemical Structure

Pitofenone HCl
Pitofenone HCl
CAS#1248-42-6 (HCl)

Theoretical Analysis

MedKoo Cat#: 561768

Name: Pitofenone HCl

CAS#: 1248-42-6 (HCl)

Chemical Formula: C22H26ClNO4

Exact Mass: 0.0000

Molecular Weight: 403.90

Elemental Analysis: C, 65.42; H, 6.49; Cl, 8.78; N, 3.47; O, 15.84

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 550.00 2 Weeks
100mg USD 1,350.00 2 Weeks
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Related CAS #
54063-52-4 (free base) 1248-42-6 (HCl)
Synonym
Pitofenone hydrochloride; Pitofenone HCl; Baralginketone; Bulgarketone;
IUPAC/Chemical Name
Methyl 2-[4-(2-piperidin-1-ylethoxy)benzoyl]benzoate hydrochloride
InChi Key
ZRFIFDFEDPJBII-UHFFFAOYSA-N
InChi Code
InChI=1S/C22H25NO4.ClH/c1-26-22(25)20-8-4-3-7-19(20)21(24)17-9-11-18(12-10-17)27-16-15-23-13-5-2-6-14-23;/h3-4,7-12H,2,5-6,13-16H2,1H3;1H
SMILES Code
O=C(OC)C1=CC=CC=C1C(C2=CC=C(OCCN3CCCCC3)C=C2)=O.[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
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:
Pitofenone hydrochloride, a spasmolytic compound, inhibits the acetylcholinesterase (AChE) activity from bovine erythrocytes and from electric eel with Kis of 36 and 45 μM.
In vitro activity:
Pitofenone, a spasmolytic compound, inhibited the acetylcholinesterase activity from bovine erythrocytes and from electric eel. It is a potent inhibitor of this enzyme from the two sources, with Ki values of 36 and 45 microM, respectively. Of the five compounds structurally related to pitofenone, only those containing a piperidine moiety show acetylcholinesterase inhibition. All these inhibitions are reversible, linear, and noncompetitive in nature. Reference: Biotechnol Appl Biochem. 1991 Dec;14(3):378-82. https://pubmed.ncbi.nlm.nih.gov/1777122/
In vivo activity:
TBD
Solvent mg/mL mM comments
Solubility
DMF 30.0 74.28
DMSO 54.2 134.10
Ethanol 30.0 74.28
Ethanol:PBS (pH 7.2) (1:5) 0.2 0.40
Water 100.0 247.58
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 403.90 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:
Punekar NS, Kulkarni AV. Acetylcholinesterase inhibition by pitofenone: a spasmolytic compound. Biotechnol Appl Biochem. 1991 Dec;14(3):378-82. PMID: 1777122.
In vitro protocol:
Punekar NS, Kulkarni AV. Acetylcholinesterase inhibition by pitofenone: a spasmolytic compound. Biotechnol Appl Biochem. 1991 Dec;14(3):378-82. PMID: 1777122.
In vivo protocol:
TBD
1: Xiao Y, Wu F, Tang L, Zhang X, Wei M, Wang G, Feng JJ. Divergent Synthesis of Sulfur-Containing Bridged Cyclobutanes by Lewis Acid Catalyzed Formal Cycloadditions of Pyridinium 1,4-Zwitterionic Thiolates and Bicyclobutanes. Angew Chem Int Ed Engl. 2024 May 31:e202408578. doi: 10.1002/anie.202408578. Epub ahead of print. PMID: 38818620. 2: Grigorescu BL, Saplacan I, Morariu MR. Previously undiagnosed serotonin toxicity: From pre-anaesthetic assessment to postoperative management - a case report. J Pak Med Assoc. 2022 Apr;72(4):758-760. doi: 10.47391/JPMA.3806. PMID: 35614617. 3: Sagadevan A, Charpe VP, Ragupathi A, Hwang KC. Visible Light Copper Photoredox-Catalyzed Aerobic Oxidative Coupling of Phenols and Terminal Alkynes: Regioselective Synthesis of Functionalized Ketones via C≡C Triple Bond Cleavage. J Am Chem Soc. 2017 Mar 1;139(8):2896-2899. doi: 10.1021/jacs.6b13113. Epub 2017 Feb 15. PMID: 28177239. 4: Suchand B, Satyanarayana G. Palladium-Catalyzed Environmentally Benign Acylation. J Org Chem. 2016 Aug 5;81(15):6409-23. doi: 10.1021/acs.joc.6b01064. Epub 2016 Jul 19. PMID: 27377566. 5: Vojta J, Hanzlík P, Jedlička A, Coufal P. Separation and determination of impurities in paracetamol, codeine and pitophenone in the presence of fenpiverinium in combined suppository dosage form. J Pharm Biomed Anal. 2015 Jan;102:85-92. doi: 10.1016/j.jpba.2014.09.002. Epub 2014 Sep 16. PMID: 25255449. 