Identification
NameCathine
Accession NumberDB01486
TypeSmall Molecule
GroupsExperimental, Illicit
Description

Cathine, also known as d-norpseudoephedrine and (+)-norpseudoephedrine, is a psychoactive drug of the phenethylamine and amphetamine chemical classes which acts as a stimulant. In the United States, it is classified as a Schedule IV controlled substance.

Structure
Thumb
Synonyms
(+)-norephedrin
(+)-Norpseudoephedrine
(1S,2R)-(+)-Norephedrine
D-Cathine
D-norephedrine
D-phenylpropanolamine
Katine
norpseudoephedrine
Pseudonorephedrine
External IDs Not Available
Product Ingredients Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
Categories
UNIIE1L4ZW2F8O
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[[email protected]](N)[C@@H](O)C1=CC=CC=C1
Pharmacology
Indication

Used to decrease appetite.

Structured Indications Not Available
Pharmacodynamics

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.

Mechanism of actionNot Available
Related Articles
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]

Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half life

5.2 +/- 3.4 hours

ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions Not Available
Food InteractionsNot Available
References
Synthesis Reference

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

US07465830
General References
  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:12848785 ]
External Links
ATC CodesA08AA07 — Cathine
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)77.5-78 °CNot Available
water solubility2E+004 mg/L (at 25 °C)BEILSTEIN
logP0.83SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility20.6 mg/mLALOGPS
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 Area46.25 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity44.91 m3·mol-1ChemAxon
Polarizability16.87 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9871
Blood Brain Barrier+0.5843
Caco-2 permeable+0.7568
P-glycoprotein substrateNon-substrate0.7276
P-glycoprotein inhibitor INon-inhibitor0.9849
P-glycoprotein inhibitor IINon-inhibitor0.9917
Renal organic cation transporterNon-inhibitor0.9113
CYP450 2C9 substrateNon-substrate0.8077
CYP450 2D6 substrateNon-substrate0.8418
CYP450 3A4 substrateNon-substrate0.8063
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.9261
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9096
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.6929
BiodegradationNot ready biodegradable0.6917
Rat acute toxicity2.0244 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9446
hERG inhibition (predictor II)Non-inhibitor0.937
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as phenylpropanes. These are organic compounds containing a phenylpropane moiety.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentPhenylpropanes
Alternative ParentsAralkylamines / Secondary alcohols / 1,2-aminoalcohols / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives / Aromatic alcohols
SubstituentsPhenylpropane / Aralkylamine / 1,2-aminoalcohol / Secondary alcohol / Organic nitrogen compound / Hydrocarbon derivative / Aromatic alcohol / Organopnictogen compound / Primary amine / Organic oxygen compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptorsamphetamines (CHEBI:4109 ) / Phenylalanine derived alkaloids (C08300 )
Drug created on July 31, 2007 07:09 / Updated on July 18, 2017 16:59