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Norephedrine

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Identification
Molecular formula
C9H13NO
CAS number
14838-15-4
IUPAC name
(1R,2S)-2-amino-1-phenyl-propan-1-ol
State
State

At room temperature, norephedrine is a solid. It is a stable compound under normal conditions of use and storage.

Melting point (Celsius)
173.00
Melting point (Kelvin)
446.15
Boiling point (Celsius)
285.00
Boiling point (Kelvin)
558.15
General information
Molecular weight
151.21g/mol
Molar mass
151.2060g/mol
Density
1.0810g/cm3
Appearence

Norephedrine appears as a white to off-white solid. It is typically found in crystalline form and is often available as a powder. The compound is known for its purity and consistency in texture.

Comment on solubility

Solubility of (1R,2S)-2-amino-1-phenyl-propan-1-ol

(1R,2S)-2-amino-1-phenyl-propan-1-ol, commonly referred to as a chiral amino alcohol, exhibits notable solubility characteristics due to its functional groups. Its solubility can generally be characterized as follows:

  • Water Solubility: This compound tends to be soluble in water, primarily because of the presence of the amino group (-NH2), which can form hydrogen bonds with water molecules.
  • Polar Solvents: It is likely to dissolve well in polar organic solvents such as methanol and ethanol, enhancing its utility in various chemical applications.
  • Non-Polar Solvents: Conversely, it is expected to show limited solubility in non-polar solvents like hexane, due to the insufficient interaction between the molecule and the solvent.

In conclusion, the solubility of (1R,2S)-2-amino-1-phenyl-propan-1-ol can be summarized as:

  1. Good solubility in water and polar solvents.
  2. Poor solubility in non-polar solvents.

This solubility profile is attributed to the compound's functional groups, making it an interesting subject for study in pharmaceutical and biochemical contexts. As you consider its potential applications, remember that "like dissolves like," which emphasizes the importance of polarity in predicting solubility behavior.

Interesting facts

Interesting Facts about (1R,2S)-2-amino-1-phenyl-propan-1-ol

(1R,2S)-2-amino-1-phenyl-propan-1-ol is a fascinating chemical compound primarily noted for its role in medicinal chemistry and its chiral properties. Here are some intriguing points to consider:

  • Chirality: This compound is a chiral molecule, meaning it exists in two enantiomeric forms. Chirality is crucial in pharmaceuticals because often only one of the enantiomers has the desired therapeutic effect, while the other may be less effective or even harmful.
  • Medicinal Applications: (1R,2S)-2-amino-1-phenyl-propan-1-ol is related to several biologically active compounds, making it a valuable scaffold in drug discovery. It is particularly important for the development of central nervous system agents and other therapeutic drugs.
  • Mechanism of Action: The presence of the amino group in this compound allows it to participate in various biochemical reactions, making it a key ingredient in synthesizing more complex natural products.
  • Study of Stereochemistry: It provides an interesting case study in stereochemistry, demonstrating how slight variations in molecular structure can lead to significant differences in biological activity.
  • Analytical Techniques: The compound can be analyzed using various techniques, including NMR spectroscopy and chromatography, which help in confirming its stereochemistry and purity in research settings.

To quote a famous chemist, "The beauty of chemistry lies in its symmetry and complexity." This compound perfectly illustrates this beauty.

Moreover, the exploration of such compounds sparks discussions around chiral resolution, a technique used to separate the two enantiomers for research and medicinal purposes. The ongoing study of (1R,2S)-2-amino-1-phenyl-propan-1-ol not only enhances our understanding of organic chemistry but also enriches the pharmaceutical industry.

