| Identification | Back Directory | [Name]
Gepefrine | [CAS]
18840-47-6 | [Synonyms]
Gepefrine
Gepefrine [inn]
Unii-V51rrx51vh
(S)-3-(2-AMINOPROPYL)PHENOL
Phenol, 3-[(2S)-2-aminopropyl]- | [Molecular Formula]
C9H13NO | [MOL File]
18840-47-6.mol | [Molecular Weight]
151.21 |
| Chemical Properties | Back Directory | [Melting point ]
155-158° | [alpha ]
D25 +31.8° (c = 2 in methanol) | [Boiling point ]
281.0±15.0 °C(Predicted) | [density ]
1.070±0.06 g/cm3(Predicted) | [pka]
9.86±0.10(Predicted) | [InChI]
InChI=1S/C9H13NO/c1-7(10)5-8-3-2-4-9(11)6-8/h2-4,6-7,11H,5,10H2,1H3/t7-/m0/s1 | [InChIKey]
WTDGMHYYGNJEKQ-ZETCQYMHSA-N | [SMILES]
C1(O)=CC=CC(C[C@@H](N)C)=C1 |
| Hazard Information | Back Directory | [Originator]
Pressionorm,Helopharm,W. Germany,1981 | [Uses]
Gepefrine is an orally active pressor agent and sympathomimetic agent. Gepefrine improves the early orthostatic disregulation of the arterial pressure[1][2][3]. | [Manufacturing Process]
Hydrolysis of D-(+)-1-(3-rnethoxyphenyl)-2-aminopropane: 2.42 mols (40 g)
of the compound are dissolved in 6N hydrochloric acid in a bomb tube
consisting of stainless steel and having a capacity of 500 ml. Hydrogen
chloride gas is passed into the ice-cooled solution until this is saturated, The
solution is then heated to 130°C for 2 hours in an air bath. After cooling and
driving off the hydrochloric acid at a slightly elevated temperature, the
hydrochloride of the 3-hydroxyphenyl derivative is present in the form of a
yellowish syrup.
The free base can be liberated from the hydrochloride by extracting a butanol
solution of the hydrochloride several times with sodium bicarbonate solution.
After recrystallization from isopropanol/ligroin, the yield of D-(+)-1-(3-
hydroxyphenyl)-2-aminopropane amounts to 33.0 g, corresponding to 90.1%
of theory relative to the D-form. Melting point = 152°C to 154°C. | [Therapeutic Function]
Antihypotensive | [References]
[1] Peters FT, et al. Drug testing in blood: validated negative-ion chemical ionization gas chromatographic-mass spectrometric assay for determination of amphetamine and methamphetamine enantiomers and its application to toxicology cases. Clin Chem. 2002 Sep;48(9):1472-85. PMID:12194924
[2] Lossnitzer K, et al. Vergleichende Untersuchungen antihypotensiv wirksamer Sympathikomimetika im Kipptisch-Versuch [Therapy of orthostatic dysregulation. Comparative studies on anti-hypotensive sympathomimetics with a tilt-table test]. Fortschr Med. 1980 Aug 7;98(29):(1133-6). German. PMID:6108908
[3] Bachour G, et al. [Therapy of orthostatic dysregulation with gepefrin. Study with continuous telemetric blood pressure monitoring]. Z Kardiol. 1985 Apr;74(4):228-33. German. PMID:4002776 |
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Leancare Ltd.
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+33 962096793 |
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www.leancare.co.uk |
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