NAV

5-Methoxy-N,N-diisopropyltryptamine

Identification

Generic Name
5-Methoxy-N,N-diisopropyltryptamine
DrugBank Accession Number
DB01441
Background

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.

Type
Small Molecule
Groups
Experimental, Illicit
Structure
3D
Similar Structures
Weight
Average: 274.4011
Monoisotopic: 274.204513464
Chemical Formula
C17H26N2O
Synonyms
  • 5-MeO-DIPT
  • 5-methoxy-N,N-bis(1-methylethyl)-1H-indole-3-ethanamine
  • Foxy
  • Foxy methoxy
  • N-(1-methylethyl)-N-{2-[5-(methyloxy)-1H-indol-3-yl]ethyl}propan-2-amine
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
3-alkylindole / Alkaloid or derivatives / Alkyl aryl ether / Amine / Anisole / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Ether
show 13 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
tryptamines (CHEBI:48282)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
12D06G8W8E
CAS number
4021-34-5
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

References

General References
Not Available
PubChem Compound
151182
PubChem Substance
46506676
ChemSpider
133247
ChEBI
48282
ChEMBL
CHEMBL2140942
ZINC
ZINC000002583773
Wikipedia
5-Methoxy-diisopropyltryptamine

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

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-MSsplash10-01vo-9550000000-9ccc6b8146967b3f342e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00b9-0590000000-0dcd2d0a3328d8b6c3e0
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00dl-0090000000-75a6e64873dc12ed2a4e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-2950000000-11869d14023aa2c1ef25
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00si-1390000000-94cf6d5e37f4808beeb4
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00al-0900000000-374db0daa8a06dcc986b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-052g-0920000000-e06aed023e954c4d568d
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-175.8091252
predicted
DarkChem Lite v0.1.0
[M-H]-169.56468
predicted
DeepCCS 1.0 (2019)
[M+H]+176.7136252
predicted
DarkChem Lite v0.1.0
[M+H]+171.92268
predicted
DeepCCS 1.0 (2019)
[M+Na]+176.3926252
predicted
DarkChem Lite v0.1.0
[M+Na]+178.01582
predicted
DeepCCS 1.0 (2019)

Drug created at July 31, 2007 13:09 / Updated at June 12, 2020 16:51