(1S,2S)-2-amino-1-phenylpropan-1-ol

• ChemBase ID: 1282
• Molecular Formular: C9H13NO
• Molecular Mass: 151.20562
• Monoisotopic Mass: 151.09971404
• SMILES: O[C@H]([C@@H](N)C)c1ccccc1
• Canonical SMILES: O[C@@H](c1ccccc1)[C@@H](N)C
• InChI: InChI=1S/C9H13NO/c1-7(10)9(11)8-5-3-2-4-6-8/h2-7,9,11H,10H2,1H3/t7-,9+/m0/s1
• InChIKey: DLNKOYKMWOXYQA-IONNQARKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S)-2-amino-1-phenylpropan-1-ol
• IUPAC Traditional name: cathine
• Synonyms: (+)-Cathine; (+)-Pseudonorephedrine; (1S,2S)-2-Amino-1-phenyl-1-propanol; D-(+)-Norpseudoephedrine; (1S,2S)-(+)-Norpseudoephedrine; β-hydroxyamphetamine; D-Cathine; (+)-Norpseudoephedrine; norpseudoephedrine; (+)-norephedrin; (1S,2R)-(+)-Norephedrine; D-norephedrine; D-phenylpropanolamine; Katine; Pseudonorephedrine; Cathine; (+)-去甲伪麻黄碱; (+)-阿茶碱; (1S,2S)-2-氨基-1-苯基-1-丙醇; D-(+)-去甲伪麻黄碱; (1S,2S)-(+)-去甲伪麻黄碱

Database IDs

• CAS Number: 492-39-7
• EC Number: 207-754-1
• MDL Number: MFCD01711268
• PubChem SID: 46509110; 160964742
• PubChem CID: 441457
• ATC CODE: A08AA07
• Chemspider ID: 390189
• DrugBank ID: DB01486
• Unique Ingredient Identifier: E1L4ZW2F8O
• Wikipedia Title: Cathine

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.896164
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -2.0889428
• LogD (pH = 7.4): -1.0537072
• Log P: 0.8852543
• Molar Refractivity: 44.9127 cm^3
• Polarizability: 18.00672 Å^3
• Polar Surface Area: 46.25 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 0.57
• LOG S: -0.87
• Solubility (Water): 2.06e+01 g/l

PROPERTIES

Physical Property

• Solubility: 20 mg/mL at 25 oC [BEILSTEIN]
• Optical Rotation: [α]/D +34.0±2.0°, c = 3.5 in ethanol
• Hydrophobicity(logP): 0.83 [SANGSTER (1994)]

Safety Information

• RTECS: RC9100000
• European Hazard Symbols: Harmful (Xn)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H319-H335
• GHS Precautionary statements: P261-P301 + P310-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• RID/ADR: UN 2811 6.1/PG 3
• Drug Control: USDEA Schedule IV; regulated under CDSA - not available from Sigma-Aldrich Canada
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: Oral
• Half Life: 3 hours
• Legal Status: POM (UK); Rx-only; Schedule IV (US)
• Pregnancy Category: C

Product Information

• Purity: ≥98.0% (NT)

DETAILS

DrugBank - DB01486

• Drug Groups: illicit; experimental
• Description: Cathine (β-hydroxyamphetamine) is a monoamine alkaloid found in the shrub Catha edulis (khat). Cathine is a Schedule III drug under the Convention on Psychotropic Substances. In the United States, it is classified as a Schedule IV controlled substance. [Wikipedia]
• Indication: Used to decrease appetite.
• Pharmacology: Closely related to ephedrine, cathinone and other amphetamines, it may contribute to the stimulant effect of Catha edulis, although another constituent, cathinone appears to show stronger activity.
• Affected Organisms: Humans and other mammals
• Absorption: The mucosa of the oral cavity is considered to be the first absorption segment, where the major proportion of the alkaloids is absorbed (mean +/- SD: 84 +/- 6% for cathine). [PMID: 12848785]
• Half Life: 5.2 +/- 3.4 hours
• References: Toennes SW, Harder S, Schramm M, Niess C, Kauert GF: Pharmacokinetics of cathinone, cathine and norephedrine after the chewing of khat leaves. Br J Clin Pharmacol. 2003 Jul;56(1):125-30. [Pubmed]
• External Links: Wikipedia

Sigma Aldrich - 689661

Packaging
1, 5 g in glass bottle
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 689661.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

REFERENCES

• Toennes SW, Harder S, Schramm M, Niess C, Kauert GF: Pharmacokinetics of cathinone, cathine and norephedrine after the chewing of khat leaves. Br J Clin Pharmacol. 2003 Jul;56(1):125-30. Pubmed