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4-Br-3,5-DMA

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EntityQ4637107· pop 5· linked from 8 articles

4-Br-3,5-DMA

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Also known as 4,3,5-DOB, 3,5-dimethoxy-4-bromoamphetamine, 4-bromo-3,5-dimethoxyamphetamine, 4-ethyl-2-methoxy-5-methylthioamphetamine, 1-(4-bromo-3,5-dimethoxyphenyl)propan-2-amine

4-Br-3,5-DMA, also known as 4-bromo-3,5-dimethoxyamphetamine or as 4-bromo-TMA, is a psychoactive drug of the phenethylamine, amphetamine, and 3C families related to mescaline. It is the analogue of TMA in which the methoxy group at the 4 position has been replaced with a bromine atom. In addition, 4-Br-3,5-DMA is a positional isomer of DOB with the methoxy group at the 2 position located instead at the 3 position.

In the Vinony graph

Vinony's link graph records 8 inbound references to 4-Br-3,5-DMA, and connects out to 2C-G, N-methylserotonin and D-methamphetamine.

It is catalogued under topics including 3C (psychedelics), Analgesics and Bromobenzene derivatives.

Vinony links it to 5 Wikipedia language editions.

Chemical data

Formula
C11H16BrNO2
Molecular weight
274.15 g/mol
IUPAC name
1-(4-bromo-3,5-dimethoxyphenyl)propan-2-amine
SMILES
CC(CC1=CC(=C(C(=C1)OC)Br)OC)N
InChIKey
FAVLJTSHWBEOMA-UHFFFAOYSA-N
XLogP
2.4
Polar surface area
44.5 Ų
H-bond donors
1
H-bond acceptors
3
Formal charge
0

via PubChem

Drug data · ChEMBL

Molecule type
Small molecule

via ChEMBL · EBI

Wikidata facts

Subclass of
phenethylamine
Has part
bromine
Mass
273.036440852
Show 5 more facts
chemical formula
C₁₁H₁₇NO₂Br
canonical SMILES
C1=C(C(=C(C=C1CC(C)N)OC)Br)OC
discoverer or inventor
Alexander Shulgin
subject has role
psychoactive drug
Sources (1)

via Wikidata · CC0

~3 min read

Encyclopedic overview

10 sections
Contents
  • Use and effects
  • Pharmacology
  • Pharmacodynamics
  • Chemistry
  • Synthesis
  • Analogues
  • History
  • See also
  • References
  • External links

4-Br-3,5-DMA, also known as 4-bromo-3,5-dimethoxyamphetamine or as 4-bromo-TMA, is a psychoactive drug of the phenethylamine, amphetamine, and 3C families related to mescaline. It is the analogue of TMA in which the methoxy group at the 4 position has been replaced with a bromine atom. In addition, 4-Br-3,5-DMA is a positional isomer of DOB with the methoxy group at the 2 position located instead at the 3 position.

==Use and effects== In his book PiHKAL (Phenethylamines I Have Known and Loved) and other publications, Alexander Shulgin lists 4-Br-3,5-DMA's dose range as 4 to 10mg orally and its duration as 8 to 12hours. In earlier publications, the dose range was listed as 3 to 6mg orally and was described as producing threshold effects. The effects of 4-Br-3,5-DMA have been reported to include very shallow threshold effects to a "plus-two" on the Shulgin Rating Scale depending on dose, very little if any sensory distortion, pronounced analgesia or tactile anesthesia and numbing of the skin and extremities, and teeth rubbiness. Although it produces both mental and physical effects, there were no clear hallucinogenic or visual effects at tested doses. Shulgin said that it is a "remarkably effective anesthetic to skin surfaces" taken systemically at his listed doses and suggested that it might be a "narcotic" rather than a psychedelic.

Excerpted from Wikipedia’s “4-Br-3,5-DMA” article, available under the CC BY-SA 4.0 licence.

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