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MedKoo Cat#: 329405 | Name: Ajmaline
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Description:

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

Ajmaline, also known as Gilurytmal and Ritmos, is a sodium channel blocker used to treat arrhythmia. Ajmaline is also often used to bring out typical findings of ST elevations in patients suspected of having Brugada syndrome.

Chemical Structure

Ajmaline
Ajmaline
CAS#4360-12-7 (free base)

Theoretical Analysis

MedKoo Cat#: 329405

Name: Ajmaline

CAS#: 4360-12-7 (free base)

Chemical Formula: C20H26N2O2

Exact Mass: 326.1994

Molecular Weight: 326.44

Elemental Analysis: C, 73.59; H, 8.03; N, 8.58; O, 9.80

Price and Availability

Size Price Availability Quantity
100mg USD 90.00 Ready to ship
250mg USD 180.00 Ready to ship
500mg USD 285.00 Ready to ship
1g USD 465.00 Ready to ship
2g USD 750.00 Ready to ship
5g USD 1,550.00 Ready to ship
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Related CAS #
4410-48-4 (HCl) 4360-12-7 (free base)
Synonym
(+)-Ajmaline; Cardiorythmine; Gilurytmal; Ignazin; Merabitol; NSC 15627; Raugalline; Rauwolfin; Rauwolfine; Rhytmaton; Ritmos; Rytmalin; Siddiqui; Tachmalin; Takycor;
IUPAC/Chemical Name
(5aR,6S,8S,9S,10R,11S,11aS,12aR,13R)-9-ethyl-5-methyl-5a,6,8,9,10,11,11a,12-octahydro-5H-6,10:11,12a-dimethanoindolo[3,2-b]quinolizine-8,13-diol
InChi Key
CJDRUOGAGYHKKD-KBPCXUENSA-N
InChi Code
InChI=1S/C20H26N2O2/c1-3-10-11-8-14-17-20(12-6-4-5-7-13(12)21(17)2)9-15(16(11)18(20)23)22(14)19(10)24/h4-7,10-11,14-19,23-24H,3,8-9H2,1-2H3/t10-,11-,14-,15-,16-,17-,18+,19-,20+/m0/s1
SMILES Code
CN1[C@]2([C@@]3(C[C@H]4[C@@H]([C@H](O)N3[C@@H]5[C@H]4[C@@H](O)[C@@]2(C6=C1C=CC=C6)C5)CC)[H])[H]
Appearance
White to off-white solid powder
Purity
>96% (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:
Ajmaline (Cardiorythmine) is a sodium channel blocking, class 1A anti-arrhythmic agent.
In vitro activity:
Following administration of ajmaline, this study observed marked inhibition of INa in hiPSC-CMs compared to baseline control (Fig. 3A, B), and this inhibition was partially recovered after washout: pA/pF control = -110 ± 18.7, ajmaline = -15.4 ± 4.4, washout = -55 ± 11.6. When isolating outward potassium currents, the perfusion of ajmaline at 100 μM also resulted in an approximate 50% reduction in current density and a complete disappearance of peak tail current density compared to baseline control, which could be partially recovered after washout (Fig. 3C–F). The complete loss of tail current indicates that ajmaline acts to completely block IKr at 100 μM. These data therefore show that ajmaline inhibits both sodium and potassium currents in hiPSC-CMs, and support our observation that ajmaline lengthens the activation-recovery interval of hiPSC cardiac clusters by inhibiting IKr. Reference: Stem Cell Res. 2017 Dec; 25: 233–244. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5727153/
In vivo activity:
