4-Methyl-2,5-dimethoxyamphetamine

Identification

Generic Name
4-Methyl-2,5-dimethoxyamphetamine
DrugBank Accession Number
DB01528
Background

A psychedelic phenyl isopropylamine derivative, commonly called DOM, whose mood-altering effects and mechanism of action may be similar to those of LSD.

Type
Small Molecule
Groups
Experimental, Illicit
Structure
Weight
Average: 209.2848
Monoisotopic: 209.141578857
Chemical Formula
C12H19NO2
Synonyms
  • STP
External IDs
  • J401.288G

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

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
Not Available

Interactions

Drug Interactions
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

Products

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Product Ingredients
IngredientUNIICASInChI Key
2,5-dimethoxy-4-methylamphetamine hydrochlorideS7Q374AHPJ15589-00-1IPIMRNFGYPQKAM-UHFFFAOYSA-N

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenethylamines
Direct Parent
Amphetamines and derivatives
Alternative Parents
Dimethoxybenzenes / Phenylpropanes / Phenoxy compounds / Anisoles / Toluenes / Aralkylamines / Alkyl aryl ethers / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives
Substituents
Alkyl aryl ether / Amine / Amphetamine or derivatives / Anisole / Aralkylamine / Aromatic homomonocyclic compound / Dimethoxybenzene / Ether / Hydrocarbon derivative / Methoxybenzene
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
UKI9MLD5OI
CAS number
15588-95-1
InChI Key
NTJQREUGJKIARY-UHFFFAOYSA-N
InChI
InChI=1S/C12H19NO2/c1-8-5-12(15-4)10(6-9(2)13)7-11(8)14-3/h5,7,9H,6,13H2,1-4H3
IUPAC Name
1-(2,5-dimethoxy-4-methylphenyl)propan-2-amine
SMILES
COC1=CC(CC(C)N)=C(OC)C=C1C

References

General References
Not Available
PubChem Compound
85875
PubChem Substance
46504804
ChemSpider
77462
BindingDB
50005265
ChEMBL
CHEMBL8600
Guide to Pharmacology
GtP Drug Page

Clinical Trials

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Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP2.24HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.969 mg/mLALOGPS
logP2.02ALOGPS
logP2Chemaxon
logS-2.3ALOGPS
pKa (Strongest Basic)9.94Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area44.48 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity61.67 m3·mol-1Chemaxon
Polarizability24.09 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9971
Blood Brain Barrier+0.9322
Caco-2 permeable+0.7724
P-glycoprotein substrateNon-substrate0.7072
P-glycoprotein inhibitor INon-inhibitor0.8304
P-glycoprotein inhibitor IINon-inhibitor0.9609
Renal organic cation transporterNon-inhibitor0.8061
CYP450 2C9 substrateNon-substrate0.8379
CYP450 2D6 substrateSubstrate0.8345
CYP450 3A4 substrateNon-substrate0.5068
CYP450 1A2 substrateInhibitor0.6292
CYP450 2C9 inhibitorNon-inhibitor0.9714
CYP450 2D6 inhibitorInhibitor0.8316
CYP450 2C19 inhibitorNon-inhibitor0.8919
CYP450 3A4 inhibitorNon-inhibitor0.9071
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7422
Ames testNon AMES toxic0.6302
CarcinogenicityNon-carcinogens0.7951
BiodegradationNot ready biodegradable0.8606
Rat acute toxicity3.0267 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8845
hERG inhibition (predictor II)Non-inhibitor0.6909
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-MSsplash10-0006-6900000000-776d7576e097d8efa08b
GC-MS Spectrum - EI-BGC-MSsplash10-0006-9100000000-466e6b5613c401a0fa96
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ox-0930000000-d51320df30f1607a00c0
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0690000000-e0f362c7743aac7605f3
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03dl-1960000000-d2b33124865b66fc8684
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0930000000-cb3170e69cb6fa1211a9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00ll-1900000000-7537af69c73fbe871c1d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-0900000000-f447aa917c7160d33dcb
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]-147.44978
predicted
DeepCCS 1.0 (2019)
[M+H]+149.80779
predicted
DeepCCS 1.0 (2019)
[M+Na]+156.93651
predicted
DeepCCS 1.0 (2019)

Drug created at July 31, 2007 13:10 / Updated at June 12, 2020 16:51