Homoveratrylamine

HCID 8421CAS 120-20-7

Basic information

Standard SMILES
COc1ccc(CCN)cc1OC
InChIKey
ANOUKFYBOAKOIR-UHFFFAOYSA-N
Molecular formula
C10H15NO2
Average molar mass
181.23 g/mol
Monoisotopic mass
181.11027872

Overview

3,4-dimethoxyphenylethylamine is an aromatic ether that is the derivative of 2-phenylethylamine with methoxy substituents at the 3- and 4-positions. It is an alkaloid isolated from the Cactaceae family. It has a role as an allergen and a plant metabolite. It is an alkaloid, an aromatic ether and a phenylethylamine. It derives from a hydride of a 2-phenylethylamine.

Names & identifiers

Preferred name
Homoveratrylamine
IUPAC
2-(3,4-dimethoxyphenyl)ethanamine
English name
3,4-Dimethoxyphenethylamine
Molecular formula
C10H15NO2
Molecular weight
181.23

Names & synonyms

3,4-Dimethoxyphenethylamine120-20-7Homoveratrylamine3,4-Dimethoxyphenylethylamine2-(3,4-Dimethoxyphenyl)ethylamineBenzeneethanamine, 3,4-dimethoxy-DimethoxydopamineDimethylmescalineDMPEA3,4-DimethoxybenzeneethanamineDopamine dimethyl etherDIMPEA
Show more names
2-(3,4-Dimethoxyphenyl)ethanamineDiMethoxyphenethylaMineDimethoxyphenylethylamineDopamine Hydrochloride EP Impurity CHVTAHomoveratrile Amine3,4-DIMETHOXY PHENYLETHYLAMINE
O,O-Dimethyldopamine3,4-Di-O-methyldopamine3,4-Dimethoxydopamine2-(3,4-Dimethoxyphenyl)Ethan-1-Amine3,4-Dimethoxyphenylethylamine(base)3,4-Dimethoxy-beta-phenylethylaminebeta-(3,4-Dimethyoxyphenyl)ethylamineNSC 16948

Database identifiers

CAS
120-20-7
PubChem CID
8421
DTXSID
DTXSID8059506
ChEMBL
CHEMBL26019
ChEBI
CHEBI:136995
UNII
IQF9T435OP
EC Number
204-376-9
Nikkaji
J28.381I

Properties

Computed structural properties

XLogP
0.8
Topological polar surface area
44.5 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
4
Heavy atoms
13

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Other Aromatics (Nitrogen)
Drugs · 2 items

DEA NFLIS-Drug Category -> Phenethylamines (Amphetamines) (H)

Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds

LogP0.77
Solubility24.8 [ug/mL] (The mean of the results at pH 7.4)
Boiling Point163 - 165 °C
Vapor Pressure0.00261 [mmHg]

Physicochemical properties

Melting point
12 · 12-15 °C
Boiling point
188 °C15 · 188 °C15 mm Hg(lit.)
Density
1.074 g/mL · 1.074 g/mL at 25 °C(lit.)
vapor pressure
0.348 · 0.348-0.348Pa at 25℃
refractive index
20 · n20/D 1.546(lit.)
Flash point
230 °F · >230 °F

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H302 (99.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 203 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

Chemical: Benzeneethanamine, 3,4-dimethoxy-

Status: Active Update: 26-06-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/22467

2-(3,4-Dimethoxyphenyl) ethylamine: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummaryCauses burns; Inhalation may cause corrosive injuries to upper respiratory tract and lungs; Harmful by ingestion; Toxic by inhalation; [Alfa Aesar MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (99.5%)

Toxicology

Adverse EffectsDermatotoxin - Skin burns.
Toxicity DataLC50 (rat) > 5,500 mg/m3/4hr

Safety data

F
10
PPE
Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
rtecs
SH2300000
ridadr
UN 2735

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationBenzeneethanamine, 3,4-dimethoxy-: ACTIVE
Applications · 4 items

Description3,4-Dimethoxyphenylethylamine, also known as 3,4-DMPEA or DMPEA is an endogenous metabolite found in urine that belongs to both the phenethylamine and catecholamine families. DMPEA is an analogue of dopamine (3,4-dihydroxyphenethylamine), with a substitution of the hydroxy groups with methoxy groups. It is also structurally similar to mescaline (3,4,5-trimethoxyphenylethylamine) and occurs naturally alongside it in various species of cacti such as the San Pedro and Peruvian Torch. DMPEA received wide attention after it was proposed as a biomarker in schizophrenic patients urine, however later studies revealed that DMPEA is also excreted by non-schizophrenics. DMPEA has little known bioactivity, but it has some action as a monoamine oxidase inhibitor. It has also been shown to have neurotoxic effects, especially in the nigrostriatal system and among dopaminergic neurons. DMPEA appears to be an inhibitor of mitochondrial complex I.

Occurrence3,4-Dimethoxyphenethylamine is a natural product found in Pilosocereus leucocephalus, Vachellia rigidula, and Ototropis elegans with data available.

Uses3,4-Dimethoxyphenethylamine is a methylated metabolite of Dopamine (D533780); a potent inhibitor of brain mitochondrial respiration used in Parkinson’s disease studies.

UsesPrecursor for the synthesis of isoquinolines.

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
韶远科技(上海)有限公司021-50795510 4000665055 · [email protected]

Additional notes

DefinitionChEBI: An aromatic ether that is the derivative of 2-phenylethylamine with methoxy substituents at the 3- and 4-positions. It is an alkaloid isolated from the Cactaceae family.

Related reactions

257 records

Linked notes

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