Basic information
- CAS
64584-34-5- Standard SMILES
COc1cc(CC(C)N)c(OC)cc1I- InChIKey
BGMZUEKZENQUJY-UHFFFAOYSA-N- Molecular formula
- C11H16INO2
- Average molar mass
- 321.15 g/mol
- Monoisotopic mass
- 321.02258
Overview
2-(4-iodo-2,5-dimethoxyphenyl)-1-methylethylamine is an organoiodine compound that is amphetamine bearing two methoxy substituents at positions 2 and 5 as well as an iodo substituent at position 4. It is a member of amphetamines, an organoiodine compound and a dimethoxybenzene. It is functionally related to an amphetamine.
Names & identifiers
- Preferred name
- 2,5-Dimethoxy-4-iodoamphetamine
- IUPAC
- 1-(4-iodo-2,5-dimethoxyphenyl)propan-2-amine
- English name
- 1-(4-IODO-2,5-DIMETHOXYPHENYL)PROPAN-2-AMINE
- Molecular formula
- C11H16INO2
- Molecular weight
- 321.16
Names & synonyms
64584-34-54-DOI4-Iodo-2,5-dimethoxyphenylisopropylamine2,5-Dimethoxy-4-iodoamphetamineDOI-P1-(2,5-Dimethoxy-4-iodophenyl)-2-aminopropane2,5-Dimethoxy-4-iodophenylisopropylamine1-(4-Iodo-2,5-dimethoxyphenyl)-2-aminopropaneOOM10GW9UEDTXSID70405204-Iodo-2,5-dimethoxy-alpha-methylbenzeneethanamineDOI cpd
Show more names
AURORA KA-76724-Iodo-2,5-dieMthoxyaMphetaMine2,5-DiMethoxy-4-iodoMethaMphetaMine1-(4-IODO-2,5-DIMETHOXYPHENYL)PROPAN-2-AMINE4-Iodo-2,5-diMethoxy-α-MethylbenzeneethanaMine4-iodo-3-methoxy-N-(1-methoxypropan-2-yl)anilineBenzeneethanamine, 4-iodo-2,5-dimethoxy-α-methyl-4-Iodo-2,5-dimethoxyphenylisopropylamine hydrochloride, (R)-isomer
RefChem:908825DTXCID5020520DOI4-Iodo-2,5-dimethoxyamphetamine2-(4-iodo-2,5-dimethoxyphenyl)-1-methylethylamine(+/-)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropaneCHEMBL6616UNII-OOM10GW9UE
Properties
Computed structural properties
- XLogP
- 2.5
- Topological polar surface area
- 44.5 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 3
- Rotatable bonds
- 4
- Heavy atoms
- 15
- Formal charge
- 0
- Complexity
- 191
Experimental & physicochemical properties
Drugs
DEA NFLIS-Drug Category -> Phenethylamines (D Series) (H)
Pharmaceuticals -> Synthetic Cannabinoids or Psychoactive Compounds
Physicochemical properties
- Boiling point
- 361.5 · 361.5±42.0 °C(Predicted)
- Density
- 1.508 · 1.508±0.06 g/cm3(Predicted)
- pka
- 9.46 · 9.46±0.10(Predicted)
- FDA UNII
- 10 GW9UE · OOM10GW9UE
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301
- Precautionary statements
- 264 · P264-P270-P301+P310-P405-P501
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- Hazard statements
- H301
- Precautionary statements
- P264-P270-P301+P310-P405-P501
Chemistry & industry
Pharmacology
MeSH Pharmacological Classification
Drugs capable of inducing illusions, hallucinations, delusions, paranoid ideations, and other alterations of mood and thinking. Despite the name, the feature that distinguishes these agents from other classes of drugs is their capacity to induce states of altered perception, thought, and feeling that are not experienced otherwise.
Endogenous compounds and drugs that bind to and activate SEROTONIN RECEPTORS. Many serotonin receptor agonists are used as ANTIDEPRESSANTS; ANXIOLYTICS; and in the treatment of MIGRAINE DISORDERS.
Applications
Uses2,5-Dimethoxy-4-iodoamphetamine (DOI) is a psychedelic drug and a substituted amphetamine of the phenethylamine family. It is also a powerful anti-inflammatory that is effective at doses on the order of 100 micrograms in humans, far below its effective dose as a psychedelic. Despite being a substituted amphetamine, it is not a stimulant. DOI has a stereocenter and R-(-)-DOI is the more active stereoisomer. DOI is a 5-HT2A, 5-HT2B, and 5-HT2C receptor partial agonist. Its psychedelic effects are mediated by its agonistic properties at the 5-HT2A receptor. This is a controlled substance.
Suppliers5 total
淄博容纳生物科技有限公司+86-86-13583358881 +8618560316533 · [email protected]
凯试(上海)科技有限公司021-50135380 · [email protected]
Shanghai Safer Pharmaceutical Technology Co., Ltd.021-31761238 · [email protected]
赛纳斯特化学（欢迎点击联系）021-60343070
池州凯隆进出口贸易有限公司[email protected]
Related reactions
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Compound notes
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