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2,5-Dimethoxy-4-ethylthioamphetamine

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

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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
3D
Similar Structures
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
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available
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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
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interactions in your software
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when 1,2-Benzodiazepine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
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.
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

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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
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
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4r-0290000000-d7c93931c80f66bced7e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-2290000000-47b3b85f0298cfdeb01c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-06vi-3950000000-e13cb2444a6b6481493c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-08fr-9540000000-0687d336cbe8e561e5e2
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-8910000000-f9698c2c2b5f8410a829
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-9410000000-aaae964585780c0193ab
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

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Details1. 5-hydroxytryptamine receptor 2A
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin) (PubMed:1330647, PubMed:18703043, PubMed:19057895, PubMed:21645528, PubMed:22300836, PubMed:35084960, PubMed:38552625). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD) (PubMed:28129538, PubMed:35084960). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of downstream effectors (PubMed:28129538, PubMed:35084960). HTR2A is coupled to G(q)/G(11) G alpha proteins and activates phospholipase C-beta, releasing diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) second messengers that modulate the activity of phosphatidylinositol 3-kinase and promote the release of Ca(2+) ions from intracellular stores, respectively (PubMed:18703043, PubMed:28129538, PubMed:35084960). Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways (PubMed:28129538, PubMed:35084960). Affects neural activity, perception, cognition and mood (PubMed:18297054). Plays a role in the regulation of behavior, including responses to anxiogenic situations and psychoactive substances. Plays a role in intestinal smooth muscle contraction, and may play a role in arterial vasoconstriction (By similarity)
Specific Function
1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine binding
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]
Details2. 5-hydroxytryptamine receptor 2C
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Agonist
General Function
G-protein coupled receptor for 5-hydroxytryptamine (serotonin) (PubMed:12970106, PubMed:18703043, PubMed:19057895, PubMed:29398112, PubMed:7895773). Also functions as a receptor for various drugs and psychoactive substances, including ergot alkaloid derivatives, 1-2,5,-dimethoxy-4-iodophenyl-2-aminopropane (DOI) and lysergic acid diethylamide (LSD) (PubMed:19057895, PubMed:29398112). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of downstream effectors (PubMed:18703043, PubMed:29398112). HTR2C is coupled to G(q)/G(11) G alpha proteins and activates phospholipase C-beta, releasing diacylglycerol (DAG) and inositol 1,4,5-trisphosphate (IP3) second messengers that modulate the activity of phosphatidylinositol 3-kinase and promote the release of Ca(2+) ions from intracellular stores, respectively (PubMed:18703043, PubMed:29398112). Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways (PubMed:29398112). Regulates neuronal activity via the activation of short transient receptor potential calcium channels in the brain, and thereby modulates the activation of pro-opiomelanocortin neurons and the release of CRH that then regulates the release of corticosterone (By similarity). Plays a role in the regulation of appetite and eating behavior, responses to anxiogenic stimuli and stress (By similarity). Plays a role in insulin sensitivity and glucose homeostasis (By similarity)
Specific Function
1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine binding
Gene Name
HTR2C
Uniprot ID
P28335
Uniprot Name
5-hydroxytryptamine receptor 2C
Molecular Weight
51804.645 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