This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
2,5-Dimethoxy-4-ethylthioamphetamine
DrugBank Accession Number
DB13940
Background

2,5-Dimethoxy-4-ethylthioamphetamine (ALEPH-2) is a phenylisopropylamine derivative with alleged anxiolytic and hallucinogenic properties.

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 255.38
Monoisotopic: 255.129300094
Chemical Formula
C13H21NO2S
Synonyms
  • 2,5-Dimethoxy-4-ethylthioamphetamine
  • 4-(Ethylthio)-2,5-dimethoxy-alpha-methylbenzeneethanamine
  • ALEPH-2

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
U5-hydroxytryptamine receptor 2A
agonist
Humans
U5-hydroxytryptamine receptor 2C
agonist
Humans
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
Adverseeffects
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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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when 1,2-Benzodiazepine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
AbaloparatideThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with Abaloparatide.
AcebutololThe therapeutic efficacy of Acebutolol can be decreased when used in combination with 2,5-Dimethoxy-4-ethylthioamphetamine.
AceclofenacThe risk or severity of hypertension can be increased when Aceclofenac is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
AcemetacinThe risk or severity of hypertension can be increased when Acemetacin is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
AcenocoumarolThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with Acenocoumarol.
AcetazolamideAcetazolamide may decrease the excretion rate of 2,5-Dimethoxy-4-ethylthioamphetamine which could result in a higher serum level.
AcetophenazineAcetophenazine may decrease the stimulatory activities of 2,5-Dimethoxy-4-ethylthioamphetamine.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
Aclidinium2,5-Dimethoxy-4-ethylthioamphetamine may increase the central nervous system depressant (CNS depressant) activities of Aclidinium.
Interactions
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Food Interactions
Not Available

Categories

Drug Categories
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 / Thiophenol ethers / Phenoxy compounds / Anisoles / Aralkylamines / Alkylarylthioethers / Alkyl aryl ethers / Sulfenyl compounds / Monoalkylamines
show 1 more
Substituents
Alkyl aryl ether / Alkylarylthioether / Amine / Amphetamine or derivatives / Anisole / Aralkylamine / Aromatic homomonocyclic compound / Aryl thioether / Dimethoxybenzene / Ether
show 16 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Z1I419DRZZ
CAS number
185562-00-9
InChI Key
MCYCODJKXUJSAT-UHFFFAOYSA-N
InChI
InChI=1S/C13H21NO2S/c1-5-17-13-8-11(15-3)10(6-9(2)14)7-12(13)16-4/h7-9H,5-6,14H2,1-4H3
IUPAC Name
1-[4-(ethylsulfanyl)-2,5-dimethoxyphenyl]propan-2-amine
SMILES
CCSC1=CC(OC)=C(CC(C)N)C=C1OC

References

General References
Not Available
ChemSpider
8439835
BindingDB
50164337
ChEMBL
CHEMBL339611

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

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

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.267 mg/mLALOGPS
logP2.9ALOGPS
logP2.37ChemAxon
logS-3ALOGPS
pKa (Strongest Basic)9.91ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area44.48 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity74.19 m3·mol-1ChemAxon
Polarizability29.15 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

Drugtargets2
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Virus receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodop...
Gene Name
HTR2A
Uniprot ID
P28223
Uniprot Name
5-hydroxytryptamine receptor 2A
Molecular Weight
52602.58 Da
References
  1. Acuna-Castillo C, Scorza C, Reyes-Parada M, Cassels BK, Huidobro-Toro JP: ALEPH-2, a suspected anxiolytic and putative hallucinogenic phenylisopropylamine derivative, is a 5-HT2a and 5-HT2c receptor agonist. Life Sci. 2000 Nov 17;67(26):3241-7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
Serotonin receptor activity
Specific Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-...
Gene Name
HTR2C
Uniprot ID
P28335
Uniprot Name
5-hydroxytryptamine receptor 2C
Molecular Weight
51820.705 Da
References
  1. Acuna-Castillo C, Scorza C, Reyes-Parada M, Cassels BK, Huidobro-Toro JP: ALEPH-2, a suspected anxiolytic and putative hallucinogenic phenylisopropylamine derivative, is a 5-HT2a and 5-HT2c receptor agonist. Life Sci. 2000 Nov 17;67(26):3241-7. [Article]

Drug created at January 01, 2018 03:29 / Updated at June 12, 2020 16:53