Record Information
Version1.0
Created at2020-03-19 00:46:32 UTC
Updated at2020-12-07 19:07:35 UTC
CannabisDB IDCDB000610
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameFurfurylmethylamphetamine
DescriptionFurfurylmethylamphetamine or Furfenorex, belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine. It is an anorexic drug used in the treatment of obesity (PMID: 2874966 ). One of its metabolites was methamphetamine and has been withdrawn from the market due to abuse potential (PMID: 12024689 ). It is also a stimulant, which enhances the central nervous system activity by mimicking the action of brain neurotransmitters and, due to the ability to increase awareness and counteract fatigue, is misused by athletes participating in sports that require high levels of physical and mental endurances (DOI: 10.1002/9781118533956). Furfurylmethylamphetamine has also been detected as a volatile component in cannabis plant samples obtained from police seizures (PMID: 26657499 ).
Structure
Thumb
SynonymsNot Available
Chemical FormulaC15H19NO
Average Molecular Weight229.32
Monoisotopic Molecular Weight229.1467
IUPAC Name[(furan-2-yl)methyl](methyl)[(2S)-1-phenylpropan-2-yl]amine
Traditional Name(furan-2-ylmethyl)(methyl)[(2S)-1-phenylpropan-2-yl]amine
CAS Registry Number3776-93-0
SMILES
C[C@@H](CC1=CC=CC=C1)N(C)CC1=CC=CO1
InChI Identifier
InChI=1S/C15H19NO/c1-13(11-14-7-4-3-5-8-14)16(2)12-15-9-6-10-17-15/h3-10,13H,11-12H2,1-2H3/t13-/m0/s1
InChI KeyDLGIIZAHQPTVCJ-ZDUSSCGKSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentAmphetamines and derivatives
Alternative Parents
Substituents
  • Amphetamine or derivatives
  • Phenylpropane
  • Aralkylamine
  • Furan
  • Heteroaromatic compound
  • Tertiary amine
  • Tertiary aliphatic amine
  • Organoheterocyclic compound
  • Oxacycle
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP3.61ALOGPS
logP3.4ChemAxon
logS-3.6ALOGPS
pKa (Strongest Basic)8.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area16.38 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity70.78 m³·mol⁻¹ChemAxon
Polarizability25.63 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available2020-06-30View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available2020-06-30View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID31046444
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound71777433
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Harris LS: The stimulants and hallucinogens under consideration: a brief overview of their chemistry and pharmacology. Drug Alcohol Depend. 1986 Jun;17(2-3):107-18. doi: 10.1016/0376-8716(86)90002-5. [PubMed:2874966 ]
  2. Cody JT: Precursor medications as a source of methamphetamine and/or amphetamine positive drug testing results. J Occup Environ Med. 2002 May;44(5):435-50. doi: 10.1097/00043764-200205000-00012. [PubMed:12024689 ]
  3. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]