Synonyms
phenylpropanolamine
Propadrine
Rhindecon
Mucron
Super Odrinex
Phenylpropanolamina
Phenylpropanolaminum
Phenylfenesin
Rinexin
Fansia
Fenilpropanolamina
UNII-33RU150WUN
erythro-2-Amino-1-phenyl-1-propanol
33RU150WUN
dl-1-Phenyl-2-aminopropanol-1
HSDB 6485
NSC 9920
EINECS 211-850-9
EINECS 238-900-2
PPA [Nasal Decongestant]
dl-2-Amino-1-hydroxy-1-phenylpropane
Benzyl alcohol, alpha-(1-aminoethyl)-
BRN 3196918
Phenylpropanolaminum [INN-Latin]
Phenylpropanolamina [INN-Spanish]
4-13-00-01875 (Beilstein Handbook Reference)
NSC17704
(R*,S*)-(1)-alpha-(1-Aminoethyl)benzyl alcohol
Benzenemethanol, alpha-(1-aminoethyl)-, (R*,S*)-
Benzenemethanol, alpha-(1-aminoethyl)-, (R*,S*)-(+-)-
PPA (Nasal Decongestant)
Phenylpropanolaminum (INN-Latin)
Phenylpropanolamina (INN-Spanish)
PHENYLPROPANOLAMINE (MART.)
PHENYLPROPANOLAMINE [MART.]
NSC-9920
beta-hydroxyamphetamine
DTXSID4023466
Phenylpropanolamin
PPA(ChemID)
Phenylpropanolamine1534
DTXCID10820534
R01BA01
dl-1-Phenyl-2-aminopropanol-1(ChemID)
Benzyl alcohol, alpha-(1-aminoethyl)-(ChemID)
dl-2-Amino-1-hydroxy-1-phenylpropane(ChemID)
(R*,S*)-(+-)-alpha-(1-Aminoethyl)benzenemethanol
(R*,S*)-(1)-alpha-(1-Aminoethyl)benzyl alcohol(ChemID)
238-900-2
benzenemethanol, alpha-(1-aminoethyl)-, (r*,s*)-, (+-)
(-)-Norephedrine
l-Norephedrine
492-41-1
(-)-Norephedrin
Mydriatin
(1R,2S)-(-)-Norephedrine
l-Phenylpropanolamine
(1R,2S)-Norephedrine
L-(-)-Ephedrine
NOREPHEDRINE, (-)-
erythro-(1R,2S)-Norephedrine
USAF CS-6
(R,S)-(-)-Norephedrine
(1R,2S)-2-Amino-1-phenyl-1-propanol
(1R,2S)-2-amino-1-phenylpropan-1-ol
(+-)-Norephedrine
(+/-)-Norephedrine
(-)-Phenylpropanolamine
(+-)-Phenylpropanolamine
NSC 17704
14838-15-4
dl-Phenylpropanolamine
1-Propanol, 2-amino-1-phenyl-, (-)-
57B9YG5Y1E
CHEBI:80680
(1R,2S)-PHENYLPROPANOLAMINE
NSC-17704
(1R,2S)-(-)-Norephedrine, 99%
Benzyl alcohol,.alpha.-(1-aminoethyl)-
Phenylpropanolamine (INN)
(+/-)-Phenylpropanolamine
PHENYLPROPANOLAMINE [INN]
Benzenemethanol, .alpha.-((1S)-1-aminoethyl)-, (.alpha.R)-
Benzenemethanol, .alpha.-[(1S)-1-aminoethyl]-, (.alpha.R)-
Fenilpropanolamina [Italian]
(+-)-Norephedrin
SR-05000001534
EINECS 207-755-7
CHEMBL136560
Phenylpropanolamine (VAN)
UNII-57B9YG5Y1E
1-norephedrine
Phenylpropanolamine [INN:BAN]
Benzyl alcohol, alpha-(1-aminoethyl)-, (-)-
Fansia (TN)
1-(-)-ephedrine
dl-alpha-(1-Aminoethyl)benzyl alcohol
dl-alpha-Hydroxy-beta-aminopropylbenzene
Benzenemethanol, alpha-((1S)-1-aminoethyl)-, (alphaR)-
Benzenemethanol, alpha-(1-aminoethyl)-, (R-(R*,S*))-
Spectrum_001103
Spectrum2_000016
Spectrum3_000889
Spectrum4_000983
Spectrum5_001156
(1R,2S)- Norephedrine
Benzenemethanol, .alpha.-(1-aminoethyl)-, [R-(R*,S*)]-
WLN: ZY1&YQR -L
KBioGR_001385
KBioSS_001583
(R-(R*,S*))-alpha-(1-Aminoethyl)benzyl alcohol
SCHEMBL152038
(1s,2r)-2-hydroxy-2-phenyl-1-methyl-1-aminoethane
1S,2R-PHENYLPROPANOLAMINE HYDROCHLORIDE
SPBio_000051
PHENYLPROPANOLAMINE, L-
(1r, 2s)-(-)-norephedrine
PHENYLPROPANOLAMINE [MI]
KBio2_001583
KBio2_004151
KBio2_006719
KBio3_001778
DTXSID10889348
PHENYLPROPANOLAMINE [HSDB]
1-Propanol, 2-amino-1-phenyl-
(1R, 2S)-(-)- norephedrine
HMS2090P12
PHENYLPROPANOLAMINE [VANDF]
PHENYLPROPANOLAMINE, (-)-
(1R,2S)-(-)-Phenylpropanolamine
PHENYLPROPANOLAMINE [WHO-DD]
PDSP1_001349
PDSP2_001333
AKOS015891206
CCG-214826
DB00397
N0608
(1R,2S)-(-)-2-Amino-1-phenyl-1-propanol
C07911
D08368
AB01275538-01
SR-05000001534-1
SR-05000001534-2
(-)-ERYTHRO-2-AMINO-2-METHYL-1-PHENYLETHANOL
(R*,S*)-(+/-)-alpha-(1-Aminoethyl)benzenemethanol
Q26840801
SELEGILINE HYDROCHLORIDE IMPURITY C [EP IMPURITY]
Benzenemethanol, alpha-((1R)-1-aminoethyl)-, (alphaS)-rel-
BENZENEMETHANOL, alpha-(1-AMINOETHYL)-, (R*,S*)-, (+/-)
BENZENEMETHANOL, .ALPHA.-(1-AMINOETHYL)-, (R*,S*)-, (+/-)-
InChI=1/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9-/m0/s