You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
Identification
NameTrans-2-Phenylcyclopropylamine
Accession NumberDB02665  (EXPT03088)
TypeSmall Molecule
GroupsExperimental
Description

A propylamine formed from the cyclization of the side chain of amphetamine. This monoamine oxidase inhibitor is effective in the treatment of major depression, dysthymic disorder, and atypical depression. It also is useful in panic and phobic disorders. (From AMA Drug Evaluations Annual, 1994, p311)

Structure
Thumb
SynonymsNot Available
External Identifiers 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
SaltsNot Available
Categories
UNIINot Available
CAS numberNot Available
WeightAverage: 134.1983
Monoisotopic: 134.096974389
Chemical FormulaC9H12N
InChI KeyInChIKey=AELCINSCMGFISI-DTWKUNHWSA-O
InChI
InChI=1S/C9H11N/c10-9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6,10H2/p+1/t8-,9+/m0/s1
IUPAC Name
(1R,2S)-2-phenylcyclopropan-1-aminium
SMILES
[NH3+][C@@H]1C[[email protected]]1C1=CC=CC=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds
Super ClassOrganonitrogen compounds
ClassAmines
Sub ClassAralkylamines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Quaternary ammonium salt
  • Hydrocarbon derivative
  • Organic cation
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9819
Blood Brain Barrier+0.9453
Caco-2 permeable+0.7871
P-glycoprotein substrateNon-substrate0.8338
P-glycoprotein inhibitor INon-inhibitor0.9558
P-glycoprotein inhibitor IINon-inhibitor0.9827
Renal organic cation transporterNon-inhibitor0.8684
CYP450 2C9 substrateNon-substrate0.7997
CYP450 2D6 substrateNon-substrate0.8768
CYP450 3A4 substrateNon-substrate0.7287
CYP450 1A2 substrateInhibitor0.8593
CYP450 2C9 inhibitorNon-inhibitor0.8734
CYP450 2D6 inhibitorNon-inhibitor0.6988
CYP450 2C19 inhibitorInhibitor0.8154
CYP450 3A4 inhibitorNon-inhibitor0.9587
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6521
Ames testNon AMES toxic0.9213
CarcinogenicityNon-carcinogens0.721
BiodegradationReady biodegradable0.8237
Rat acute toxicity2.4558 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9604
hERG inhibition (predictor II)Non-inhibitor0.9333
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0104 mg/mLALOGPS
logP-1.6ALOGPS
logP1.34ChemAxon
logS-4.2ALOGPS
pKa (Strongest Basic)9.62ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area27.64 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity52.99 m3·mol-1ChemAxon
Polarizability15.83 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Vithal Jagannath Rajadhyaksha, “Method of synthesis of trans-2-phenylcyclopropylamine.” U.S. Patent US4016204, issued October, 1964.

US4016204
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB Entries
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Serine-type endopeptidase activity
Specific Function:
Has activity against the synthetic substrates Boc-Phe-Ser-Arg-Mec, Boc-Leu-Thr-Arg-Mec, Boc-Gln-Ala-Arg-Mec and Boc-Val-Pro-Arg-Mec. The single-chain form is more active than the two-chain form against all of these substrates.
Gene Name:
PRSS1
Uniprot ID:
P07477
Molecular Weight:
26557.88 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Comments
comments powered by Disqus
Drug created on June 13, 2005 07:24 / Updated on August 17, 2016 12:23