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MedKoo Cat#: 329526 | Name: Pirmenol
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Description:

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

Pirmenol is an antiarrhythmic agent. Pirmenol inhibits muscarinic acetylcholine receptor-operated K+ current in the guinea pig heart. Pirmenol is active in a variety of experimental arrhythmic models of diverse etiology and has a favorable therapeutic index compared with other class I agents. Pirmenol is highly efficacious whether the arrhythmias were atrial or ventricular in origin, chemically, mechanically or electrically induced or of the automaticity or reentrant types.

Chemical Structure

Pirmenol
Pirmenol
CAS#68252-19-7 (free base)

Theoretical Analysis

MedKoo Cat#: 329526

Name: Pirmenol

CAS#: 68252-19-7 (free base)

Chemical Formula: C22H30N2O

Exact Mass: 338.2358

Molecular Weight: 338.50

Elemental Analysis: C, 78.06; H, 8.93; N, 8.28; O, 4.73

Price and Availability

Size Price Availability Quantity
10mg USD 150.00 Ready to ship
25mg USD 250.00 Ready to ship
50mg USD 450.00 Ready to ship
100mg USD 750.00 Ready to ship
200mg USD 1,250.00 Ready to ship
500mg USD 2,450.00 Ready to ship
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Related CAS #
78774-24-0 (racemic) 68252-19-7 (free base) 61477-94-9 (HCl) 82734-31-4 (xHCl)
Synonym
Pirmenol; Cl 845; Cl-845; Cl845; Pirmavar.
IUPAC/Chemical Name
4-((2R,6S)-2,6-dimethylpiperidin-1-yl)-1-phenyl-1-(pyridin-2-yl)butan-1-ol
InChi Key
APUDBKTWDCXQJA-QIDMFYOTSA-N
InChi Code
InChI=1S/C22H30N2O/c1-18-10-8-11-19(2)24(18)17-9-15-22(25,20-12-4-3-5-13-20)21-14-6-7-16-23-21/h3-7,12-14,16,18-19,25H,8-11,15,17H2,1-2H3/t18-,19+,22?
SMILES Code
OC(C1=NC=CC=C1)(C2=CC=CC=C2)CCCN3[C@H](C)CCC[C@@H]3C
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
Biological target:
Pirmenol hydrochloride inhibits IK.ACh by blocking muscarinic receptors. The IC50 of Pirmenol for inhibition of Carbachol-induced IK.ACh is 0.1 μM.
In vitro activity:
Pirmenol inhibits the carbachol-induced IK.ACh in a concentration-dependent manner. Pirmenol also inhibits the GTPγS-induced current although the concentrations of Pirmenol needed to inhibit the GTPγS-induced current are much higher than those to inhibit the carbachol-induced IK.ACh. The IC50 of Pirmenol for inhibition of the GTPγS-induced currents is 30 μM. The inhibitory effect of Pirmenol on these IK.ACh is almost completely reversible and the outward current reappeared upon washout of Pirmenol. Pirmenol on the muscarinic acetylcholine receptor-operated K+ current (IK.ACh) in atrial cells and on experimental atrial fibrillation in isolated guinea-pig hearts. In isolated atrial myocytes, Pirmenol concentration dependently inhibits the IK.ACh induced by carbachol or intracellular loading of GTPγS. In Langendorff-perfused hearts Pirmenol reverses the carbachol-induced decreases in effective refractory periods and atrial fibrillation threshold. Reference: Eur J Pharmacol. 1997 Oct 29;338(1):71-4. https://linkinghub.elsevier.com/retrieve/pii/S0014-2999(97)01300-9
In vivo activity:
