Homoveratrylamine
HOMOVERATRYLAMINE · dmpea · 2-(3,4-Dimethoxyphenyl)ethanamine · DiMethoxyphenethylaMine · 2-(3,4-DIMETHOXYPHENYL)ETHYLAMINE · Dimethoxyphenylethylamine · Dopamine Hydrochloride EP Impurity C · HVTA
Identifiers & Physical Properties
| CAS No. | 120-20-7 |
|---|---|
| Molecular formula | C10H15NO2 |
| Average molar mass | 181.23 g/mol |
| Monoisotopic mass | 181.11027872 g/mol |
| SMILES | COc1ccc(CCN)cc1OC |
| InChIKey | ANOUKFYBOAKOIR-UHFFFAOYSA-N |
| PubChem CID | 8421 |
| ChEMBL | CHEMBL26019 |
| ChEBI | CHEBI:136995 |
| EC No. | 204-376-9 |
| DTXSID | DTXSID8059506 |
Chemical & Physical Properties
| XLogP | 0.8 |
|---|---|
| Topological polar surface area | 44.5 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 3 |
| Rotatable bonds | 4 |
| Heavy atoms | 13 |
| Formal charge | 0 |
| Complexity | 141 |
| Chemical classes | Nitrogen Compounds -> Other Aromatics (Nitrogen) |
| Drugs | DEA NFLIS-Drug Category -> Phenethylamines (Amphetamines) (H)Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds |
| LogP (partition coefficient) | 0.77 |
| Solubility | 24.8 [ug/mL] (The mean of the results at pH 7.4)Chloroform (Slightly), Methanol (Slightly)SOLUBLE |
| Boiling point | 163 - 165 °C188 °C15 mm Hg(lit.) |
| Vapor pressure | 0.00261 [mmHg]0.348-0.348Pa at 25℃ |
| Physical Description | Colorless liquid with an amine-like odor[Alfa Aesar MSDS]Solid |
| Melting point | 12-15 °C |
| Density | 1.074 g/mL at 25 °C(lit.) |
| Refractive index | n20/D 1.546(lit.) |
| Flash point | >230 °F |
| Storage conditions | Refrigerator |
| pKa (acidity coefficient) | 9.74±0.10(Predicted) |
| Physical state | Viscous Liquid |
| Specific gravity | 1.10 |
| Color | Clear light yellow to orange or slightly brownish |
| pH | 11.4 (100g/l, H2O, 20℃) |
| Explosive limits | 0.1-1.7%(V) |
| Sensitivity | 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 (partition coefficient) | 0.77 |
| CAS DataBase Reference | 120-20-7(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | IQF9T435OP |
| NIST Chemistry Reference | Benzeneethanamine, 3,4-dimethoxy-(120-20-7) |
| EPA Substance Registry System | Benzeneethanamine, 3,4-dimethoxy- (120-20-7) |
| UNSPSC Code | 41116107 |
| NACRES | NA.24 |
| GHS pictogram | GHS05,GHS07 |
| Signal word | Danger |
| GHS hazard statements | H302-H315-H317-H318 |
| GHS precautionary statements | P261-P264-P280-P301+P312-P302+P352-P305+P351+P338 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Hazard symbols | Xn,Xi |
| Risk statements (R) | 22-36/37/38 |
| Safety statements (S) | 26-36-37/39 |
| UN transport number | UN 2735 |
| Water hazard class (WGK) | 3 |
| RTECS number | SH2300000 |
| F | 10 |
| Hazard Note | Irritant |
| TSCA inventory status | TSCA listed |
| Hazard class | 8Acute Tox. 4 OralEye Dam. 1Skin Irrit. 2Skin Sens. 1B |
| Packing group | III |
| Customs code | 29222900 |
| Storage class | 10 - Combustible liquids |
| Toxicity | mouse,LD50,intraperitoneal,181mg/kg (181mg/kg),Yakugaku Zasshi. Journal of Pharmacy. Vol. 97, Pg. 1117, 1977. |
| REACH registrations | Active |
Safety & Regulations
| GHS classification | DangerH302 (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. |
|---|---|
| Regulatory information | Chemical: Benzeneethanamine, 3,4-dimethoxy-Status: Active Update: 26-06-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/224672-(3,4-Dimethoxyphenyl) ethylamine: Does not have an individual approval but may be used under an appropriate group standard |
| Hazards summary | Causes burnsInhalation may cause corrosive injuries to upper respiratory tract and lungsHarmful by ingestionToxic by inhalation[Alfa Aesar MSDS] |
| Hazard Classes and Categories | Acute Tox. 4 (99.5%) |
| Adverse effects | Dermatotoxin - Skin burns. |
| Toxicity Data | LC50 (rat) > 5,500 mg/m3/4hr |
| F | 10 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter |
| Water hazard class (WGK) | 3 |
| TSCA inventory status | TSCA listed |
| RTECS number | SH2300000 |
| UN transport number | UN 2735 |
| Customs code | 29222900 |
| Toxicity | mouse,LD50,intraperitoneal,181mg/kg (181mg/kg),Yakugaku Zasshi. Journal of Pharmacy. Vol. 97, Pg. 1117, 1977. |
| Risk statements (R) | 22-36/37/38 |
| Signal word | Danger |
| GHS pictogram | GHS05,GHS07 |
| Hazard symbols | Xn,Xi |
| hazard_note | Irritant |
| Safety statements (S) | 26-36-37/39 |
| Hazard class | 8Acute Tox. 4 OralEye Dam. 1Skin Irrit. 2Skin Sens. 1B |
| Storage class | 10 - Combustible liquids |
| Packing group | III |
| GHS hazard statements | H302-H315-H317-H318 |
| REACH registrations | Active |
| GHS precautionary statements | P261-P264-P280-P301+P312-P302+P352-P305+P351+P338 |
Applications & Uses
Description
3,4-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.
Occurrence
3,4-Dimethoxyphenethylamine is a natural product found in Pilosocereus leucocephalus, Vachellia rigidula, and Ototropis elegans with data available.
Uses
3,4-Dimethoxyphenethylamine is a methylated metabolite of Dopamine (D533780); a potent inhibitor of brain mitochondrial respiration used in Parkinson’s disease studies.
Uses
Precursor for the synthesis of isoquinolines.