Basic information
- CAS
2235-90-7- Standard SMILES
CCC(N)Cc1c[nH]c2ccccc12- InChIKey
ZXUMUPVQYAFTLF-UHFFFAOYSA-N- Molecular formula
- C12H16N2
- Average molar mass
- 188.27 g/mol
- Monoisotopic mass
- 188.13134852
Names & identifiers
- Preferred name
- Alpha-Ethyltryptamine
- IUPAC
- 1-(1H-indol-3-yl)butan-2-amine
- English name
- α-Ethyltryptamine
- Molecular formula
- C12H16N2
- Molecular weight
- 188.27
Names & synonyms
ETRYPTAMINEalpha-Ethyltryptamine3-(2-Aminobutyl)indole2235-90-73-IndolylbutylamineEtriptaminaMonaseRo 3-1932Etryptaminum1H-Indole-3-ethanamine, alpha-ethyl-alphaETDTXSID1046764
Show more names
AURORA KA-7710Ethyltryptamineα-EthyltryptamineA-ETHYLTRYPTAMINE HCL
NSC-88061GR181O3R32DTXCID9026764NSC880612-ethyltryptamine3-(2-aminobutylindole)RefChem:1393041-(1H-indol-3-yl)butan-2-amine
Database identifiers
- CAS
2235-90-7- PubChem CID
- 8367
- DTXSID
DTXSID1046764- ChEMBL
CHEMBL1619758- ChEBI
CHEBI:134838- UNII
- GR181O3R32
- Nikkaji
- J7.373C
Properties
Computed structural properties
- XLogP
- 2.5
- Topological polar surface area
- 41.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 3
- Heavy atoms
- 14
- Formal charge
- 0
- Complexity
- 181
Experimental & physicochemical properties
LogS-2.57
Solubility510
Melting Point221
Kovats Retention Index1848
Physicochemical properties
- Melting point
- 97 · 97-99°
- Boiling point
- 313.29 °C · 313.29°C (rough estimate)
- Density
- 0.952 · 0.9520 (rough estimate)
- refractive index
- 1.56 · 1.5600 (estimate)
- solubility
- 11 mg/ml; · DMF: 11 mg/ml; DMSO: 5 mg/ml; Ethanol: 20 mg/ml; Ethanol:PBS(pH 7.2) (1:1): 0.5 mg/ml
- form
- A crystalline solid
- pka
- 17.22 · 17.22±0.30(Predicted)
- Water Solubility
- 0.51 g/L · 0.51g/L(room temperature)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 181 O3R32 · GR181O3R32
Safety & regulation
Hazard information
Regulatory InformationDEA schedule I controlled substance
Regulatory information
Regulatory InformationDEA schedule I controlled substance
Chemistry & industry
Pharmacology
PharmacodynamicsαET is a stimulant and psychedelic with MDMA like physiological effects. Like MDMA, increases in locomotor activity and mood elevation can be seen post administration. [2]
Mechanism of Action
The mechanism of action responsible for its antidepressant activity was believed to lie in its ability to inhibit monoamine oxidase, while its stimulant activity on the central nervous system appeared to result from its structural similarity to indole-based psychedelics. [5] Research discovered αET to be both a monoamine oxidase inhibitor and a potent monoamine releasing agent capable of serotonergic neurotoxicity. [3] The ability to release serotonin was linked to αET's MDMA like properties. [2] αET has been shown to release serotonin pre-synaptically, as well as lesser amounts of norepinephrine and dopamine.
Applications
Usesα-Ethyltryptamine (E931900) is used as a stimulant and entactogen that have actions at multiple central nervous system (CNS) receptor sites.
Upstream & downstream products
Upstream raw materials
Additional notes
DefinitionChEBI: Etryptamine is a member of indoles.
Related reactions
4 records
Compound notes
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