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5-bromodimethyltryptamine

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5-bromodimethyltryptamine

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5-Bromo-DMT, or 5-Br-DMT, also known as '5-bromo-N,N-dimethyltryptamine or by informal names like sea DMT or SpongeBob DMT', is a psychedelic drug and brominated indole alkaloid of the tryptamine family related to dimethyltryptamine (DMT). It is the 5-bromo derivative of DMT. The drug is naturally occurring in the sponges Smenospongia aurea and Smenospongia echina, as well as in Verongula rigida (0.00142% dry weight) alongside 5,6-dibromo-DMT (0.35% dry weight) and seven other alkaloids. It has been encountered as a novel designer drug.

Chemical data

Formula
C12H15BrN2
Molecular weight
267.16 g/mol
IUPAC name
2-(5-bromo-1H-indol-3-yl)-N,N-dimethylethanamine
SMILES
CN(C)CCC1=CNC2=C1C=C(C=C2)Br
InChIKey
ATEYZYQLBQUZJE-UHFFFAOYSA-N
XLogP
2.2
Polar surface area
19 Ų
H-bond donors
1
H-bond acceptors
1
Formal charge
0

via PubChem

Drug data · ChEMBL

Molecule type
Small molecule

via ChEMBL · EBI

Wikidata facts

Mass
266.042
Show 2 more facts
canonical SMILES
CN(C)CCC1=CNC2=C1C=C(C=C2)Br
chemical formula
C₁₂H₁₅BrN₂
Sources (2)

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~4 min read

Encyclopedic overview

16 sections
Contents
  • Use and effects
  • Interactions
  • Pharmacology
  • Pharmacodynamics
  • Chemistry
  • Synthesis
  • Analogues
  • History
  • Society and culture
  • Legal status
  • Canada
  • Singapore
  • United States
  • See also
  • References
  • External links

5-Bromo-DMT, or 5-Br-DMT, also known as '5-bromo-N,N-dimethyltryptamine or by informal names like sea DMT or SpongeBob DMT', is a psychedelic drug and brominated indole alkaloid of the tryptamine family related to dimethyltryptamine (DMT). It is the 5-bromo derivative of DMT. The drug is naturally occurring in the sponges Smenospongia aurea and Smenospongia echina, as well as in Verongula rigida (0.00142% dry weight) alongside 5,6-dibromo-DMT (0.35% dry weight) and seven other alkaloids. It has been encountered as a novel designer drug.

==Use and effects== 5-Bromo-DMT was only briefly mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved) and its properties and effects were not described. Subsequently, the drug has been reported by others to have a dose of 20 to 50mg smoked and a duration of 15minutes to 1.5hours. It is minimally active or inactive orally. It was described as producing mild psychedelic effects, such as visuals, pronounced tactile effects, and euphoria. 5-Bromo-DMT was said to be similar to low-dose DMT, but also distinct from it. A 50mg dose was said to be near the limit of what can be physically inhaled. However, it was thought that greater exposure to the drug nonetheless might be able to produce stronger effects. These findings were reported in a Shulgin- or TiHKAL-like style via credible anonymous personal communication with Hamilton Morris and Jason Wallach.

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

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