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
Show more names
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
- Formal charge
- 0
- Complexity
- 141
Experimental & physicochemical properties
Drugs
DEA NFLIS-Drug Category -> Phenethylamines (Amphetamines) (H)
Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
Physical Description
Colorless liquid with an amine-like odor; [Alfa Aesar MSDS]
Solid
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
- storage temp.
- Refrigerator
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- pka
- 9.74 · 9.74±0.10(Predicted)
- form
- Viscous Liquid
- Specific Gravity
- 1.1 · 1.10
- color
- Clear light yellow to orange or slightly brownish
- PH
- 11.4 · 11.4 (100g/l, H2O, 20℃)
- explosive limit
- 0.1 · 0.1-1.7%(V)
- Water Solubility
- SOLUBLE
- Sensitive
- Air Sensitive
- InChI
- 1S/C10H15NO2/c1-12-9-4-3-8(5-6-11)7-10(9)13-2/h3-4,7H,5-6,11H2,1-2H3
- InChIKey
- ANOUKFYBOAKOIR-UHFFFAOYSA-N
- SMILES
- COc1ccc(CCN)cc1OC
- LogP
- 0.77 · 0.77
- CAS DataBase Reference
- 120 · 120-20-7(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 9 T435OP · IQF9T435OP
- NIST Chemistry Reference
- 3 · Benzeneethanamine, 3,4-dimethoxy-(120-20-7)
- EPA Substance Registry System
- 3 · Benzeneethanamine, 3,4-dimethoxy- (120-20-7)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 5 · GHS05,GHS07
- Signal word
- Danger
- Hazard statements
- 302 · H302-H315-H317-H318
- Precautionary statements
- 261 · P261-P264-P280-P301+P312-P302+P352-P305+P351+P338
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- Hazard Codes
- Xn,Xi
- Risk Statements
- 22 · 22-36/37/38
- Safety Statements
- 26 · 26-36-37/39
- RIDADR
- 2735 · UN 2735
- WGK Germany
- 3 · 3
- RTECS
- 2300000 · SH2300000
- F
- 10 · 10
- Hazard Note
- Irritant
- TSCA
- TSCA listed
- HazardClass
- 8 · 8
- PackingGroup
- III
- HS Code
- 29222900 · 29222900
- Storage Class
- 10 · 10 - Combustible liquids
- Hazard Classifications
- 4 OralEye · Acute Tox. 4 OralEye Dam. 1Skin Irrit. 2Skin Sens. 1B
- Toxicity
- 50 · mouse,LD50,intraperitoneal,181mg/kg (181mg/kg),Yakugaku Zasshi. Journal of Pharmacy. Vol. 97, Pg. 1117, 1977.
- REACH Registrations
- Active
Safety & regulation
GHS classification
GHS Classification
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
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
Toxicology
Safety data
- F
- 10
- PPE
- Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- SH2300000
- ridadr
- UN 2735
- hs_code
- 29222900
- Toxicity
- mouse,LD50,intraperitoneal,181mg/kg (181mg/kg),Yakugaku Zasshi. Journal of Pharmacy. Vol. 97, Pg. 1117, 1977.
- risk_code
- 22-36/37/38
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS07
- hazard_code
- Xn,Xi
- hazard_note
- Irritant
- safety_code
- 26-36-37/39
- hazard_class
- 8
- Storage Class
- 10 - Combustible liquids
- packing_group
- III
- Hazard statements
- H302-H315-H317-H318
- REACH Registrations
- Active
- Hazard Classifications
- Acute Tox. 4 OralEye Dam. 1Skin Irrit. 2Skin Sens. 1B
- Precautionary statements
- P261-P264-P280-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Uses & manufacturing
Applications
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.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
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
Linked notes
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