CAS 492-39-7|(+)-norephedrin|(1S,2S)-2-amino-1-phenylpropan-1-ol|cathine|Katine|norpseudoephedrine|β-hydroxyamphetamine|Cathine|D-Cathine|D-norephedrine|D-phenylpropanolamine|(1S,2R)-(+)-Norephedri...

General Information

Structure

Molecular Formula

C₉H₁₃NO

Molecular Mass

151.20562

Exact Mass

151.09971404

Charge

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

Canonic Smiles

O[C@@H](c1ccccc1)[C@@H](N)C

Isomeric Smiles

O[C@H]([C@@H](N)C)c1ccccc1

Calculated Properties

JChem

LogD (pH = 7.4)

-0.92

LogD (pH = 5.5)

-2.07

Log P

0.89

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

9.22

Polar Surface Area

46.25

Polarizability

16.88

Molar Refractivity

44.91

LOG S

-1.32

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Synonyms

D-norephedrine(+)-NorpseudoephedrinePseudonorephedrineKatinenorpseudoephedrine(1S,2R)-(+)-NorephedrineCathine(+)-norephedrinβ-hydroxyamphetamineD-CathineD-phenylpropanolamine(+)-阿茶碱(1S,2S)-(+)-NorpseudoephedrineD-(+)-Norpseudoephedrine(+)-Cathine(+)-去甲伪麻黄碱D-(+)-去甲伪麻黄碱(1S,2S)-2-氨基-1-苯基-1-丙醇(1S,2S)-2-Amino-1-phenyl-1-propanol(+)-Pseudonorephedrine(1S,2S)-(+)-去甲伪麻黄碱cathine(1S,2S)-2-amino-1-phenyl-1-propanolD-cathineD-norpseudoephedrine(+)-cathine(1S,2S)-(+)-norpseudoephedrined-norpseudoephedrine(+)-norpseudoephedrinekatine(+)-pseudonorephedrine(1S,2S)-norpseudoephedrineD-(+)-norpseudoephedrine

IUPAC name

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

IUPAC Traditional name

cathine

Names and Identifiers

Registration numbers

MDL Number

MFCD01711268

CAS Number

492-39-7

PubChem SID

16096474246509110223439434

EC Number

PubChem CID

Chemspider ID

ATC CODE

DrugBank ID

Unique Ingredient Identifier

E1L4ZW2F8O

Wikipedia Title

Cathine

PubMed Citation Links

36624923014845034464621335518123482112934040530362158328873376664457715513978325897653341404831721333317798023960776333706551715821325013783

CHEMBL

KNApSAcK Database

KEGG ID

Reaxys Registry

SureChEMBL Database

BindingDB Database

MetaboLights Database

MTBLS4463MTBLS1693

Drug Central Database

KEGG DRUG Database

CHEBI ID

CompTox Database

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

0.83 [SANGSTER (1994)]

Solubility

20 mg/mL at 25 oC [BEILSTEIN]

Optical Rotation

[α]/D +34.0±2.0°, c = 3.5 in ethanol

Product Information

Purity

≥98.0% (NT)

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule 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]

Wikipedia

Cathine

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.

ChEBI

CHEBI:4109

An amphetamine that is propylbenzene substituted by a hydroxy group at position 1 and by an amino group at position 2 (the 1S,2S-stereoisomer).

Molecule Details

References

PubChem Literature

From Data Sources

• 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

References

Bioactivity

PubChem BioAssay

Bioactivity

Data Source

Academic Data

Commercial Catalog

Names and Identifiers

Synonyms

IUPAC name

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

IUPAC Traditional name

cathine

Registration numbers

MDL Number

MFCD01711268

CAS Number

492-39-7

PubChem SID

16096474246509110223439434

EC Number

PubChem CID

Chemspider ID

ATC CODE

DrugBank ID

Unique Ingredient Identifier

E1L4ZW2F8O

Wikipedia Title

Cathine

PubMed Citation Links

36624923014845034464621335518123482112934040530362158328873376664457715513978325897653341404831721333317798023960776333706551715821325013783

CHEMBL

KNApSAcK Database

KEGG ID

Reaxys Registry

SureChEMBL Database

BindingDB Database

MetaboLights Database

MTBLS4463MTBLS1693

Drug Central Database

KEGG DRUG Database

CHEBI ID

CompTox Database

Molecule Details

DB01486

Drug Groups

illicit; experimental

Description

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]

Cathine

689661

An amphetamine that is propylbenzene substituted by a hydroxy group at position 1 and by an amino group at position 2 (the 1S,2S-stereoisomer).

References

PubChem Literature

From Data Sources

• 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

Bioactivity

PubChem BioAssay

Properties

Physical Property

Hydrophobicity(logP)

0.83 [SANGSTER (1994)]

Solubility

20 mg/mL at 25 oC [BEILSTEIN]

Optical Rotation

[α]/D +34.0±2.0°, c = 3.5 in ethanol

Product Information

Purity

≥98.0% (NT)

Molecule

ID:1282