2,5-Dimethoxy-4-ethylthioamphetamine

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

Identification

Name
2,5-Dimethoxy-4-ethylthioamphetamine
Accession Number
DB13940
Type
Small Molecule
Groups
Experimental
Description

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

Structure
Thumb
Synonyms
  • 2,5-Dimethoxy-4-ethylthioamphetamine
  • 4-(Ethylthio)-2,5-dimethoxy-alpha-methylbenzeneethanamine
  • ALEPH-2
Categories
UNII
Z1I419DRZZ
CAS number
185562-00-9
Weight
Average: 255.38
Monoisotopic: 255.129300094
Chemical Formula
C13H21NO2S
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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U5-hydroxytryptamine receptor 2A
agonist
Human
U5-hydroxytryptamine receptor 2C
agonist
Human
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with (S)-Warfarin.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when 2,5-Dimethoxy-4-ethylamphetamine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with 3-isobutyl-1-methyl-7H-xanthine.
3,4-MethylenedioxyamphetamineThe risk or severity of serotonin syndrome can be increased when 3,4-Methylenedioxyamphetamine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of serotonin syndrome can be increased when 4-Bromo-2,5-dimethoxyamphetamine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
4-hydroxycoumarinThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with 4-hydroxycoumarin.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when 4-Methoxyamphetamine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of serotonin syndrome can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with 5-methoxy-N,N-dimethyltryptamine.
6-O-benzylguanineThe risk or severity of adverse effects can be increased when 2,5-Dimethoxy-4-ethylthioamphetamine is combined with 6-O-benzylguanine.
Food Interactions
Not Available

References

General References
Not Available
External Links
ChemSpider
8439835
BindingDB
50164337
ChEMBL
CHEMBL339611

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
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

Taxonomy

Classification
Not classified

Targets

Kind
Protein
Organism
Human
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. [PubMed:11191631]
Kind
Protein
Organism
Human
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. [PubMed:11191631]

Drug created on December 31, 2017 20:29 / Updated on November 02, 2018 07:48