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Identification
Name5-Methoxy-N,N-diisopropyltryptamine
Accession NumberDB01441
TypeSmall Molecule
GroupsExperimental, Illicit
Description

5-methoxy-N,N-diisopropyltryptamine (5-MeO-DIPT) is a tryptamine derivative and shares many similarities with schedule I tryptamine hallucinogens such as alpha-ethyltryptamine, N,N-dimethyltryptamine, N,N-diethyltryptamine, bufotenine, psilocybin and psilocin. Since 1999, there has been a growing popularity of 5-MeO-DIPT among drug abusers. This substance is abused for its hallucinogenic effects.

Structure
Thumb
Synonyms
SynonymLanguageCode
5-MeO-DIPTNot AvailableNot Available
5-methoxy-N,N-bis(1-methylethyl)-1H-Indole-3-ethanamineNot AvailableNot Available
FoxyNot AvailableNot Available
Foxy methoxyNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number4021-34-5
WeightAverage: 274.4011
Monoisotopic: 274.204513464
Chemical FormulaC17H26N2O
InChI KeyDNBPMBJFRRVTSJ-UHFFFAOYSA-N
InChI
InChI=1S/C17H26N2O/c1-12(2)19(13(3)4)9-8-14-11-18-17-7-6-15(20-5)10-16(14)17/h6-7,10-13,18H,8-9H2,1-5H3
IUPAC Name
[2-(5-methoxy-1H-indol-3-yl)ethyl]bis(propan-2-yl)amine
SMILES
COC1=CC2=C(NC=C2CCN(C(C)C)C(C)C)C=C1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassNot Available
Sub ClassNot Available
Direct ParentAlkaloids and derivatives
Alternative Parents
Substituents
  • Bufotenine
  • Serotonin
  • Tryptamine
  • Alkaloid or derivatives
  • Hydroxyindole
  • Indole or derivatives
  • Indole
  • Anisole
  • Aralkylamine
  • Alkyl aryl ether
  • Benzenoid
  • Substituted pyrrole
  • Heteroaromatic compound
  • Pyrrole
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationNot Available
Pharmacodynamics5-methoxy-diisopropyltryptamine, also known as 5-methoxy-N,N-diisopropyltryptamine, 5-MeO-DiPT, foxy methoxy, or just foxy, is a tryptamine that is used recreationally as a psychedelic. 5-MeO-DiPT is orally active, and dosages between 6–20 mg are commonly reported. Many users note an unpleasant body load accompanies higher dosages. 5-MeO-DiPT is also taken by insufflation, or sometimes it is smoked or injected. Some users also report sound distortion, also noted with the related drug, DiPT.
Mechanism of actionNot Available
Absorption5-MeO-DIPT produces effects with an onset of 20 to 30 minutes and with peak effects occurring between 1 to 1.5 hours after administration.
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
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
PropertyValueProbability
Human Intestinal Absorption+0.9949
Blood Brain Barrier+0.9894
Caco-2 permeable+0.5884
P-glycoprotein substrateSubstrate0.5834
P-glycoprotein inhibitor INon-inhibitor0.8303
P-glycoprotein inhibitor IIInhibitor0.5672
Renal organic cation transporterInhibitor0.728
CYP450 2C9 substrateNon-substrate0.8044
CYP450 2D6 substrateSubstrate0.6287
CYP450 3A4 substrateSubstrate0.7088
CYP450 1A2 substrateInhibitor0.9102
CYP450 2C9 substrateNon-inhibitor0.8466
CYP450 2D6 substrateInhibitor0.6223
CYP450 2C19 substrateNon-inhibitor0.8076
CYP450 3A4 substrateNon-inhibitor0.8104
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6161
Ames testNon AMES toxic0.6779
CarcinogenicityNon-carcinogens0.9499
BiodegradationNot ready biodegradable0.9964
Rat acute toxicity2.6241 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8067
hERG inhibition (predictor II)Non-inhibitor0.5364
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point181 °CNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0673 mg/mLALOGPS
logP4.35ALOGPS
logP3.69ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)17.44ChemAxon
pKa (Strongest Basic)10.68ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.26 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity85.24 m3·mol-1ChemAxon
Polarizability33.06 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 ReferenceNot Available
General Reference
  1. DEA Link
External Links
ATC CodesNot Available
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