Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Phenethylamine
- DrugBank Accession Number
- DB04325
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental
- Structure
Structure for Phenethylamine (DB04325)
- Weight
- Average: 121.1796
Monoisotopic: 121.089149357 - Chemical Formula
- C8H11N
- Synonyms
- 2-phenylethylamine
- benzeneethanamine
- beta-Phenylethylamine
- Phenylethylamine
- β-aminoethylbenzene
- β-phenethylamine
- External IDs
- FEMA NO. 3220
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism A5-hydroxytryptamine receptor 2A inhibitorHumans UPrimary amine oxidase Not Available Escherichia coli (strain K12) USerine protease 1 Not Available Humans UTrypsin-2 Not Available 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your software1,2-Benzodiazepine The risk or severity of CNS depression can be increased when Phenethylamine is combined with 1,2-Benzodiazepine. Acetazolamide The risk or severity of CNS depression can be increased when Acetazolamide is combined with Phenethylamine. Acetophenazine The risk or severity of CNS depression can be increased when Acetophenazine is combined with Phenethylamine. Agomelatine The risk or severity of CNS depression can be increased when Phenethylamine is combined with Agomelatine. Alfentanil The risk or severity of CNS depression can be increased when Alfentanil is combined with Phenethylamine. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenethylamines. These are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Phenethylamines
- Direct Parent
- Phenethylamines
- Alternative Parents
- 2-arylethylamines / Aralkylamines / Organopnictogen compounds / Monoalkylamines / Hydrocarbon derivatives
- Substituents
- 2-arylethylamine / Amine / Aralkylamine / Aromatic homomonocyclic compound / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Phenethylamine / Primary aliphatic amine
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- alkaloid, aralkylamine, phenylethylamine (CHEBI:18397) / Biogenic amines (C05332)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 327C7L2BXQ
- CAS number
- 64-04-0
- InChI Key
- BHHGXPLMPWCGHP-UHFFFAOYSA-N
- InChI
- InChI=1S/C8H11N/c9-7-6-8-4-2-1-3-5-8/h1-5H,6-7,9H2
- IUPAC Name
- 2-phenylethan-1-amine
- SMILES
- NCCC1=CC=CC=C1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0012275
- KEGG Compound
- C05332
- PubChem Compound
- 1001
- PubChem Substance
- 46507825
- ChemSpider
- 13856352
- BindingDB
- 10758
- 1309741
- ChEBI
- 18397
- ChEMBL
- CHEMBL610
- ZINC
- ZINC000006579654
- PDBe Ligand
- PEA
- Wikipedia
- 2-phenylethylamine
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Basic Science Amphetamine Abuse / Amphetamine-Related Disorders 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) -60 °C PhysProp boiling point (°C) 197.5 °C PhysProp logP 1.41 HANSCH,C ET AL. (1995) pKa 9.83 (at 25 °C) CRC Handbook Chem Physics (2000) - Predicted Properties
Property Value Source Water Solubility 2.19 mg/mL ALOGPS logP 1.41 ALOGPS logP 1.39 Chemaxon logS -1.7 ALOGPS pKa (Strongest Basic) 9.79 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 26.02 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 39.29 m3·mol-1 Chemaxon Polarizability 14.35 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9022 Blood Brain Barrier + 0.9358 Caco-2 permeable + 0.8705 P-glycoprotein substrate Non-substrate 0.7267 P-glycoprotein inhibitor I Non-inhibitor 0.9586 P-glycoprotein inhibitor II Non-inhibitor 0.9273 Renal organic cation transporter Non-inhibitor 0.5524 CYP450 2C9 substrate Non-substrate 0.8336 CYP450 2D6 substrate Substrate 0.6961 CYP450 3A4 substrate Non-substrate 0.7843 CYP450 1A2 substrate Inhibitor 0.7527 CYP450 2C9 inhibitor Non-inhibitor 0.7402 CYP450 2D6 inhibitor Inhibitor 0.6126 CYP450 2C19 inhibitor Inhibitor 0.5132 CYP450 3A4 inhibitor Non-inhibitor 0.9109 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6645 Ames test Non AMES toxic 0.8619 Carcinogenicity Non-carcinogens 0.7581 Biodegradation Ready biodegradable 0.9225 Rat acute toxicity 2.2561 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.6231 hERG inhibition (predictor II) Non-inhibitor 0.8105
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 124.7623203 predictedDarkChem Lite v0.1.0 [M-H]- 124.6915203 predictedDarkChem Lite v0.1.0 [M-H]- 124.7291203 predictedDarkChem Lite v0.1.0 [M-H]- 122.113266 predictedDeepCCS 1.0 (2019) [M+H]+ 125.4314203 predictedDarkChem Lite v0.1.0 [M+H]+ 125.2501203 predictedDarkChem Lite v0.1.0 [M+H]+ 125.6893203 predictedDarkChem Lite v0.1.0 [M+H]+ 124.894424 predictedDeepCCS 1.0 (2019) [M+Na]+ 124.9017203 predictedDarkChem Lite v0.1.0 [M+Na]+ 125.0113203 predictedDarkChem Lite v0.1.0 [M+Na]+ 124.8599203 predictedDarkChem Lite v0.1.0 [M+Na]+ 133.53111 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- 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
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- The enzyme prefers aromatic over aliphatic amines.
- Specific Function
- aliphatic amine oxidase activity
- Gene Name
- tynA
- Uniprot ID
- P46883
- Uniprot Name
- Primary amine oxidase
- Molecular Weight
- 84378.17 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Has activity against the synthetic substrates Boc-Phe-Ser-Arg-Mec, Boc-Leu-Thr-Arg-Mec, Boc-Gln-Ala-Arg-Mec and Boc-Val-Pro-Arg-Mec. The single-chain form is more active than the two-chain form against all of these substrates
- Specific Function
- metal ion binding
- Gene Name
- PRSS1
- Uniprot ID
- P07477
- Uniprot Name
- Serine protease 1
- Molecular Weight
- 26557.88 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- In the ileum, may be involved in defensin processing, including DEFA5
- Specific Function
- calcium ion binding
- Gene Name
- PRSS2
- Uniprot ID
- P07478
- Uniprot Name
- Trypsin-2
- Molecular Weight
- 26487.55 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Drug created at June 13, 2005 13:24 / Updated at August 26, 2024 19:22