Ajmaline effectively blocks not only voltage-gated Na+ currents but also K+ currents in frog skeletal muscle fibres. Interestingly, when comparing this ‘loose-patch’ data on IK blocking of ajmaline to those obtained under prolonged depolarizations using the 2-MVC technique, ajmaline seems to block early IK components with a higher potency than late steady-state IK after several 100 ms. In particular, 100 μM ajmaline showed clear effects, whereas for 25 μM of ajmaline effects on steady-state IK were much smaller. This lower concentration, however, already strongly reduced the early peak IK. This suggests differential affinities of ajmaline towards different Kv families expressed in skeletal muscle (see Figure 1a). Reference: Br J Pharmacol. 2007 May;151(1):82-93. https://bpspubs.onlinelibrary.wiley.com/doi/full/10.1038/sj.bjp.0707194
Solvent mg/mL mM
Solubility
DMSO 61.7 188.92
DMF 25.0 76.58
Ethanol 10.0 30.63
PBS (pH 7.2) 0.3 0.77
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 326.44 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. Miller DC, Harmer SC, Poliandri A, Nobles M, Edwards EC, Ware JS, Sharp TV, McKay TR, Dunkel L, Lambiase PD, Tinker A. Ajmaline blocks INa and IKr without eliciting differences between Brugada syndrome patient and control human pluripotent stem cell-derived cardiac clusters. Stem Cell Res. 2017 Dec;25:233-244. doi: 10.1016/j.scr.2017.11.003. Epub 2017 Nov 7. PMID: 29172153; PMCID: PMC5727153. 2. Friedrich O, V Wegner F, Wink M, Fink RH. NA+- and K+-channels as molecular targets of the alkaloid ajmaline in skeletal muscle fibres. Br J Pharmacol. 2007 May;151(1):82-93. doi: 10.1038/sj.bjp.0707194. Epub 2007 Mar 12. PMID: 17351660. 3. Bébarová M, Matejovic P, Pásek M, Simurdová M, Simurda J. Effect of ajmaline on action potential and ionic currents in rat ventricular myocytes. Gen Physiol Biophys. 2005 Sep;24(3):311-25. PMID: 16308426.
In vitro protocol:
1. Miller DC, Harmer SC, Poliandri A, Nobles M, Edwards EC, Ware JS, Sharp TV, McKay TR, Dunkel L, Lambiase PD, Tinker A. Ajmaline blocks INa and IKr without eliciting differences between Brugada syndrome patient and control human pluripotent stem cell-derived cardiac clusters. Stem Cell Res. 2017 Dec;25:233-244. doi: 10.1016/j.scr.2017.11.003. Epub 2017 Nov 7. PMID: 29172153; PMCID: PMC5727153.
In vivo protocol:
1. Friedrich O, V Wegner F, Wink M, Fink RH. NA+- and K+-channels as molecular targets of the alkaloid ajmaline in skeletal muscle fibres. Br J Pharmacol. 2007 May;151(1):82-93. doi: 10.1038/sj.bjp.0707194. Epub 2007 Mar 12. PMID: 17351660. 2. Bébarová M, Matejovic P, Pásek M, Simurdová M, Simurda J. Effect of ajmaline on action potential and ionic currents in rat ventricular myocytes. Gen Physiol Biophys. 2005 Sep;24(3):311-25. PMID: 16308426.
1: Rizzo A, Borio G, Sieira J, Van Dooren S, Overeinder I, Bala G, Pappaert G, Maj R, Osório TG, Terasawa M, Galli A, Cecchini F, Miraglia V, Ströker E, La Meir M, Brugada P, Chierchia GB, de Asmundis C. Ajmaline Testing and the Brugada Syndrome. Am J Cardiol. 2020 Nov 15;135:91-98. doi: 10.1016/j.amjcard.2020.08.024. Epub 2020 Aug 27. PMID: 32861732. 2: Said SM, Husser D, Bollmann A, Piorkowski C, Braun-Dullaeus RC. Ajmalin-Test [Ajmaline test]. Dtsch Med Wochenschr. 2010 Mar;135(11):513-5. German. doi: 10.1055/s-0030-1249197. Epub 2010 Mar 10. PMID: 20221967. 3: Lounasmaa M, Hanhinen P. The ajmaline group of indole alkaloids. Alkaloids Chem Biol. 2001;55:1-87. doi: 10.1016/s0099-9598(01)55002-6. PMID: 11704984. 4: Ilyas M. Ajmaline in the management of cardiac arrhythmias. J Pak Med Assoc. 1981 Jul;31(7):153-5. PMID: 6792399. 