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MedKoo Cat#: 341378 | Name: Prenylamine
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Description:

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

Prenylamine is a calcium channel blocker of the amphetamine chemical class which was used as a vasodilator in the treatment of angina pectoris.

Chemical Structure

Prenylamine
CAS#390-64-7

Theoretical Analysis

MedKoo Cat#: 341378

Name: Prenylamine

CAS#: 390-64-7

Chemical Formula: C24H27N

Exact Mass: 329.2143

Molecular Weight: 329.49

Elemental Analysis: C, 87.49; H, 8.26; N, 4.25

Price and Availability

Size Price Availability Quantity
10mg USD 450.00
50mg USD 800.00
100mg USD 1,300.00
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Related CAS #
No Data
Synonym
Prenylamine; SAN 13-194; SAN-13-194; SAN13-194.
IUPAC/Chemical Name
Benzenepropanamine, N-(1-methyl-2-phenylethyl)-gamma-phenyl-
InChi Key
IFFPICMESYHZPQ-UHFFFAOYSA-N
InChi Code
InChI=1S/C24H27N/c1-20(19-21-11-5-2-6-12-21)25-18-17-24(22-13-7-3-8-14-22)23-15-9-4-10-16-23/h2-16,20,24-25H,17-19H2,1H3
SMILES Code
CC(NCCC(C1=CC=CC=C1)C2=CC=CC=C2)CC3=CC=CC=C3
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
>3 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
2934.99.03.00
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Prenylamine is a calcium channel blocker of the amphetamine chemical class which was used as a vasodilator in the treatment of angina pectoris.
In vitro activity:
This study characterizes the tonic and use-dependent block of prenylamine on wild-type human cardiac voltage-gated sodium channels (hNav1.5) transiently expressed in human embryonic kidney 293t cells under whole-cell voltage-clamp condition. Prenylamine exhibits tonic block at both hyperpolarizing and depolarizing potentials on hNav1.5 channels with 50% inhibitory concentrations of 9.67 +/- 0.25 microM and 0.72 +/- 0.02 microM, respectively. Substitutions of the amino acids at the putative local anesthetic binding site (i.e., F1760, N1765, Y1767, and N406) with lysine had much lesser effects on prenylamine block of the mutant hNav1.5 channels compared with local anesthetic block. The affinity of prenylamine was reduced at most by 5.8-fold, whereas that of bupivacaine, a known local anesthetic, was reduced by as much as 68-fold compared with wild-type by the mutations at the local anesthetic receptor site. Reference: Mol Pharmacol. 2002 Aug;62(2):415-22. https://pubmed.ncbi.nlm.nih.gov/12130695/
In vivo activity:
The authors characterized the tonic and use-dependent prenylamine block of native Na(+) channels in cultured rat neuronal GH3 cells during whole cell voltage clamp conditions and the local anesthetic effect of prenylamine by neurologic evaluation of sensory and motor functions of sciatic nerve during neural block in rats. In vivo data show that 10 mm prenylamine produced a complete sciatic nerve block of motor function, proprioceptive responses, and nociceptive responses that lasted approximately 27, 34, and 24 h, respectively. Rats injected with 15.4 mm bupivacaine, a known local anesthetic currently used for pain management, had a significantly shorter duration of blockade (< 2 h) compared with rats injected with prenylamine. Reference: Anesthesiology. 2001 Nov;95(5):1198-204. https://pubmed.ncbi.nlm.nih.gov/11684990/