The pyridine-methanol derivative Pirmenol hydrochloride is a new antiarrhythmic agent. Single-dose studies in rodents demonstrate a 10- to 15-fold difference between the po and iv LD50 values. In rats, the po LD50 is 359.9 mg/kg and the iv LD50 is 23.6 mg/kg. Mice LD50 values are 215.5 and 20.8 mg/kg for po and iv routes, respectively. Short-term subacute iv toxicity studies in rats (2.5, 5.0, and 7.5 mg/kg) and dogs (2.5, 5, and 10 mg/kg) for 4 weeks elicite minimal reactions. Cardiac effects in dogs include drug related increases in heart rate, increases QRS duration, shortening of ST interval without evidence of cardiac tissue damage and mild local reaction at the injection site. Orally, Pirmenol is well tolerated for 13 weeks in rats receiving 25, 50, and 100 mg/kg/day while dogs given 5, 10, and 15 mg/kg/day shows anticholinergic effects at high levels (dryness of mucosae, body tremors). Heart rates are significantly accelerated only at the beginning of the study and QRS changes are seen with wide individual variations. No drug-related tissue changes are elicited in these species. Teratology studies in rats (50, 100, and 150 mg/kg) and in rabbits (10, 25, and 50 mg/kg) show no overt effect on organogenesis but embryotoxicity is seen at 150 mg/kg in rats. Reference: Toxicol Appl Pharmacol. 1980 Nov;56(2):294-301. https://www.sciencedirect.com/science/article/pii/0041008X80903014?via%3Dihub
Solvent mg/mL mM comments
Solubility
DMSO 5.0 14.80
Ethanol 10.0 29.50
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 338.50 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:
In vitro protocol:
1. Watanabe Y, Hara Y, Tamagawa M, Nakaya H. Pirmenol inhibits muscarinic acetylcholine receptor-operated K+ current in the guinea pig heart. Eur J Pharmacol. 1997 Oct 29;338(1):71-4. doi: 10.1016/s0014-2999(97)01300-9. PMID: 9408005.
In vivo protocol:
1. Schardein JL, Fitzgerald JE, Sanyer JL, McGuire EJ, de la Iglesia FA. Preclinical toxicology studies with a new antiarrhythmic agent: pirmenol hydrochloride (CI-845). Toxicol Appl Pharmacol. 1980 Nov;56(2):294-301. doi: 10.1016/0041-008x(80)90301-4. PMID: 7466828.
1: Yonemizu S, Masuda K, Kurata Y, Notsu T, Higashi Y, Fukumura K, Li P, Ninomiya H, Miake J, Tsuneto M, Shirayoshi Y, Hisatome I. Inhibitory effects of class I antiarrhythmic agents on Na+ and Ca2+ currents of human iPS cell-derived cardiomyocytes. Regen Ther. 2019 Feb 1;10:104-111. doi: 10.1016/j.reth.2018.12.002. PMID: 30766898; PMCID: PMC6360514. 2: Martí-Carvajal AJ, Simancas-Racines D, Anand V, Bangdiwala S. Prophylactic lidocaine for myocardial infarction. Cochrane Database Syst Rev. 2015 Aug 21;2015(8):CD008553. doi: 10.1002/14651858.CD008553.pub2. PMID: 26295202; PMCID: PMC8454263. 3: Takahashi N, Ooie T, Nakagawa M, Hara M, Saikawa T, Yoshimatsu H. Progressive facilitation of antegrade conduction via an accessory pathway in a patient with Wolff-Parkinson-White syndrome and permanent atrial fibrillation. Intern Med. 2005 Dec;44(12):1264-8. doi: 10.2169/internalmedicine.44.1264. PMID: 16415547. 4: Mizuguchi Y, Ishimoto T, Kageyama N, Oishi Y, Emi S, Nagase N, Oki T. A patient responding to combined therapy with pirmenol and midodrine for refractory neurally mediated syncope complicated by prostatic hypertrophy. Cardiovasc Drugs Ther. 2004 Sep;18(5):405-8. doi: 10.1007/s10557-005-5066-8. PMID: 15717144. 5: Takada M, Goto T, Kotake T, Saito M, Kawato N, Nakai M, Gunji T, Shibakawa M. Appropriate dosing of antiarrhythmic drugs in Japan requires therapeutic drug monitoring. J Clin Pharm Ther. 2005 Feb;30(1):5-12. doi: 10.1111/j.1365-2710.2004.00612.x. PMID: 15658999. 6: Varró A, Biliczki P, Iost N, Virág L, Hála O, Kovács P, Mátyus P, Papp JG. Theoretical possibilities for the development of novel antiarrhythmic drugs. Curr Med Chem. 2004 Jan;11(1):1-11. doi: 10.2174/0929867043456296. PMID: 14754422. 7: Asano J, Kojima M, Sekizawa Y, Ooe T, Miyamoto N, Suzuki Y, Kohya T, Kobayashi M, Saitoh H. [An approach to complete the manual for determination of serum pirmenol levels]. Yakugaku Zasshi. 