Basic information
- CAS
1019-45-0- Standard SMILES
COc1ccc2[nH]cc(CCN(C)C)c2c1- InChIKey
ZSTKHSQDNIGFLM-UHFFFAOYSA-N- Molecular formula
- C13H18N2O
- Average molar mass
- 218.29 g/mol
- Monoisotopic mass
- 218.1419132
Overview
5-methoxy-N,N-dimethyltryptamine is a tryptamine alkaloid that is N,N-dimethyltryptamine substituted by a methoxy group at position 5. It has a role as a hallucinogen and a plant metabolite. It is an aromatic ether, a tryptamine alkaloid and a tertiary amino compound. It is functionally related to a bufotenin.
Names & identifiers
- Preferred name
- O-Methylbufotenine
- IUPAC
- 2-(5-methoxy-1H-indol-3-yl)-N,N-dimethylethanamine
- English name
- N,N-Dimethyl-5-methoxytryptamine
- Molecular formula
- C13H18N2O
- Molecular weight
- 218.29
Names & synonyms
5-Methoxy-N,N-dimethyltryptamineN,N-Dimethyl-5-methoxytryptamine1019-45-0O-Methylbufotenine5-MeO-DMTMeODMTMethylbufotenineBufotenine, O-methyl-3-(2-Dimethylaminoethyl)-5-methoxyindole2-(5-Methoxy-1H-indol-3-yl)-N,N-dimethylethanamine1H-Indole-3-ethanamine, 5-methoxy-N,N-dimethyl-CT 4334
Show more names
5-Methoxydimethyltryptaminect43345-OME-DMT5-METHOXY-DMTMethoxybufotenin
5-Methoxy-N,N-dimethyl-1H-indole-3-ethanamineNSC 88624EINECS 213-813-2NSC-886245-Methoxy-N,N-dimethyl-1H-indole-3-ethylamine3-(2-(N,N-Dimethyl)aminoethyl)-5-methoxyindoleBRN 0164771INDOLE, 3-(2-(N,N-DIMETHYLAMINO)ETHYL)-5-METHOXY-
Database identifiers
- CAS
1019-45-0- PubChem CID
- 1832
- DTXSID
DTXSID70144324- ChEMBL
CHEMBL7257- ChEBI
CHEBI:2086- UNII
- X0MKX3GWU9
- EC Number
- 213-813-2
- Nikkaji
- J21.248B
Properties
Computed structural properties
- XLogP
- 1.5
- Topological polar surface area
- 28.3 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 4
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 220
Experimental & physicochemical properties
Drugs
DEA Schedule I Controlled Substance -> Hallucinogenic substances
Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
Pharmaceuticals -> Listed in ZINC15
Solubility>32.7 [ug/mL] (The mean of the results at pH 7.4)
Human DrugsBreast Feeding; Lactation; Milk, Human; Hallucinogens; Serotonin Antagonists
Physical DescriptionSolid
Collision Cross Section
153.76 Ų [M-H]- [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]
150.3 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
Physicochemical properties
- Melting point
- 69 °C · 69 °C
- Boiling point
- 358.99 °C · 358.99°C (rough estimate)
- Density
- 1.0346 · 1.0346 (rough estimate)
- refractive index
- 1.645 · 1.6450 (estimate)
- storage temp.
- 0 · 0-6°C
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- pka
- 16.94 · 16.94±0.30(Predicted)
- form
- Solid
- color
- Pale Beige
- Water Solubility
- PRACTICALLY INSOLUBLE
- Major Application
- forensics and toxicology
- InChI
- 1S/C13H18N2O/c1-15(2)7-6-10-9-14-13-5-4-11(16-3)8-12(10)13/h4-5,8-9,14H,6-7H2,1-3H3
- InChIKey
- ZSTKHSQDNIGFLM-UHFFFAOYSA-N
- SMILES
- CN(C)CCC1=CNC2=CC=C(OC)C=C21
- CAS DataBase Reference
- 1019 · 1019-45-0(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 0 MKX3GWU9 · X0MKX3GWU9
- NIST Chemistry Reference
- 1 H-Indole-3-ethanamine, · 1H-Indole-3-ethanamine, 5-methoxy-N,N-dimethyl-(1019-45-0)
- UNSPSC Code
- 41116107 · 41116107
- NACRES
- 24 · NA.24
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 332 · H332
- Precautionary statements
- 261 · P261-P271-P304+P340-P312
- target organs
- Eyes
- Hazard Codes
- C,Xn
- Risk Statements
- 20 · 20-34-43-21/22
- Safety Statements
- 22 · 22-26-28A-36/37/39-45-36-24/25
- RIDADR
- 1230 · UN1230 - class 3 - PG 2 - Methanol, solution
- WGK Germany
- 2 · WGK 2
- RTECS
- 7380000 · NL7380000
- HS Code
- 29339980 · 29339980
- Storage Class
- 3 · 3 - Flammable liquids
- Hazard Classifications
- 3 DermalAcute · Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H332 (95.1%): Harmful if inhaled [Warning Acute toxicity, inhalation]
P261, P271, P304+P340, and P317 (click each P-code to see the statement)
Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory InformationDEA schedule I controlled substance
Hazard Classes and CategoriesAcute Tox. 4 (95.1%)
Toxicology
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- wgk
- WGK 2
- rtecs
- NL7380000
- ridadr
- UN1230 - class 3 - PG 2 - Methanol, solution
- hs_code
- 29339980
- risk_code
- 20-34-43-21/22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- C,Xn
- safety_code
- 22-26-28A-36/37/39-45-36-24/25
- Storage Class
- 3 - Flammable liquids
- target organs
- Eyes
- Hazard statements
- H332
- Hazard Classifications
- Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralFlam. Liq. 2STOT SE 1
- Precautionary statements
- P261-P271-P304+P340-P312
Chemistry & industry
Pharmacology
Metabolism/MetabolitesN,n-dimethyl-5-methoxytryptamine has known human metabolites that include Bufotenine.
Cellular LocationsMembrane
Applications
DescriptionObtained from Desmodium pulchellum Benth ex Baker, and also from Phalaris tuberosa L., this indole alkaloid is best crystallized from Et20-light petroleum when it yields colourless rectangular plates. It is optically inactive and the ultraviolet spectrum has absorption maxima at 224, 277 and 296 mil. It forms a crystalline picrate as orange-yellow needles, m.p. 176-7°C and the methiodide, m.p. 181-2°C.
UsesHallucinogen; non-selective serotonin receptor agonist
Uses5-Methoxy-N,N-dimethyltryptamine is a tryptamine derivative and a full potent agonist used in the study of mammalian hormones to stimukate cAMP formation by colliculi neurons and mediate serotoninergic receptors. It is a natural hallucinogen component of Ayahuasca, an Amazonian beverage and is currently being made as a designer drug.
Additional notes
DefinitionChEBI: A tryptamine alkaloid that is N,N-dimethyltryptamine substituted by a methoxy group at position 5.
Related reactions
1 records
Compound notes
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