5: STERKOWICZ S. AJMALINA [AJMALINE]. Pol Tyg Lek. 1964 Sep 7;19:1381-2. Polish. PMID: 14224360. 6: Antzelevitch C, Patocskai B. Ajmaline-Induced Slowing of Conduction in the Right Ventricular Outflow Tract Cannot Account for ST Elevation in Patients With Type I Brugada ECG. Circ Arrhythm Electrophysiol. 2017 Oct;10(10):e005775. doi: 10.1161/CIRCEP.117.005775. PMID: 29038108; PMCID: PMC5685558. 7: Ozeke O, Aras D, Cay S, Ozcan F, Acar B, Topaloglu S. Ajmaline-induced Epsilon wave: Its role is not only for diagnosis but also for risk stratification. Int J Cardiol. 2018 Aug 1;264:99. doi: 10.1016/j.ijcard.2018.03.046. PMID: 29776580. 8: Belhassen B. Ajmaline-induced torsade de pointes. Cardiology. 1986;73(1):54-5. doi: 10.1159/000173982. PMID: 3948201. 9: Chen W, Ma Y, He W, Wu Y, Huang Y, Zhang Y, Tian H, Wei K, Yang X, Zhang H. Structure units oriented approach towards collective synthesis of sarpagine- ajmaline-koumine type alkaloids. Nat Commun. 2022 Feb 17;13(1):908. doi: 10.1038/s41467-022-28535-x. PMID: 35177620; PMCID: PMC8854706. 10: Brugada J, Brugada P, Brugada R. The ajmaline challenge in Brugada syndrome: a useful tool or misleading information? Eur Heart J. 2003 Jun;24(12):1085-6. doi: 10.1016/s0195-668x(03)00232-x. PMID: 12804922. 11: Roten L, Derval N, Sacher F, Pascale P, Wilton SB, Scherr D, Shah A, Pedersen ME, Jadidi AS, Miyazaki S, Knecht S, Hocini M, Jaïs P, Haïssaguerre M. Ajmaline attenuates electrocardiogram characteristics of inferolateral early repolarization. Heart Rhythm. 2012 Feb;9(2):232-9. doi: 10.1016/j.hrthm.2011.09.013. Epub 2011 Sep 10. PMID: 21914496. 12: Nault I, Champagne J. How safe is ajmaline challenge in patients with suspected Brugada syndrome? Heart Rhythm. 2013 Dec;10(12):1875-6. doi: 10.1016/j.hrthm.2013.10.047. Epub 2013 Oct 28. PMID: 24177371. 13: Viskin S, Rosso R. Read My Lips: A Positive Ajmaline Test Does Not Always Mean You Have Brugada Syndrome. JACC Clin Electrophysiol. 2017 Dec 11;3(12):1409-1411. doi: 10.1016/j.jacep.2017.05.016. Epub 2017 Aug 30. PMID: 29759672. 14: Köppel C, Tenczer J, Arndt I. Metabolic disposition of ajmaline. Eur J Drug Metab Pharmacokinet. 1989 Oct-Dec;14(4):309-16. doi: 10.1007/BF03190117. PMID: 2633926. 15: Belhassen B, Motté G. Ajmaline cardiotoxicity. Am J Cardiol. 1984 Oct 1;54(7):942. doi: 10.1016/s0002-9149(84)80273-8. PMID: 6486064. 16: NELEMANS FA. AJMALINE (GILURYTMAL) [AJMALINE (GILURYTMAL)]. Ned Tijdschr Geneeskd. 1964 Jul 18;108:1420-2. Dutch. PMID: 14178503. 17: Arnalsteen-Dassonvalle E, Hermida JS, Kubala M, Six I, Quenum S, Leborgne L, Jarry G. Ajmaline challenge for the diagnosis of Brugada syndrome: which protocol? Arch Cardiovasc Dis. 2010 Nov-Dec;103(11-12):570-8. doi: 10.1016/j.acvd.2010.10.007. Epub 2010 Nov 30. PMID: 21147441. 18: Martini B. The ajmaline challenge and a strange ECG. Europace. 2009 Oct;11(10):1406; author reply 1406-7. doi: 10.1093/europace/eup224. PMID: 19797154. 19: Fomina IG. Klinicheskoe primenenie aĭmalina [Clinical use of ajmaline]. Klin Med (Mosk). 1973 Nov;51(11):9-15. Russian. PMID: 4132418. 20: Obayashi K, Nagasawa K, Mandel WJ, Vyden JK, Parmley WW. Cardiovascular effects of ajmaline. Am Heart J. 1976 Oct;92(4):487-96. doi: 10.1016/s0002-8703(76)80049-x. PMID: 961588.

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