2003 Nov;123(11):981-6. Japanese. doi: 10.1248/yakushi.123.981. PMID: 14631760. 8: Kamiyama N, Koyama Y, Suetsuna R, Saito Y, Kaji S, Akasaka T, Yoshida K. Decreased left atrial appendage flow velocity with atrial fibrillation caused by negative inotropic agents: report of two cases. Circ J. 2003 Mar;67(3):277-8. doi: 10.1253/circj.67.277. PMID: 12604883. 9: Sutovsky I, Katoh T, Takayama H, Ono T, Takano T. Therapeutic monitoring of class I antiarrhythmic agents using high-resolution electrocardiography instead of blood samples. Circ J. 2003 Mar;67(3):195-8. doi: 10.1253/circj.67.195. PMID: 12604865. 10: Izawa A, Yazaki Y, Hayashi S, Imamura H, Kusama Y, Isobe M. Transient left ventricular aneurysm and hypertrophy accompanied by polymorphic ventricular tachycardia in a patient suspected of acute myocarditis. Jpn Heart J. 2000 Jan;41(1):97-102. doi: 10.1536/jhj.41.97. PMID: 10807534. 11: Yamamoto N, Ozaki T, Keida Y, Ohtsuka M, Goto T. A comparison of the binding characteristics of class I antiarrhythmic agents for human muscarinic m1-m3 receptors. J Cardiovasc Pharmacol. 1999 Jul;34(1):53-9. doi: 10.1097/00005344-199907000-00009. PMID: 10413067. 12: Kasai H, Ueno K, Kusumoto M, Shibakawa M. Population pharmacokinetic analysis of pirmenol in healthy volunteers and patients with arrhythmia. Eur J Clin Pharmacol. 1999 Mar;55(1):77-8. doi: 10.1007/s002280050596. PMID: 10206089. 13: Kodama I, Ogawa S, Inoue H, Kasanuki H, Kato T, Mitamura H, Hiraoka M, Sugimoto T. Profiles of aprindine, cibenzoline, pilsicainide and pirmenol in the framework of the Sicilian Gambit. The Guideline Committee for Clinical Use of Antiarrhythmic Drugs in Japan (Working Group of Arrhythmias of the Japanese Society of Electrocardiology). Jpn Circ J. 1999 Jan;63(1):1-12. doi: 10.1253/jcj.63.1. PMID: 10084381. 14: Abe H, Numata T, Hanada H, Kohshi K, Nakashima Y. Pirmenol hydrochloride- induced QT prolongation and T wave inversion on electrocardiogram during treatment for symptomatic atrial fibrillation. J UOEH. 1998 Dec 1;20(4):339-43. doi: 10.7888/juoeh.20.339. PMID: 9883483. 15: Nakajima T, Iwasawa K, Hazama H, Omata M. Effects of pirmenol on action potentials and membrane currents in single atrial myocytes. Eur J Pharmacol. 1998 Mar 5;344(2-3):287-97. doi: 10.1016/s0014-2999(97)01579-3. PMID: 9600665. 16: Nakagomi M, Suzuki E, Kitashima M, Iida S, Abe M, Matsuki Y, Kaneko K. Sex difference in the metabolism of pirmenol in rats. Biol Pharm Bull. 1997 Dec;20(12):1279-84. doi: 10.1248/bpb.20.1279. PMID: 9448104. 17: Watanabe Y, Hara Y, Tamagawa M, Nakaya H. Pirmenol inhibits muscarinic acetylcholine receptor-operated K+ current in the guinea pig heart. Eur J Pharmacol. 1997 Oct 29;338(1):71-4. doi: 10.1016/s0014-2999(97)01300-9. PMID: 9408005. 18: Janiczek N, Smith DE, Chang T, Sedman AJ, Stringer KA. Pharmacokinetics of pirmenol enantiomers and pharmacodynamics of pirmenol racemate in patients with premature ventricular contractions. J Clin Pharmacol. 1997 Jun;37(6):502-13. doi: 10.1002/j.1552-4604.1997.tb04328.x. PMID: 9208357. 19: Janiczek N, Smith DE, Chang T, Ventura A, Mertz TE. Pharmacokinetics and pharmacodynamics of pirmenol enantiomers in coronary artery ligated dogs. J Pharm Sci. 1997 Apr;86(4):443-9. doi: 10.1021/js960369f. PMID: 9109046. 20: Atarashi H, Kuruma A, Ino T, Hirayama Y, Saitoh H, Hayakawa H. Clinical effects and pharmacokinetics of a single oral dose of pirmenol hydrochloride. J Cardiovasc Pharmacol. 1996 Apr;27(4):556-62. doi: 10.1097/00005344-199604000-00015. PMID: 8847873.