Synonym
Alifedrine; Alifedrine HCl; D 13625; D-13625; D13625
IUPAC/Chemical Name
1-cyclohexyl-3-(((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)amino)propan-1-one hydrochloride
InChi Key
AKEXDXACYGXMJG-DJKAKHFESA-N
InChi Code
InChI=1S/C18H27NO2.ClH/c1-14(18(21)16-10-6-3-7-11-16)19-13-12-17(20)15-8-4-2-5-9-15;/h3,6-7,10-11,14-15,18-19,21H,2,4-5,8-9,12-13H2,1H3;1H/t14-,18-;/m0./s1
SMILES Code
O=C(C1CCCCC1)CCN[C@@H](C)[C@H](O)C2=CC=CC=C2.[H]Cl
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
Biological target:
Alifedrine, also known as D13625, is a positive inotropic agent.
In vivo activity:
Acute ischemic left ventricular failure was induced in dogs by coronary embolization with plastic microspheres, resulting in reduced cardiac output (CO), increased left ventricular end-diastolic pressure (LVEDP), pulmonary capillary pressure (PCP), and total peripheral resistance (TPR). Intravenous (i.v.) administration of alifedrine, a beta-adrenergic partial agonist (0.3 mg/kg as bolus and 0.3 mg/kg/h as infusion), significantly improved performance of the failing heart. Thus, alifedrine in this model markedly improved left ventricular function by balanced stimulation of the myocardium and reduction of pre- and afterload.
Reference: J Cardiovasc Pharmacol. 1989 Jul;14(1):103-8. https://pubmed.ncbi.nlm.nih.gov/2475700/
Preparing Stock Solutions
The following data is based on the
product
molecular weight
325.88
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.
| 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. Metzenauer P, Dedecke R, Göbel H, Martorana PA, Stroman F, Szelenyi I. Effects of the novel beta-adrenergic partial agonist alifedrine on cardiac performance in dogs with acute ischemic left ventricular failure. J Cardiovasc Pharmacol. 1989 Jul;14(1):103-8. doi: 10.1097/00005344-198907000-00018. PMID: 2475700.
2. Wainwright CL, Parratt JR. Alifedrine, a positive inotropic agent that moderately reduces the severity of ischaemia and reperfusion-induced ventricular arrhythmias. Eur J Pharmacol. 1988 Mar 15;147(3):373-80. doi: 10.1016/0014-2999(88)90171-9. PMID: 3378563.
In vivo protocol:
1. Metzenauer P, Dedecke R, Göbel H, Martorana PA, Stroman F, Szelenyi I. Effects of the novel beta-adrenergic partial agonist alifedrine on cardiac performance in dogs with acute ischemic left ventricular failure. J Cardiovasc Pharmacol. 1989 Jul;14(1):103-8. doi: 10.1097/00005344-198907000-00018. PMID: 2475700.
2. Wainwright CL, Parratt JR. Alifedrine, a positive inotropic agent that moderately reduces the severity of ischaemia and reperfusion-induced ventricular arrhythmias. Eur J Pharmacol. 1988 Mar 15;147(3):373-80. doi: 10.1016/0014-2999(88)90171-9. PMID: 3378563.
1: Anand IS, Hughes LO, Whittington JR, Raftery EB. Acute haemodynamic effects of different doses of alifedrine in congestive heart failure. Eur J Clin Pharmacol. 1989;36(4):335-41. PubMed PMID: 2737225.
2: Wan SK, Hoff W, Evans TR. Haemodynamic effects of intravenous and oral alifedrine in patients with cardiac failure. Curr Med Res Opin. 1988;11(4):242-53. PubMed PMID: 3215041.
3: Schanzenbächer P, Riegger G, Liebau G, Hockerts T, Kochsiek K. [Acute hemodynamic effects of alifedrine in patients with heart failure]. Z Kardiol. 1984 Feb;73(2):95-100. German. PubMed PMID: 6719988.
4: Wainwright CL, Parratt JR. Alifedrine, a positive inotropic agent that moderately reduces the severity of ischaemia and reperfusion-induced ventricular arrhythmias. Eur J Pharmacol. 1988 Mar 15;147(3):373-80. PubMed PMID: 3378563.
5: Metzenauer P, Dedecke R, Göbel H, Martorana PA, Stroman F, Szelenyi I. Effects of the novel beta-adrenergic partial agonist alifedrine on cardiac performance in dogs with acute ischemic left ventricular failure. J Cardiovasc Pharmacol. 1989 Jul;14(1):103-8. PubMed PMID: 2475700.
6: Engel J, Bekel H, Heiliger D, Schaumlöffel E. [14C-labeling of alifedrine hydrochloride, a new positive inotropic compound]. Arch Pharm (Weinheim). 1985 May;318(5):465-7. German. PubMed PMID: 4026541.
7: Bickel E, Engel J, Klingler KH. [Syntheses of 14C-1-erythro-norephedrine and its N-substitution products 14C-oxyfedrine and 14C-D 13,625]. Arzneimittelforschung. 1983;33(9):1213-5. German. PubMed PMID: 6685500.
8: Colucci WS, Wright RF, Braunwald E. New positive inotropic agents in the treatment of congestive heart failure. Mechanisms of action and recent clinical developments. 2. N Engl J Med. 1986 Feb 6;314(6):349-58. Review. PubMed PMID: 2418353.
