5-Methoxy-N,N-diisopropyltryptamine

Identification

Name
5-Methoxy-N,N-diisopropyltryptamine
Accession Number
DB01441
Type
Small Molecule
Groups
Experimental, 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
  • 5-MeO-DIPT
  • 5-methoxy-N,N-bis(1-methylethyl)-1H-Indole-3-ethanamine
  • Foxy
  • Foxy methoxy
Categories
UNII
12D06G8W8E
CAS number
4021-34-5
Weight
Average: 274.4011
Monoisotopic: 274.204513464
Chemical Formula
C17H26N2O
InChI Key
DNBPMBJFRRVTSJ-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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics

5-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 action
Not Available
Absorption

5-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 distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
151182
PubChem Substance
46506676
ChemSpider
133247
ChEBI
48282
ChEMBL
CHEMBL2140942
Wikipedia
5-Methoxy-diisopropyltryptamine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)181 °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 RuleNoChemAxon
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 inhibitorNon-inhibitor0.8466
CYP450 2D6 inhibitorInhibitor0.6223
CYP450 2C19 inhibitorNon-inhibitor0.8076
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as tryptamines and derivatives. These are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Tryptamines and derivatives
Direct Parent
Tryptamines and derivatives
Alternative Parents
3-alkylindoles / Alkaloids and derivatives / Anisoles / Aralkylamines / Alkyl aryl ethers / Substituted pyrroles / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds
show 1 more
Substituents
Tryptamine / 3-alkylindole / Indole / Alkaloid or derivatives / Anisole / Alkyl aryl ether / Aralkylamine / Benzenoid / Substituted pyrrole / Heteroaromatic compound
show 13 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tryptamines (CHEBI:48282)

Drug created on July 31, 2007 07:09 / Updated on December 01, 2017 14:43