3,5-Dimethoxyamphetamine

From Wikipedia, the free encyclopedia
Jump to navigation Jump to search
3,5-Dimethoxyamphetamine
File:3,5-Dimethoxyamphetamine.svg
Clinical data
Other names3,5-DMA; DMA-6
ATC code
  • None
Identifiers
  • 1-(3,5-dimethoxyphenyl)propan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
E number{{#property:P628}}
CompTox Dashboard (EPA)
  • {{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC11H17NO2
Molar mass195.262 g·mol−1
3D model (JSmol)
  • CC(CC1=CC(=CC(=C1)OC)OC)N
  • InChI=1S/C11H17NO2/c1-8(12)4-9-5-10(13-2)7-11(6-9)14-3/h5-8H,4,12H2,1-3H3
  • Key:PDCLPGSYMZLLDX-UHFFFAOYSA-N

3,5-Dimethoxyamphetamine (3,5-DMA), also known as DMA-6, is a drug of the amphetamine family and a positional isomer of dimethoxyamphetamine (DMA).[1] It is the parent structure of the 3C (4-substituted 3,5-dimethoxyamphetamine) family of compounds (also known as 3C-scalines).[1]

In an early study, it showed similar affinity for serotonin receptors as mescaline (3,4,5-trimethoxyphenethylamine) but had more than an order of magnitude lower affinity than DOx (4-substituted 2,5-dimethoxyamphetamine) drugs like DOM, DOET, and DOB.[1][2] However, in a later study, it showed no or very low affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = >10,000 nM), whereas DOB showed high affinity for these receptors (Ki = 32 nM and 64 nM, respectively).[3] 3,5-DMA's effects on monoamine reuptake and efflux have also been studied.[1][4][5][6] It appeared to be weak or inactive as a norepinephrine reuptake inhibitor and norepinephrine releasing agent.[4][5] Likewise, it was a very weak serotonin reuptake inhibitor (IC50Tooltip half-maximal inhibitory concentration = 18,500 nM) and serotonin releasing agent (active at ≥10,000 nM).[6]

3,5-DMA was inactive in substituting for DOM in rodent drug discrimination tests (4–14% appropriate responding for 5–12.5 mg/kg), suggesting that it would not be hallucinogenic in humans.[1][7] However, it has shown other pharmacological effects in mice and with similar potency as mescaline, whereas it was inactive in rats.[8] The effects of 3,5-DMA in humans have not been reported.[1][8] 3,5-DMA has been detected as an adulterant in forensic drug samples.[9] As a positional isomer of 2,5-dimethoxyamphetamine (2,5-DMA; DMA-4), 3,5-DMA is a Schedule I controlled substance in the United States.[1]

A derivative of 3,5-DMA, 4-bromo-3,5-dimethoxyamphetamine (4-Br-3,5-DMA), showed relatively high affinity for the serotonin 5-HT2A and 5-HT2C receptors (Ki = 210 nM and 570 nM, respectively).[3] However, it was not active as a psychedelic at the assessed doses (4–10 mg).[10]

See also

[edit | edit source]

References

[edit | edit source]
  1. ^ a b c d e f g Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  2. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  3. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  4. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  5. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  6. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  7. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  8. ^ a b Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  9. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
  10. ^ Lua error in Module:Citation/CS1/Configuration at line 2172: attempt to index field '?' (a nil value).
[edit | edit source]
Retrieved from "http://70.231.62.181/index.php?title=3,5-Dimethoxyamphetamine&oldid=19741232"