Hydroxyamfetamine

HCID 3651

Notes Reactions

Substructure search Find similar structures

Basic information

CAS: 103-86-6
Standard SMILES: CC(N)Cc1ccc(O)cc1
InChIKey: GIKNHHRFLCDOEU-UHFFFAOYSA-N
Molecular formula: C9H13NO
Average molar mass: 151.21 g/mol
Monoisotopic mass: 151.09971404

Overview

4-(2-aminopropyl)phenol is a member of amphetamines.

Names & identifiers

Preferred name: Hydroxyamfetamine
IUPAC: 4-(2-aminopropyl)phenol
English name: 4-(2-aminopropyl)phenol
Molecular formula: C9H13NO
Molecular weight: 151.21

Names & synonyms

4-(2-Aminopropyl)phenolhydroxyamphetamine103-86-6HydroxyamfetamineNorveritolPulsotonOxamphetaminiumOksamfetaminOxamfetaminParedrinexNov-Pholedrinp-(2-Aminopropyl)phenol

Show more names

Norpholedrinep-Hydroxyamphetamine.alpha.-MethyltyraminePhenol,4-(2-aminopropyl)-Dl-p-(2-aminopropyl)phenol4-Hydroxy-.alpha.-methylphenethylamine2-(4-Hydroxyphenyl)-1-methylethylamine

Phenol, p-(2-aminopropyl)-DL-p-Hydroxyamphetamine1-p-Hydroxyphenyl-2-propylaminedl-4-hydroxyamphetamine2-Amino-1-(p-hydroxyphenyl)propaneNSC 170995Hydroxyamfetamine [INN]Hidroxianfetamina

Database identifiers

CAS: 103-86-6
PubChem CID: 3651
DTXSID: DTXSID3023134
ChEMBL: CHEMBL1546
ChEBI: CHEBI:103855
UNII: FQR280JW2N
EC Number: 203-152-8
Nikkaji: J182.169E

Properties

Computed structural properties

XLogP: 1.4
Topological polar surface area: 46.3 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 2
Rotatable bonds: 2
Heavy atoms: 11
Formal charge: 0
Complexity: 108

Experimental & physicochemical properties

DrugsDEA NFLIS-Drug Category -> Phenethylamines (Amphetamines) (S)

Physicochemical properties

Melting point: 125 · 125-126 °C
Boiling point: 279.2 · 279.2±15.0 °C(Predicted)
Density: 1.07 · 1.070±0.06 g/cm3(Predicted)
storage temp.: -20 °C · Store at -20°C
form: Solid
pka: 9.83 · 9.83±0.15(Predicted)
color: White to off-white
FDA UNII: 280 JW2N · FQR280JW2N
Symbol(GHS): 7 · GHS07,GHS05
Signal word: Danger
Hazard statements: 318 · H318-H315-H302-H335
Precautionary statements: 264 · P264-P270-P301+P312-P330-P501-P280-P305+P351+P338-P310-P264-P280-P302+P352-P321-P332+P313-P362
Toxicity: 100 mg/kg · LDLo intravenous in rat: 100mg/kg

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P319, P321, P330, P332+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

Toxicity: LDLo intravenous in rat: 100mg/kg
Signal word: Danger
Symbol(GHS): GHS07,GHS05
Hazard statements: H318-H315-H302-H335
Precautionary statements: P264-P270-P301+P312-P330-P501-P280-P305+P351+P338-P310-P264-P280-P302+P352-P321-P332+P313-P362

Chemistry & industry

Pharmacology

Protein BindingIntended for local use only (ophthalmic use).

Mechanism of ActionHydroxyamphetamine hydrobromide is an indirect acting sympathomimetic agent which causes the release of norepinephrine from adrenergic nerve terminals, resulting in mydriasis.

Metabolism/Metabolites · 2 items

Intended for local use only (ophthalmic use).

4-Hydroxyamphetamine is a known human metabolite of Amphetamine.

FDA Pharmacological Classification · 5 items

FQR280JW2N

HYDROXYAMPHETAMINE

Mechanisms of Action [MoA] - Adrenergic Agonists

Established Pharmacologic Class [EPC] - Adrenergic Receptor Agonist

Hydroxyamphetamine is an Adrenergic Receptor Agonist. The mechanism of action of hydroxyamphetamine is as an Adrenergic Agonist.

Absorption, Distribution and Excretion · 4 items

Intended for local use only (ophthalmic use).

Tissue LocationsKidney

Applications

Usesp-Hydroxyamphetamine is a major metabolite of Amphetamine (A634240), a sympathomimetic and psychotropic drug which is extensively metabolized in liver and in brain.