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Identification
NameCathine
Accession NumberDB01486
Typesmall molecule
Groupsexperimental, illicit
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]

Structure
Thumb
Synonyms
SynonymLanguageCode
(+)-norephedrinNot AvailableNot Available
(+)-NorpseudoephedrineNot AvailableNot Available
(1S,2R)-(+)-NorephedrineNot AvailableNot Available
D-CathineNot AvailableNot Available
D-norephedrineNot AvailableNot Available
D-phenylpropanolamineNot AvailableNot Available
KatineNot AvailableNot Available
norpseudoephedrineNot AvailableNot Available
PseudonorephedrineNot AvailableNot Available
β-hydroxyamphetamineNot AvailableNot Available
SaltsNot Available
Brand namesNot Available
Brand mixturesNot Available
Categories
CAS number492-39-7
WeightAverage: 151.2056
Monoisotopic: 151.099714043
Chemical FormulaC9H13NO
InChI KeyDLNKOYKMWOXYQA-IONNQARKSA-N
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
IUPAC Name
(1S,2S)-2-amino-1-phenylpropan-1-ol
SMILES
C[C@H](N)[C@@H](O)C1=CC=CC=C1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenethylamines
Direct parentAmphetamines and Derivatives
Alternative parentsSecondary Alcohols; 1,2-Aminoalcohols; Polyamines; Monoalkylamines
Substituents1,2-aminoalcohol; secondary alcohol; polyamine; primary amine; amine; primary aliphatic amine; alcohol; organonitrogen compound
Classification descriptionThis compound belongs to the amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
Pharmacology
IndicationUsed to decrease appetite.
PharmacodynamicsClosely 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.
Mechanism of actionNot Available
AbsorptionThe 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]
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half life5.2 +/- 3.4 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9871
Blood Brain Barrier + 0.5843
Caco-2 permeable + 0.7568
P-glycoprotein substrate Non-substrate 0.7276
P-glycoprotein inhibitor I Non-inhibitor 0.9849
P-glycoprotein inhibitor II Non-inhibitor 0.9917
Renal organic cation transporter Non-inhibitor 0.9113
CYP450 2C9 substrate Non-substrate 0.8077
CYP450 2D6 substrate Non-substrate 0.8418
CYP450 3A4 substrate Non-substrate 0.8063
CYP450 1A2 substrate Non-inhibitor 0.9046
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.9231
CYP450 2C19 substrate Non-inhibitor 0.9026
CYP450 3A4 substrate Non-inhibitor 0.9261
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9096
Ames test Non AMES toxic 0.9132
Carcinogenicity Non-carcinogens 0.6929
Biodegradation Not ready biodegradable 0.6917
Rat acute toxicity 2.0244 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9446
hERG inhibition (predictor II) Non-inhibitor 0.937
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point77.5-78 °CNot Available
water solubility2E+004 mg/L (at 25 °C)BEILSTEIN
logP0.83SANGSTER (1994)
Predicted Properties
PropertyValueSource
water solubility2.06e+01 g/lALOGPS
logP0.57ALOGPS
logP0.89ChemAxon
logS-0.87ALOGPS
pKa (strongest acidic)13.9ChemAxon
pKa (strongest basic)9.37ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count2ChemAxon
polar surface area46.25ChemAxon
rotatable bond count2ChemAxon
refractivity44.91ChemAxon
polarizability16.87ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Shawn R. Hitchcock, Jonathan Andrew Groeper, “Method of preparing pseudonorephedrine.” U.S. Patent US07465830, issued December 16, 2008.

US07465830
General Reference
  1. 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
ResourceLink
KEGG CompoundC08300
PubChem Compound441457
PubChem Substance46509110
ChemSpider390189
WikipediaCathine
ATC CodesA08AA07
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
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Drug created on July 31, 2007 07:09 / Updated on September 16, 2013 17:14