Preparing Stock Solutions

The following data is based on the product molecular weight 329.49 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. Mujtaba MG, Wang SY, Wang GK. Prenylamine block of Nav1.5 channel is mediated via a receptor distinct from that of local anesthetics. Mol Pharmacol. 2002 Aug;62(2):415-22. doi: 10.1124/mol.62.2.415. PMID: 12130695. 2. Popper LD, Batra SC. Release of intracellular calcium by prenylamine in human ovarian tumour cells. Cancer Lett. 1993 Jul 30;71(1-3):5-10. doi: 10.1016/0304-3835(93)90089-r. PMID: 8364898. 3. Mujtaba MG, Gerner P, Wang GK. Local anesthetic properties of prenylamine. Anesthesiology. 2001 Nov;95(5):1198-204. doi: 10.1097/00000542-200111000-00025. PMID: 11684990.
In vitro protocol:
1. Mujtaba MG, Wang SY, Wang GK. Prenylamine block of Nav1.5 channel is mediated via a receptor distinct from that of local anesthetics. Mol Pharmacol. 2002 Aug;62(2):415-22. doi: 10.1124/mol.62.2.415. PMID: 12130695. 2. Popper LD, Batra SC. Release of intracellular calcium by prenylamine in human ovarian tumour cells. Cancer Lett. 1993 Jul 30;71(1-3):5-10. doi: 10.1016/0304-3835(93)90089-r. PMID: 8364898.
In vivo protocol:
1. Mujtaba MG, Gerner P, Wang GK. Local anesthetic properties of prenylamine. Anesthesiology. 2001 Nov;95(5):1198-204. doi: 10.1097/00000542-200111000-00025. PMID: 11684990.
1: Huang T, He J, Zhou X, Pan H, He F, Du A, Yu B, Jiang N, Li X, Yuan K, Wang Z. Discovering common pathogenetic processes between COVID-19 and tuberculosis by bioinformatics and system biology approach. Front Cell Infect Microbiol. 2023 Dec 15;13:1280223. doi: 10.3389/fcimb.2023.1280223. PMID: 38162574; PMCID: PMC10757339. 2: Chen G, Che L, Cai X, Zhu P, Ran J. Bioinformatic Analysis Identifies Biomarkers and Treatment Targets in Primary Sjögren's Syndrome Patients with Fatigue. Biomed Res Int. 2022 Jan 15;2022:7697558. doi: 10.1155/2022/7697558. PMID: 35075430; PMCID: PMC8783724. 3: Joseph A, Kumar GJ, Pawar SD, Hirlekar BU, Bharatam PV, Konda S, Mudiam MKR, Murty US, Sahu PL, Dubey S, Radhakrishnanand P, Adye DR, Borkar RM, Thirupathi C, Kumar P. Analytical developments of p-hydroxy prenylamine reference material for dope control research: Characterization and purity assessment. Drug Test Anal. 2022 Feb;14(2):224-232. doi: 10.1002/dta.3171. Epub 2021 Oct 26. PMID: 34617411. 4: Shah RR, Stonier PD. Withdrawal of prenylamine: perspectives on pharmacological, clinical and regulatory outcomes following the first QT-related casualty. Ther Adv Drug Saf. 2018 Jun 18;9(8):475-493. doi: 10.1177/2042098618780854. PMID: 30364900; PMCID: PMC6199680. 5: Abdel-Qadir H, Ong G, Fazelzad R, Amir E, Lee DS, Thavendiranathan P, Tomlinson G. Interventions for preventing cardiomyopathy due to anthracyclines: a Bayesian network meta-analysis. Ann Oncol. 2017 Mar 1;28(3):628-633. doi: 10.1093/annonc/mdw671. PMID: 28028033. 6: Wang J, Li M, Wang Y, Liu X. Integrating subpathway analysis to identify candidate agents for hepatocellular carcinoma. Onco Targets Ther. 2016 Mar 7;9:1221-30. doi: 10.2147/OTT.S97211. PMID: 27022281; PMCID: PMC4788366. 7: St-Onge M, Dubé PA, Gosselin S, Guimont C, Godwin J, Archambault PM, Chauny JM, Frenette AJ, Darveau M, Le Sage N, Poitras J, Provencher J, Juurlink DN, Blais R. Treatment for calcium channel blocker poisoning: a systematic review. Clin Toxicol (Phila). 2014 Nov;52(9):926-44. doi: 10.3109/15563650.2014.965827. Epub 2014 Oct 6. PMID: 25283255; PMCID: PMC4245158. 8: Raphemot R, Kadakia RJ, Olsen ML, Banerjee S, Days E, Smith SS, Weaver CD, Denton JS. Development and validation of fluorescence-based and automated patch clamp-based functional assays for the inward rectifier potassium channel Kir4.1. Assay Drug Dev Technol. 