5-Bromo-DMT

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5-Bromo-DMT

IUPAC name [2-(5-bromo-1H-indol-3-yl)ethyl]dimethylamine
Identifiers
CAS number	17274-65-6^Y
PubChem	360252
ChemSpider	319812^Y
ChEMBL	CHEMBL403031^Y
Jmol-3D images	Image 1 Image 2
SMILES CN(C)CCC1=CNC2=C1C=C(Br)C=C2 CN(C)CCc2cnc1ccc(Br)cc12
InChI InChI=1S/C12H15BrN2/c1-15(2)6-5-9-8-14-12-4-3-10(13)7-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3^Y Key: ATEYZYQLBQUZJE-UHFFFAOYSA-N^Y InChI=1/C12H15BrN2/c1-15(2)6-5-9-8-14-12-4-3-10(13)7-11(9)12/h3-4,7-8,14H,5-6H2,1-2H3 Key: ATEYZYQLBQUZJE-UHFFFAOYAL
Properties
Molecular formula	C₁₂H₁₅N₂Br
Melting point	98-99 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

5-Bromo-DMT (5-bromo-N,N-dimethyltryptamine) is a brominated indole alkaloid found in certain marine invertebrates. It is the 5-bromo analogue of DMT, a hallucinogen found in many plants and animals.^[1] Other naturally occurring 5-substituted analogues of DMT include bufotenin and 5-MeO-DMT, both of which, like DMT, are psychoactive and found in plants and animals. Animal studies on 5-bromo-DMT showed it to produce effects suggestive of sedative and antidepressant activity.^[2]

This compound is soluble in ethanol and methanol. It is found in Verongula rigida (0.00142% dry wt.) and also 5,6-diBr-DMT (0.35% dry wt.) was found as well as seven other alkaloids. 5-Br-DMT caused significant reduction of locomotor activity in the rodent FST model (suggested to indicate a potential sedative action). It did not show any antidepressant activity in either test. ^[3]

References

^ Djura, Peter et al. (1980). "Some Metabolites of the Marine Sponges Smenospongia aurea and Smenospongia (= Polyfibrospongia) echina". Journal of Organic Chemistry 45 (8): 1435–1441. doi:10.1021/jo01296a019.
^ Kochanowska AJ, Rao KV, Childress S, El-Alfy A, Matsumoto RR, Kelly M, Stewart GS, Sufka KJ, Hamann MT (February 2008). "Secondary metabolites from three Florida sponges with antidepressant activity". Journal of Natural Products 71 (2): 186–9. doi:10.1021/np070371u. PMID 18217716.
^ Kochanowska et al. 2008

Tryptamines

2-Methyl-5-HT • 4-Acetoxy-DET • 4-Acetoxy-DiPT • 4-Acetoxy-DMT • 4-Acetoxy-MiPT • 4-AcO-MET • 4-HO-αMT • 4-HO-DiPT • 4-HO-MET • 4-MeO-DMT • 4-Methyl-αET • 4-Methyl-αMT • 4,5-DHP-DMT • 4,5-MDO-DMT • 4,5-MDO-DIPT • 5-Benzyloxytryptamine • 5-Bromo-DMT • 5-Carboxamidotryptamine • 5-Ethoxy-αMT • 5-Fluoro-αMT • 5-HO-αMT • 5-HTP • 5-Ethoxy-DMT • 5-Ethyl-DMT • 5-Fluoro-DMT • 5-Methyl-DMT • 5-Methoxytryptamine • 5-MeO-7,N,N-TMT • 5-Methyl-αET • 5-MeO-αET • 5-MeO-αMT • 5-MeO-DALT • 5-MeO-DET • 5-MeO-DiPT • 5-MeO-DMT • 5-MeO-DPT • 5-MeO-MALT • 5-MeO-MiPT • 5-MeO-NBpBrT • 5,7-Dihydroxytryptamine • 5-(Nonyloxy)tryptamine • 6-Fluoro-αMT • 7-Methyl-αET • 7-Methyl-DMT • αET • αMT • Aeruginascin • AL-37350A • BW-723C86 • Baeocystin • Bufotenidine • Bufotenin • DALT • Desformylflustrabromine • DET • DiPT • DMT • DPT • Ethocybin • EiPT • EMDT • EPT • Ethocin • FGIN-127 • FGIN-143 • Ibogaine • Indorenate • Iprocin • MET • MiPT • MPT • Miprocin • Melatonin • MS-245 • NAS • NMT • Norbaeocystin • Normelatonin • Oxypertine • PiPT • Psilocin • Psilocybin • Rizatriptan • Serotonin • Sumatriptan • Tryptamine • Tryptophan • Yohimbine • Yuremamine • Zolmitriptan

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