6: Miao J, Ge H. Palladium-catalyzed chemoselective decarboxylative ortho acylation of benzoic acids with α-oxocarboxylic acids. Org Lett. 2013 Jun 21;15(12):2930-3. doi: 10.1021/ol400919u. Epub 2013 May 30. PMID: 23721458. 7: Kulkarni SK, Patil CS, Jain NK, Singh A. Modulatory effect of diclofenac on antispasmodic effect of pitofenone in cholinergic spasm. Indian J Exp Biol. 2004 Jun;42(6):567-9. PMID: 15260106. 8: Chaudhary A, Gupta RL. Double blind, randomised, parallel, prospective, comparative, clinical evaluation of a combination of antispasmodic analgesic Diclofenac + Pitofenone + Fenpiverinium (Manyana vs Analgin + Pitofenone + Fenpiverinium (Baralgan) in biliary, ureteric and intestinal colic. J Indian Med Assoc. 1999 Jun;97(6):244-5. PMID: 10645700. 9: Golhar KB, Gupta RL. Open labelled evaluation of injection Manyana (a combination of diclofenac + pitofenone + fenpiverinium) in ureteric, biliary and intestinal spasm--a preliminary report. J Indian Med Assoc. 1999 Sep;97(9):398-400. PMID: 10638099. 10: Chaudhary A, Gupta RL. Double blind, randomised, parallel, prospective, comparative, clinical evaluation of a combination of antispasmodic analgesic Diclofenac + Pitofenone + Fenpiverinium (Manyana) vs Analgin + Pitofenone + Fenpiverinium (Baralgan) in biliary, ureteric and intestinal colic. J Indian Med Assoc. 1999 Feb;97(2):72-5. PMID: 10549201. 11: Chaudhary A, Gupta RL. Double-blind comparative prospective clinical evaluation of a combination antispasmodic--Manyana (R) (diclofenac pitafenone and fenpeverinium) and Baralgan (analgin + pitafenone and fenpeverinium) in intestinal, biliary and ureteric colic. J Indian Med Assoc. 1998 Nov;96(11):359-60. PMID: 10218327. 12: Nikoda VV. Primenenie otechestvennogo analgetika prosidola v posleoperatsionnom periode [Use of a Russian analgesic prosidol in the postoperative period]. Anesteziol Reanimatol. 1997 Sep-Oct;(5):102-3. Russian. PMID: 9432883. 13: Bal-Tembe S, Bhedi DN, Mishra AK, Rajagopalan R, Ghate AV, Subbarayan P, Punekar NS, Kulkarni AV. HL 752: a potent and long-acting antispasmodic agent. Bioorg Med Chem. 1997 Jul;5(7):1381-7. doi: 10.1016/s0968-0896(97)00067-9. PMID: 9377098. 14: Stepanov VN, Mumladze RB, Kadyrov ZA, Perel'man VM, Rozikov IuSh, Tomkevich BA, Puzhik AM, Kosachenko VM. Laparoskopicheskoe lechenie varikotsele [The laparoscopic treatment of varicocele]. Urol Nefrol (Mosk). 1997 Jan-Feb;(1):3-5. Russian. PMID: 9123663. 15: Pinto Pereira LM. A fixed drug eruption to Baralgin (dipyrone) tablets. West Indian Med J. 1994 Dec;43(4):146-7. PMID: 7900381. 16: Puchmeltr P. Ucinné kompozitní spazmoanalgetikum Algifen--výsledky klinických zkousek v gynekologii [An effective composite spasmo-analgesic, Algifen--results of a clinical trial in gynecology]. Cesk Gynekol. 1992 Jun;57(5):219-21. Czech. PMID: 1423710. 17: Priĭma OB. Klinika i lechenie v ambulatornykh usloviiakh lekarstvennogo anafilakticheskogo shoka s blagopriiatnym techeniem [The clinical picture and ambulatory treatment of drug-induced anaphylactic shock with a favorable course]. Feldsher Akush. 1991 Dec;56(12):33-5. Russian. PMID: 1790796. 18: Punekar NS, Kulkarni AV. Acetylcholinesterase inhibition by pitofenone: a spasmolytic compound. Biotechnol Appl Biochem. 1991 Dec;14(3):378-82. PMID: 1777122. 19: Marthak KV, Gokarn AM, Rao AV, Sane SP, Mahanta RK, Sheth RD, Chavda KD, Rane BS, Vaidya AB. A multi-centre comparative study of diclofenac sodium and a dipyrone/spasmolytic combination, and a single-centre comparative study of diclofenac sodium and pethidine in renal colic patients in India. Curr Med Res Opin. 1991;12(6):366-73. doi: 10.1185/03007999109111506. PMID: 2044396. 20: Añez MS, Martínez D, Pacheco JL, González H, Rivera J, Pelaschier E, Uzcátegui L, Romero MD, Molina Z, Roditti de Montilla M, et al. Indometacina en el tratamiento de la colecistitis aguda y cólico biliar [Indomethacin in the treatment of acute cholecystitis and biliary colic]. G E N. 1991 Jan- Mar;45(1):32-7. Spanish. PMID: 1843681.