2013 Nov-Dec;11(9-10):532-43. doi: 10.1089/adt.2013.544. Epub 2013 Nov 22. PMID: 24266659; PMCID: PMC3870600. 9: Beuck S, Sigmund G, Koch A, Schänzer W, Pokrywka A, Kwiatkowska D, Thevis M. Identification and characterization of urinary prenylamine metabolites by means of liquid chromatography-tandem mass spectrometry. Drug Test Anal. 2012 Sep;4(9):701-16. doi: 10.1002/dta.1388. Epub 2012 Jul 12. PMID: 22786790. 10: Amobi N, Guillebaud J, Smith IC. Contractile actions of L-type Ca2+ agonists in human vas deferens and effects of structurally different Ca2+ antagonists. Eur J Pharmacol. 2010 Feb 10;627(1-3):285-94. doi: 10.1016/j.ejphar.2009.10.043. Epub 2009 Oct 28. PMID: 19878664. 11: Lohmann A, Schöttler MA, Bréhélin C, Kessler F, Bock R, Cahoon EB, Dörmann P. Deficiency in phylloquinone (vitamin K1) methylation affects prenyl quinone distribution, photosystem I abundance, and anthocyanin accumulation in the Arabidopsis AtmenG mutant. J Biol Chem. 2006 Dec 29;281(52):40461-72. doi: 10.1074/jbc.M609412200. Epub 2006 Nov 2. PMID: 17082184. 12: Katchman AN, Koerner J, Tosaka T, Woosley RL, Ebert SN. Comparative evaluation of HERG currents and QT intervals following challenge with suspected torsadogenic and nontorsadogenic drugs. J Pharmacol Exp Ther. 2006 Mar;316(3):1098-106. doi: 10.1124/jpet.105.093393. Epub 2005 Nov 8. PMID: 16278312. 13: Molinari A, Oliva A, Ojeda C, Miguel del Corral JM, Castro MA, Cuevas C, San Feliciano A. New cytotoxic-antineoplastic prenyl-1,2-naphthohydroquinone derivatives. Bioorg Med Chem. 2005 Dec 15;13(24):6645-50. doi: 10.1016/j.bmc.2005.07.042. Epub 2005 Sep 16. PMID: 16169232. 14: Mathieu F, Galmier MJ, Pognat JF, Lartigue C. Influence of different calcic antagonists on the Caco-2 cell monolayer integrity or "TEER, a measurement of toxicity?". Eur J Drug Metab Pharmacokinet. 2005 Jan-Jun;30(1-2):85-90. doi: 10.1007/BF03226412. PMID: 16010866. 15: Escoubet S, Gastaldi S, Timokhin VI, Bertrand MP, Siri D. Thiyl radical- mediated cleavage of allylic C-N bonds: scope, limitations, and theoretical support to the mechanism. J Am Chem Soc. 2004 Oct 6;126(39):12343-52. doi: 10.1021/ja049859x. PMID: 15453768. 16: Elizarov SM, Gavrilina AV, Danilenko VN. Modulirovanie aktivnosti serin- treonin-proteinkinaz u khloramfenikol-ustoĭchivykh mutantov Streptomyces avermitilis [Modulation of serine/threonine protein kinase activity in chloramphenicol-resistant mutants of Streptomyces avermitilis]. Mol Biol (Mosk). 2004 May-Jun;38(3):394-403. Russian. PMID: 15285607. 17: Urwyler S, Gjoni T, Kaupmann K, Pozza MF, Mosbacher J. Selected amino acids, dipeptides and arylalkylamine derivatives do not act as allosteric modulators at GABAB receptors. Eur J Pharmacol. 2004 Jan 12;483(2-3):147-53. doi: 10.1016/j.ejphar.2003.10.024. PMID: 14729102. 18: Okada M, Hatakeyama T, Itoh H, Tokuta N, Tokumitsu H, Kobayashi R. S100A1 is a novel molecular chaperone and a member of the Hsp70/Hsp90 multichaperone complex. J Biol Chem. 2004 Feb 6;279(6):4221-33. doi: 10.1074/jbc.M309014200. Epub 2003 Nov 24. PMID: 14638689. 19: Kraemer T, Roditis SK, Peters FT, Maurer HH. Amphetamine concentrations in human urine following single-dose administration of the calcium antagonist prenylamine-studies using fluorescence polarization immunoassay (FPIA) and GC- MS. J Anal Toxicol. 2003 Mar;27(2):68-73. doi: 10.1093/jat/27.2.68. PMID: 12669999. 20: Kerr DI, Ong J, Puspawati NM, Prager RH. Arylalkylamines are a novel class of positive allosteric modulators at GABA(B) receptors in rat neocortex. Eur J Pharmacol. 2002 Sep 6;451(1):69-77. doi: 10.1016/s0014-2999(02)02195-7. PMID: 12223231.

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